Home Vacation Rentals By Owner In Orleans, MA

Showing 280 Of 296 Vacation Rentals
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Exceptional(17)

$1258.26

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Private Vacation Home

Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the store

Orleans, Massachusetts, United States

Light filled, four bedroom, 2½ bath (plus outdoor shower), fully air-conditioned house with fabulous close-in water views and steps from swimmable private dock. The house is surrounded by water for fantastic panoramic saltwater views and set on a promontory. It also has wonderful gardens and a grove of cedar trees. brThis lovely home overlooks Meeting House Pond whose glimmering salt waters flow to outer Nauset beach, Chatham and beyond. Nearly all windows front tidal meetinghouse pond capturing its awesome dawns and silver moon ascents. Watch fishing boats depart, ducks glide by, hear flocks of geese and gulls call out. Radiant light gilds each room lending special ambiance to a perfect summer retreat. Treasures of this Cape Cod jewel are too numerous to mention but here are a few: brIt’s so pleasant to breakfast, looking at the water, in its sun-drenched country kitchen with attached greenhouse or enjoy the open, waterfront dining room or breakfast on the patio overlooking the waterbrbrbrRelax in its serene living room and gaze at the water and enjoy your surroundings. Dream in the pristine master bedroom to the lull of lapping tides and enjoy the gorgeous water view. On the lower floor, you might like the large, comfortable entertainment center that boasts a large flat screen TV and unique collection of DVD’s. brbrIf feeling energetic, untie your kayaks from the dock and head down river to Pleasant Bay and Chatham’s waters.brbrOn a private road, down a long driveway and hidden from view, all this is to be found a short stroll from the very heart of wonderful East Orleans Village with its famous farm market, shops, gourmet and casual restaurants (including wonderful pizza, dessert, deli and homemade ice cream stand) and so close to Nauset Beach--an easy walk to everything but private enough that you're in another world! A true get-away. Have a glorious vacation!brExtra amenities:br-- Flagstone patio, gas grillbr-- Luxury outdoor shower for both adults and children br-- Convenient, large, separate laundry room with water viewbr-- Charming marina nearby. This IS a Hidden Waterfront Paradise!
Bed 4

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Bath 2

Bath

Sleep 8

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Exceptional(7)

$694.31

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Private Vacation Home

Walk to Skaket Beach, Great Backyard!

Orleans, Massachusetts, United States

Summary:brbr15574 - Set Sail: Walk to Skaket Beach, Great Backyard!brbrbrbrThe Space:brbrConveniently located in Orleans, moments from the shores of Skaket Beach, awaits your idyllic retreat - a quintessential Cape Cod haven. Take a stroll down the road, by going right out of the driveway, to the end of Captain Linnell Rd, and turning left on to Willie Atwood. At the end of the road is a path right to Skaket, the public portion of the beach is to the right. (See photo) This bright cape home exudes timeless charm, boasting a sprawling deck and expansive backyard, perfect for indulging in leisurely afternoons filled with classic yard games like cornhole, beneath the embrace of the Cape's azure skies. Step inside to discover a spacious sanctuary, offering four bedrooms designed to accommodate your every need. With two bedrooms conveniently situated on the first floor, accessibility and comfort intertwine effortlessly within this coastal abode. brbrWhether you yearn for a day of seaside tranquility at Skaket Beach or prefer the allure of local shopping and culinary delights in downtown Orleans, both experiences lie within a short drive from your doorstep, promising an array of unforgettable memories.brbrAwaken to the gentle melody of bird songs as you savor your morning coffee upon the back deck, enveloped by the whispering breeze of Cape Cod's enchanting landscape. Indulge in leisurely family barbecues, as long-lasting memories are made while the aroma of grilled delicacies tantalizes your senses.brbrEmbrace the essence of Cape Cod living, with Skaket Beach beckoning just 0.8 miles away, while the sprawling trails of Nickerson State Park and Kent's Point offer boundless opportunities for exploration, each a mere three miles in opposite directions from your tranquil abode.brbrVenture into downtown Orleans, a mere 1.5 miles away, where a diverse array of restaurants awaits, catering to every palate and age group, ensuring culinary adventures abound.brbrEscape to this cherished Cape Cod retreat, where every moment is imbued with the essence of coastal serenity and familial bliss, promising an unforgettable vacation experience.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10brBedroomsbrTotal 4br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 3 Twins (1 Bunk, and 1 Single)br-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 4 Twins (1 Bunk + 2 Twins)brBathroomsbr-Total 2br-1st Floor: Tub/Shower Combobr-2nd Floor: Tub/Shower CombobrOther Amenities br-Window A/Cbr-WiFibr-TVbr-Washer/Dryer br-Propane Grillbr-Outdoor Showerbr-Fire pitbr-Outdoor Games Provided: Cornholebr-Indoor Fireplace is not for guest use(fines remitted)br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 3 cars maximumbr-C0469112240
Bed 4

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Bath 2

Bath

Sleep 10

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Exceptional(3)

