Vacation Rentals By Owner In Orleans, MA

$795.03

5-bedroom Cape with a pool and yard games.

Orleans, Massachusetts, United States

Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent). Three rooms on the first floor adjacent to the living room, kitchen, and dining room. The master bedroom has an attached private bathroom. The two smaller rooms share a bathroom in the main hall. The second floor has two larger bedrooms with recently renovated bathroom. Spacious living room with 70” TV, a couch and loveseat. Kitchen has all stainless steal appliances - 36” French door fridge, large OTR microwave, and electric glass top stove and oven. A toaster, coffee maker, and air fryer are available. Ductless mini-splits heat and cool each bedroom, which are individually regulated. The backyard is spacious, approximately 10,000 square feet, and has an inground pool and various yard games. The front door has a keyless entry. The code will be sent to you the day of your check-in. I will be available to help guests at any time. Write or call for support if you have any questions. Private dead-end road with access to Pleasant Bay. Town landing on route 28 is less than a mile away. Freshwater ponds in nearby conservation land with trails. The Captain’s Golf Course is two minutes away - the course has two par 72, 18 hole courses. Pleasant Bay Community boating offers a variety of programs for children and adults. You may not want to leave the pool side, but you may want to walk down to Pleasant Bay or a fresh water pond for