$728.49

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Private Vacation Home

Walk 5 Minutes to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15557 - Beach Break: Walk 5 Minutes to Nauset Beach!brbrbrbrThe Space:brbrNestled within the picturesque coastal enclave of Nauset Heights, where the whisper of the ocean breeze mingles with the melody of crashing waves, awaits your ultimate Beach Break retreat. Situated between the tranquil Nauset Harbor and the renowned Nauset Beach, part of the majestic National Seashore, this hidden gem promises an unforgettable seaside escape.brbrA mere five-minute stroll from the property leads you to the pristine shores of Nauset Beach, a ten-mile expanse of golden sands renowned for its sun-drenched tranquility and thrilling water sports opportunities, from surfing to fishing.brbrStep inside this extraordinary abode to discover a haven of relaxation and coastal charm. The main floor unfolds into a bright and airy living room, where plush sofas invite you to unwind amidst the company of loved ones. Adjacent, a spacious dining area beckons, surrounded by walls of sliding glass doors that seamlessly blend indoor and outdoor living. Venture onto the expansive wrap-around deck, adorned with patio furniture and a convenient propane grill, offering the perfect setting for al fresco dining and sunset soirees.brbrWith over 1,500 square feet of living space, this home comfortably accommodates up to ten guests across four bedrooms. Two queen bedrooms grace the main floor, while upstairs, another queen bedroom awaits, nestled beside a spectacular seating area adorned with vaulted ceilings and oversized windows that flood the space with natural light. The ground floor hosts the fourth bedroom, featuring two sets of twin-over-full bunk beds, ensuring a cozy retreat for the younger members of your party.brbrAdditional amenities, including mini-split A/C, a smart lock for seamless self-check-in, and a refreshing outdoor shower, elevate your stay to unparalleled levels of comfort and convenience. So, kick back, unwind, and savor every moment of your well-deserved Beach Break vacation.brbrHome Details:br-No Pets (fines remitted)br-Sleeps 10br-2 FloorsbrBedroomsbr-Total: 4br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Queen Bedbr-Ground Floor Bedroom: 2 Bunk Beds (Twin over Full)brBathroomsbr-Total: 1 Full Bathroom / 2 Half Bathroomsbr-1st Floor: Full Bathroom w/ Shower/Tub combobr-2nd Floor: Half Bathroombr-Ground Floor: Half BathroombrOther Amenitiesbr-Outdoor Showerbr-Mini-Split A/C Systembr-Smart Lock/Self Check-Inbr-Washer and Dryer (ground floor)br-WiFibr-TV with Cablebr-Fireplace NOT for guest use (fines remitted)br-Foosball Tablebr-Deck with Patio Furniturebr-Propane Grillbr-Private Yardbr-Walk 5 Mins (0.3 mile) to Nauset Beachbr-please note outdoor amenities are seasonally availablebr-There is parking for a maximum of 3 cars.br-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-C0222242240brbrbrbrThe Neighborhood:brbrOceanside
Bed 4

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Bath 2

Bath

Sleep 10

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$219.91

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Cottage

Petite Antique, location, location, location

Orleans, Massachusetts, United States

br**Location Location Location**brbrNestled in the historic district of Orleans, our charming little cottage is perfectly situated for those looking to experience the best of Cape Cod. We are conveniently close to a variety of stunning beaches, including Rock Harbor and Bay beaches such as Skaket Beach, Boat Meadow Beach, and First Encounter to name a few. For those who prefer the wild Atlantic Ocean, Nauset Beach, Nauset Light Beach, and Coast Guard Beach are just a short drive away. Additionally, fresh water ponds are within easy reach, providing ample opportunities for swimming and relaxation.brbrThe closest bay beach, Dyer Prence, is merely 0.3 miles away—a pleasant 10-minute walk, making it easy to enjoy leisurely days by the water. For those who prefer to explore, we are just 0.8 miles from the center of Orleans, where you can find local seafood restaurants, charming ice cream shops, and unique, locally owned boutiques. The Cape Cod rail trail bike path abuts our property, offering a scenic route for biking enthusiasts and nature lovers alike.brbrFor adventure seekers, right around the corner from the cottage, you can embark on a fishing charter from Rock Harbor, where you can reel in some of the local catch while enjoying the beautiful coastal views. Just a 15-minute drive away, Chatham Harbor provides access to The Beach Comber boat shuttle, which takes you to some of the most pristine and uncrowded Atlantic Ocean beaches on the East Coast. Keep your eyes peeled—you might even spot a shark fin or, more commonly, some playful seals enjoying their natural habitat. Downtown Chatham also offers an array of beautiful shops, candy stores and restaurants, you can easily fill a day here! brbrIf you’re in the mood for exploration, a day trip to Provincetown is only a 30 to 45-minute drive away. This vibrant seaside village is known for its character, vibrant and artistic spirit, and an array of amazing restaurants. Whether you choose to embark on a thrilling whale watch or simply stroll through the charming streets filled with art galleries and shops, Provincetown offers a delightful and very unique experience.brbrFor those looking to venture further, we are approximately 30 minutes from Hyannis, where you can catch a ferry to the picturesque islands of Nantucket and Martha's Vineyard—a must-do day trip that is sure to create lasting memories.brbrbr**Accommodations and Amenities**brbrPlease note that the downstairs bedroom is quite small featuring two twin beds (only) that can be converted into a king if needed; however, it is important to mention that there is not a separate king bed and two twin beds. The downstairs bedroom is cozy, making it a snug retreat after a day of exploration.brbrWe are also dog-friendly and would be happy to consider your furry companions, as we love dogs! This topic is open for discussion. Our little family resides full-time in the barn at the back of the property, along with our adorable dog, Charlie girl, who adds to the warm, welcoming atmosphere to our home.brbrMore information available upon request, so please feel free to reach out via email with any questions you may have. We look forward to welcoming you to our beautiful corner of Cape Cod!brbrbrbr
Bed 2

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Bath 1

Bath

Sleep 4

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$333.9

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Cottage

Wonderful 2-bedroom cottage with AC and Heat in charming Orleans, MA!

Orleans, Massachusetts, United States

Discover this 2-bedroom cottage in Orleans. Guests find a welcoming space featuring a queen bed in the main room and 2 twin beds in the guest room plus a living room with a comfy couch. The bathroom offers a refreshing shower and a handy hair dryer completelyrenovated in 2025. Stay comfortable year-round with heating and AC throughout the cottage. Whether relaxing indoors or planning your day, this awesome spot provides a superb base for your getaway. It’s easy to see why you’ll feel right at home here. We are conveniently located less than 2 miles to Nauset Beach, multiple lakes,and just close to the towns center with multiple large supermarkets, restaurants and other conveniences. We also have a semi private path walking distance to Rodgers Cove (salt water bay that connects to the Town Cove). Its a great close by location for kayaking, canoeing and other water activities. Its more or less a Peninsula with water all around the location. We have a working fireplace, charcoal grill, small out door deck, and an attached laundry room on the back of the home. There are other cottages within this cottage community, but you will find that the home has adequate privacy. This cottage has been rented out on other websites for years with an excellent review history. We aim to provide a wonderful vacation experience. This home is small, but has vaulted ceilings in the living room that give you the feeling that you are in a much larger space.
Bed 2

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Sleep 5

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Exceptional(6)

$436.32

/ Nightly
Private Vacation Home

OSLOT--Desirable Home Near Nauset Beach with Ocean Views

Orleans, Massachusetts, United States

Location! Location! Location!brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrTraditional Cape in the desirable Nauset Heights area of Orleans. Ocean views. Short walk to Nauset Beach. Sleeps 7-8.brbrThe first floor features a bright dining room with ocean view, comfortable living room with 50 Roku tv, well-equipped kitchen with dishwasher, full bath with shower and tub, and two bedrooms, including one with access to the screened porch.brbrThe second floor has ocean views from each room, including vibrant skies during sunrises and sunsets! This floor offers a bedroom with one queen bed and one twin bed, a full bathroom with shower, and a sitting room with cocktail table, chairs, daybed, and a 43 Roku TV.brbrThere is a nice grass backyard with an ocean view and bunnies as frequent visitors, a private grass front yard, screened porch, a garage for storing your bikes and kayaks only, a slate patio with gas grill, and an enclosed outdoor shower. The garage contains plenty of beach chairs, umbrellas, and a wagon for you to use.brbrBedrooms: First Floor: Bedroom #1; 1 Full, Bedroom #2; 2 Twin. Second Floor; Bedroom #3; 1 Queen and 1 Twin. Sitting Room; 1 Twin Day Bed.brbrAmenities include: Five window air conditioning units (all bedrooms, living room and upstairs sitting room), wireless internet, two smart televisions( both able to accept most streaming services and also providing 100+ streaming channels from Xfinity), one upstairs and one down, a smart washer that automatically dispenses healthy environment detergent with no need to bring or add your own, dryer, gas and charcoal grills, enclosed outdoor shower, a firepit, and plenty of beach chairs. brbrSheets and towels are not included.brbrLocation: Conveniently located between Nauset Beach's main entrance (3 minute drive) and Priscilla's Landing, and just short half mile away from both. And it's a shorter distance to the north end of Nauset Beach via Callanan's Pass, and a minute or two more via the Nauset Heights Association stair access to the inlet and Little Beach. brbrNauset Beach was recently named in the top ten in a listing of The 100 Most Breathtaking Views in America. Its consistently high rankings are due in part to its 10-mile beach, its dunes, and its views of the Atlantic ocean. It's a great place to take pictures, and the sunrises and sunsets offer dramatic colors Nauset's waves are legendary and afford an incredible ocean beach experience for swimmers surfers and beachgoers. Fishermen enjoy surfcasting for stripers and bluefish. The main entrance to Nauset Beach has ample parking, as well as food trucks, restrooms and showers.brbrPriscilla's Landing, which is located on a cove within the Nauset Harbor estuary, offers calm waters for swimming, kayaking, canoeing, and paddleboarding. You can walk along the shoreline from Priscilla's Landing past the Nauset Heights Association's stair access to another quiet beach area for swimming and paddling, and from there to the north end of the main Nauset Beach area and its larger ocean waves. The parking at Priscilla's Landing is limited, so it is super convenient to be able to walk from the house.brbr* Additional Fees: $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services fee; all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO PETSbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and Children)br* PARKING FOR 2 VEHICLES - DO NOT PARK ON THE GRASSbr* SHEETS AND TOWELS ARE NOT PROVIDED, available to rent from local linen company, we are happy to provide informationbrbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC OSLOT
Bed 3

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Bath 2

Bath

Sleep 7

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Exceptional(35)

$457.8

/ Nightly
Private Vacation Home

Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach

Orleans, Massachusetts, United States

This is the perfect home for your family get away. Recently remodeled and improved in 2023 with two new baths and in 2016 with a new kitchen, open floor plan, new master bedroom addition, and new screened porch. brbrLocated at the end of a cul de sac and situated on 1.3 acres, this spacious 4 bedroom, 2.5 bath home provides wonderful peace and quiet, but with all the conveniences you desire, such as whole house Wi-Fi, AC units, satellite/streaming HDTV, and nearby coffee houses, brewery, restaurants, and markets. Best of all, it's just a 0.6 mile stroll from the white sands and sunsets of Skaket Beach! You can walk to the beach using a private sand path in just 15 minutes and you'll be able to enjoy the calmest part of Skaket Beach - the best beach on Cape Cod. brbrThe home is convenient to everything Orleans and the outer cape have to offer as well. Ride just 0.5 miles to the Cape Cod Rail Trail bike path. Drive to the ponds, freshwater fishing and hiking of Nickerson State Park - just 1.5 miles away. Drive to the surf of the Cape Cod National Seashore - just 9 miles away. Golf, fantastic restaurants, delicious ice cream are all nearby. brbrThis inviting home easily sleeps 10 people and has plenty of space for two families and even your extended family. The first floor offers an open living space with a large family room, brand new kitchen, dining room, 1.5 updated baths, and brand new large screened porch. There is plenty of comfortable seating and tables for calm breakfasts, seafood dinners, and family game nights. There is also plenty of access to the outside so you can enjoy the calm of the 1.3 acre yard. brbrThe kitchen was fully remodeled in 2016 with new cabinets and a peninsula for eating. It has new appliances, including a refrigerator with in-door water/ice, a dishwasher, microwave oven, and stove/oven. br brThe main family room has a cathedral ceiling with exposed beams. It offers a big screen HDTV and opens to side deck and a screened in porch with a chest of board games. brbrThe dining room has a large table that seats 8. It opens to a large screened porch with an additional table that seats 6 and for fresh-air dining and relaxation. brbrThe first floor also has: br1. A master bed room (21'x13') with adjoining bathroom that provides the convenience of first floor living. It has a king size bed, flat screen HDTV, full size bath remodeled in 2023 with a wonderfully powerful shower, and air-conditioning. br2. A second bedroom that includes two twin beds, flat screen HDTV, and an in-room air conditioner. This bedroom also has easy access to the full size bath. br3. A large (16'x16') screened porch was added in 2016. It has a cathedral ceiling, is easily accessible from the kitchen and dining room and provides great views of the yard.br4. A half bath and laundry room off the family room was remideled in 2023.br5. A second family area offers a fireplace, game-size coffee table, and a futon couch for additional sleeping options. brbrThe second floor offers two large, private bedrooms with air-conditioning. The first has a queen size bed, two twin beds, and a flat screen HDTV. The second bedroom has a king size bed and flat screen HDTV. Both bedrooms access a full bathroom with a large whirlpool tub. brbrThe 1.3 acre property gives adults the privacy to connect with nature, relax and enjoy the early morning or evening sea breezes. The yard gives children plenty of room to run, play yard games, and explore in a private, safe setting. Enjoy the outdoor shower to experience the beautiful blue sky and morning birds or for a convenient clean up when you return from the beach!
Bed 4

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Bath 2

Bath

Sleep 10

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Exceptional(11)

$2753.95

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Private Vacation Home

White Crest: 009-O Private Orleans resort with water views, heated pool/spa & fire pit

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky Properties.brbrPrivate Orleans resort with water views, heated pool & spabrbr4 beds/4 full, 2 half baths, sleeps 14brRents Friday to Friday during peak seasonbrLinens includedbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrYour multi-generational or multi-family summer vacation has found its home.brbrEnjoy panoramic views of Nauset Inlet and the Atlantic Ocean beyond from this beautifully remodeled Orleans home. The owners have added a heated salt water pool, hot tub, gas fire pit and outdoor grilling area, all with splendid views. Walk less than 3 minutes to your beach and launch the owner provided kayaks to explore Nauset Inlet or Town Cove.brbrInside, on the main level, the vaulted ceilings and open floor plan create a grand sense of light and space. You will find a chef inspired kitchen with high-end, stainless steel appliances including a wine refrigerator and gas stove. The kitchen is equipped to entertain and cook for a crowd. There are mesmerizing views from the large dining room table and the living room, which walk out to the large deck and pool area. This home offers sleeping for up to 14 guests in four bedrooms, each with a private bath plus two half-baths. The main level features a generous primary bedroom suite with a king size bed, beautiful views of the water and a luxurious en-suite bath. There is a jetted tub, over-sized shower, dual vanities and a walk in closet.brbrUpstairs are two bedrooms, each with a private bath and private balconies overlooking the water. The first bedroom provides a king size bed plus a day bed, perfect for the family with a small child. The other bedroom features another king size bed and private bath. Above the garage in the west wing of the home you'll find a giant bunk room, a wonderful space for the kids. There are 3 twin-over full size bunk beds and two twin size beds plus a private bath, TV, Xbox and charging stations. And it's away from the rest of the home so children can have their own space and do their own thing.brbrThe completely refinished lower level is the media/game room. Enjoy the full bar and Foosball table, pool table, gaming table, plus large screen TV and comfy lounge seating. It's a perfect spot to relax in case the weather doesn't cooperate. And of course the home is equipped with all the modern amenities you'd expect: central air conditioning, Wi-Fi, charging stations, cable TV, and a washer and dryer. Each room provides high-end linens and towels, no need to bring your own.brbrThis property provides the accommodations you need to bring the whole family and enjoy your own private mini-resort. Whether it's spending the day at the pool, on the beach, out on the water on the kayaks or playing corn-hole in the yard, the entire family can find something to enjoy. And once the day is done, marvel at the beautiful starry nights while dining al fresco on the deck. Bask in the glow from the cheery fire pit. Or slip into the soothing hot tub and gaze out over Nauset Inlet and ocean views. Please note: pool and hot tub are open Memorial Day - Columbus Day.brbrPlease enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%.brbrThis property offers a three night minimum stay during select weeks in May – June & Sept, Oct. & November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived.brbrBe sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky! ®
Bed 4

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Bath 4

Bath

Sleep 14

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Exceptional(15)

$625.5

/ Nightly
Cottage

Beautifully remodeled cottage near the beach with central AC, gas grill & lawn

Orleans, Massachusetts, United States

The Quintessential Cape CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCompletely renovated, this stunning Cape Cod vacation cottage is ideal for groups or small families looking for a breezy stay near Orleans, MA. The interior is completely renovated with brand new furnishings throughout, providing guests with the ultimate vacation experience. Take advantage of the gas grill in the private yard and host entertaining barbecues on a summer night. There is also an outdoor dining table for four, which will make meals alfresco a breeze.brbrGather around the coffee table in the living room and pull out any of the board games provided for a fun family evening at home! Or stream a favorite series on the smart TV with streaming services. No matter what you decide to do, this home is all about entertainment and comfort. The fully equipped kitchen is complete with stainless steel appliances and every cookware you could need to prepare delicious snacks for your day trips to the beach or full-course meals. You'll love being located in Orleans, right off of Route 6 for easy travel and access to any part of the Cape you wish to visit during your stay.brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 2

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Bath 1

Bath

Sleep 4

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Exceptional(1)

$981.14

/ Nightly
Private Vacation Home

Enchanting waterfront home with two decks, grill, kayaks, board games, W/D, & AC

Orleans, Massachusetts, United States

Sailor SanctuarybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrA unique getaway awaits you on the shoreline of Pleasant Bay. Built like a ship, this light-filled home boasts two decks, a ship-like window, and of course, sweeping water views. Spend your days watching passer sailors, hammocking, gliding across the water on the provided kayaks, hosting cookouts with the help of the gas grill, and dining alfresco on one of the two decks. When you aren't hanging out in this peaceful space, head for a walk on one of the area's walking trails, or head a quick 1.5 miles away toward Nauset Beach. Nickerson State Park, Nauset Lighthouse, Cranberry Valley Golf Course, and the Mass Audubon Wellfleet Bay Wildlife Sanctuary are all less than 10 miles away. brbrFull of sunlight and plush furnishings, the home's main living area boasts an excellent space to read and visit with the people you love. Steps from here, the full kitchen presents any chef's dream with its center island, ample meal prep space, and updated appliances. brbrWith four bedrooms to sprawl out in, rest assured that everyone's comfort is catered to. Additional interior amenities include a washer/dryer, board games, central air-conditioning, and internet access.brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brAlthough the occupancy is eight, two out of the eight must be children as the twin beds are only suited for kids.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 4

Bed

Bath 4

Bath

Sleep 6

Sleeps

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Exceptional(2)

$522.61

/ Nightly
Private Vacation Home

Quiet home near Pilgrim Lake with deck, W/D, AC, games, & large yard

Orleans, Massachusetts, United States

Great White Cape EscapebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to the picturesque town of Orleans, and unwind in this spacious house close to the Pilgrim Lake Recreation & Conservation Area. Ideal for families or groups, this Cape Cod retreat offers a plethora of amenities, including a washer/dryer, central AC, and internet access, ensuring a comfortable and stress-free stay.brbrStep outside onto the deck or patio, complete with cozy furniture and a gas grill, perfect for enjoying outdoor meals or basking in the sun. Just a short walk to Pilgrim Lake, this home is a haven for beach lovers and water enthusiasts looking to explore nearby beaches or try activities like swimming and stand-up paddleboarding. A paddleboard along with two sea kayaks are available for guest use.brbrInside, the house features a well-equipped kitchen with modern appliances, a welcoming living room with a TV, and multiple levels providing ample space for relaxation. The twin bedroom upstairs features the longer twin XL size beds, which can be positioned together to create a third king bed. Whether you're unwinding after a day of exploring or curling up with a good book from the selection provided, this home offers everything you need for a memorable vacation.brbrConveniently located near restaurants, shops, and local attractions such as Skaket Beach, Nauset Beach and the town of Chatham, there's plenty to see and do during your stay. Whether you're interested in beachcombing, bird watching, or simply relaxing by the ocean, this charming location caters to all interests. Book your stay at this lovely house and start planning your Cape Cod getaway today!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
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$853.73

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Private Vacation Home

Beautifully Renovated Home Near Pleasant Bay

Orleans, Massachusetts, United States

This home has been painstakingly renovated with love and thoughtful improvements for tenants to create unforgettable memories in this wonderful retreat! Air conditioning and hardwood floors throughout only adds to the many great attributes this property has to offer.brbrAs you enter, you will be greeted by a cozy and inviting atmosphere on the first floor, featuring a relaxing den, a fantastic gourmet kitchen, spacious living room and dining area, full bathroom and a lovely guest bedroom.brbrThe second floor boasts comfortable bedrooms, each offering a peaceful retreat after a day of exploration. The large master bedroom and master bathroom also includes a separate work area for those who can not completely escape their job. This bedroom is filled with plenty of natural sunlight. The second bedroom is equally as spacious and beautiful. There is a full bathroom with tub just outside this bedroom.brbrThe walkout lower level offers another family room with exercise bike and large flat screen television with sound system and a new day bed with trundle (2 twin beds). There is also a separate room with washer and dryer.brbrThe enjoyment continues outside where you will be able to enjoy bocce ball, corn hole, and badminton just off the large furnished deck with sectional seating, fire pit and chaise lounge chairs. There is also a wonderful hot tub to relax in and an enclosed outdoor shower.brbrBEDS: First Floor; Bedroom 1 - 1 Queen. Second Floor; Bedroom 2 - 1 Queen, Master Bedroom - 1 King. Lower Walk-out Level; Twin Day Bed with Twin Trundle.brbrAMENITIES: Mini Split wall units on all three floors, wireless internet with Xfinity, DeLonghi coffee maker, gas range, washer and dryer, 3 televisions with streaming (Den, Living Room and Lower Level), gas grill, 4 beach chairs and a beach cart.brbrLOCATION: This home is nestled within a nice South Orleans neighborhood and just over a half mile from Pleasant Bay. If you prefer, it would be under a minute to drive where you can park on the street for free. This is a great area with beach for sunning, swimming, boating, kayaking, paddle boarding and more. Nauset Beach is 5.8 miles away, and Skaket Beach is 5.3 miles away. Fresh water ponds, Crystal Lake and Pilgrim Lake are both under 3 miles away. It is 3.7 miles from the center of Orleans, and 5.6 miles from the center of Chatham.brbr***The owners of this property are looking for someone who will love and care for this exceptional home as much as they do.***brbr* Additional fees: $220 non-refundable reservation fee; $30 damage protection fee; guest services fee; all applicable taxesbrbr* SUNDAY TO SUNDAY RENTALbr* NO SMOKINGbr* NO PETSbr* FREE WIFI br* OCCUPANCY: 8 PEOPLE TOTAL (adults and children)br* PARKING FOR 3 VEHICLESbr* SHEETS AND TOWELS ARE NOT INCLUDED, available to rent from local linen company, we are happy to provide informationbrbr***RENT 32 DAYS OR MORE AND ELIMINATE ALL TAXES***brbrbr****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area.brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental!brbrAs a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!
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Exceptional(14)

$582.14

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Private Vacation Home

Spacious home with huge deck & tree-lined yard, grill, & WiFi - great location

Orleans, Massachusetts, United States

Spinnaker TrailbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrYou couldn't ask for a better location for your next, or first, Cape Cod escape than this comfortable, four-bedroom home. With easy access to the beach, boating, hiking, biking, state parks, golf, restaurants, shops, and charming towns, you’ll be spoiled for choice when it comes to activities, but with both indoor and outdoor spaces so lovely, you may spend most of your time at home. Start the day with coffee and end it with a cocktail on your huge back deck, overlooking the expansive lawn and tree-lined property. The Adirondack chairs and patio just downstairs offer another quiet spot for contemplation or a good book. At dinnertime, fire up the gas grill for a family cookout.brbrInside, you’ll find high ceilings, hardwood floors, and lots of natural light thanks to plenty of picture windows. The open, well-equipped kitchen features a full suite of stainless steel appliances and all the counter space and cabinetry you could need. With kitchen island seating and a dining room just around the corner, there’s plenty of room at mealtime. When it’s time to relax at home, several comfy gathering spots beckon, including a family room and a formal living room on the main floor, along with a bonus room and TV den in the basement. If you’ve got any remote work on your plate, the dedicated office space on the upstairs landing, plus the free WiFi, make completing it a breeze. At bedtime, four well-appointed rooms await, with one on the bottom floor, the primary suite on the first floor, and the remaining two upstairs. brbrTHINGS TO KNOWbrStreaming services are available with guest accounts.brThe fireplace is not available for guest use.brbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Select Dates for Price

Inviting family escape with sunroom, deck, W/D & easy access to Nauset Beach

Orleans, Massachusetts, United States

Coastal LandingbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to Coastal Landing, your inviting Cape Cod retreat tucked away in the picturesque Briar Spring Hills neighborhood. This lovingly maintained home blends classic coastal style with thoughtful updates, just 2 miles from Nauset Beach and near the tranquil waters of Pochet Inlet.brbrStep inside to a beautiful open layout with hardwood floors, fine finish carpentry, and a lovely staircase that frames the airy foyer. Light streams in from skylights above the upstairs hallway, where a cozy reading chair sits beneath the natural glow and offers a perfect spot for your morning coffee or a good book.brbrOn the main level, the recently renovated kitchen features a spacious breakfast bar island and flows seamlessly into a dining room with beamed ceilings, setting the stage for relaxed family meals and easy conversation. Just off the dining room is a delightful sunroom, perfect for reading or lounging, plus a convenient half bath. The welcoming living room features French doors, hardwood floors, and plenty of space to unwind together. The main bedroom offers a beautiful private bath along with a dedicated vanity sink and dressing area for added comfort.brbrUpstairs, three bright bedrooms offer ample space for everyone, including one that combines a bedroom and den with a comfortable sofa, television, and airy skylights—a perfect spot for kids or teens to relax and play.brbrEnjoy summer evenings and sunny afternoons on the private deck, or use the grill while guests enjoy the yard. Wash away the salty sand in the outdoor shower after a day at the beach.brbrWith WiFi, cable television, and a washer and dryer, all the comforts of home are at your fingertips. Coastal Landing is close to restaurants, ice cream shops, mini golf, and bike trails, making it the perfect launchpad for Cape Cod adventures and memories to last a lifetime!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
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$718.15

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Private Vacation Home

Renovated 3 Bedroom with Beautiful Marsh Views

Orleans, Massachusetts, United States

Summary:brbrUnder 1 mile to Skaket BeachbrbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company.brbrbrbrSituated at the end of a private road, Sun Glow overlooks Little Namskaket Marsh and Cape Cod Bay in the distance. Conveniently located between Skaket Beach (0.9 miles) and Rock Harbor (1.3 miles), and only 1.2 miles from Orleans center. Only 0.6 miles to the Cape Cod Rail Trail, a 27.5 mile-long asphalt trail for biking, running and walking. brbrbrbrThe starring feature of Sun Glow is its large deck overlooking the marsh. Completely rebuilt in 2019, its beautiful mahogany top rail and cable railing maximize the marsh view! This is the perfect spot to enjoy the view of the bay or one of Cape Cod's spectacular sunsets, hence the house name. The marsh is home to an abundance of wildlife. Depending on the time of day, you might get a glimpse of a hawk in flight, a White Egret or a Great Blue Heron. There is plenty of outdoor seating and a propane grill so you can enjoy meals outside or just lounge with a book in one of the Adirondack chairs. The enclosed breezeway is another great spot for reading and relaxing, and kids will love the large, grassy yard. The location is private and very safe! brbrbrbrInside, the home has been renovated with new AC added, fresh paint and furnishings, and updated kitchen. You will enjoy full AC throughout with brand new mini split units throughout the house, as well as an updated kitchen with brand new floors and quartz countertops. There are three bedrooms and two full bathrooms, each with tub/shower. Downstairs there is a queen bedroom and upstairs there is a king bedroom with brand new memory foam mattress and a kids room with bunk bed and two twins. The house sleeps 8 comfortably.brbrbrbrWith its modern amenities and unique location, Sun Glow is a very special place to get away from it all!brbrbrbrLayout of Bedrooms & Bathrooms:brbrMain LevelbrbrBedroom 1 - queen brbrFull bath with showerbrbrUpper LevelbrbrBedroom 2 - king bed with new memory foam mattressbrbrBedroom 3 - two twins and bunk bed brbrFull bath with tub/shower combobrbrbrbr**Typically renters bring their own sheets, towels etc. Please inquire if you are interested in having linens delivered to the home for an additional fee.**brbrbrbrOther Things to Note:brbr-
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Exceptional(58)

$1500.11

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Private Vacation Home

5 BR/4 bath w/heated pool .2 miles to Nauset Beach

Orleans, Massachusetts, United States

A truly special home that feels like a resort, and is just a stone's throw from popular Nauset Beach. No paying for parking, or leaving the house early to fight for a parking spot. brbrConveniently located on Beach Road, steps to the beach, but set back on a very private and peaceful acre of mature trees and magical garden blooms. Spend your days relaxing by the heated gunite pool, or on one of the many decks the home offers. brbrWith 3000 sq ft, and 2 master bedrooms, there is plenty of room for everyone! Gather in the large kitchen/living room, with vaulted ceilings and picture windows, or in the sky lit sun-room. The living room, family room, sun-room and 3 of the 5 bedrooms all have Anderson sliding doors that lead to decks overlooking the gardens and pool area.brbrThe main level has 3 bedrooms and 3 baths - two master bedrooms (one queen and one king), a full bath in the hallway and a queen bedroom. The main level also has an open living/dining/kitchen area, a spacious mudroom and relaxing sunroom. Sliders from the living room, both master bedrooms and the sunroom lead to multi levels of deck overlooking the gardens and pool area.brbrThe lower level has 1 queen bedroom and a kids room with 2 bunkbeds (4 twins), a full bath and family room with tv. Sliders from the family room and queen bedroom lead to patios overlooking the gardens and pool area.brbr The kitchen has been stocked with everything you will need to cook the perfect family meal, and plenty of room for everyone to help! brbrWe have thought of everything so you don't have to - just unpack and unwind. Your rental includes all linens and towels, toilet paper, paper towels, soap, detergent, beach toys, beach chairs and more. brbrThis amazing home is available for weekly summer rentals (July/August) and 3 night minimum stays May, June, September and October! Be one of the lucky families to enjoy a special vacation that is just a short walk from Nauset Beach.brbrOur home is available to families only, with adults over the age of 25 - no young adult groups, please.brbrWhile we love our furry friends, we do not allow pets at this home. brbrWeekly rentals in July-August are Saturday to Saturday only for check in/check out. There is a 3 night minimum for all other months, without restrictions on the check in/check out days.brbrDrive or bike 7 minutes (3 miles) into the town of Orleans for groceries, shops and restaurants or just a couple of minutes (1 mile) to Nauset Farms, Barley Neck Inn and Sundae School Ice Cream, as well as several quaint shops and restaurants.brbrEnjoy a week on the Elbow, exploring the shops and restaurants in Orleans, and visit neighboring towns like Chatham , Wellfleet and Provincetown.
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$780.78

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Private Vacation Home

Nauset Perch: 006-OO East Orleans Contemporary—Easy Access to Nauset Beach!

Orleans, Massachusetts, United States

This home is professionally managed by Pretty Picky Properties.br brNauset Perch: East Orleans Contemporary—Easy Access to Nauset Beach!brbrSleeps 8 in 3 bedroomsbrRents Friday to Friday in July and AugustbrLinens included, beds madebrbrRATES REDUCEDbrbrThis multi-level contemporary retreat invites you to unwind with light-filled interiors and lush, wild landscapes framed by expansive windows. The home has multiple levels of living space to capture the best of the surrounding natural beauty, and because it sits up on a hill, you'll love the ocean breezes that waft through the house!brbrThe stunning top-floor great room features a remarkable 270-degree panorama, with views of the Atlantic Ocean to the east and Nauset Harbor to the north, as far up as the Nauset Lighthouse. The room has a huge couch to spread out on, a dining area that seats eight, a TV-viewing area with loveseats, a fully equipped kitchen, and an outdoor deck. Truly a great room!brbrBelow it, the second level sports the primary bedroom suite with a king bed, full bath and private porch. The main entrance level has a large foyer and full bathroom. The lower level houses the other two bedrooms, one with a queen bed and convertible chair (twin), the other with 2 traditional twin beds plus a convertible chair (twin). There is a shared bath on this level as well.brbrThe owners are working hard this winter to connect what has been a separate garage directly to the house, and to convert it to a large den and loft, offering the greater privacy of a second large, shared space. They are also adding an outdoor shower, a favorite feature of many Cape renters.brbrLocated in coveted Nauset Heights, the house and property are set on a dead-end private road lot. The wild natural habitat surrounding the home provides an ideal setting for relaxation and privacy, and it's a favorite hangout for birds of all types (they especially love the tall Metasequoia tree). It's just a short walk to Nauset Beach, one of Cape Cod's most loved, offering endless opportunities for outdoor fun.brbrEnjoy coastal living with private access to Nauset Beach via an association staircase, plus easy access to paddleboarding, biking, hiking, and the shops and restaurants of Orleans. Savor the abundant sun and cool ocean air at The Perch!brbrPlease enter your travel dates for up-to-date pricing. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $215.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for vacation rental on Cape Cod.brbrIt's your vacation. Get Picky! ®
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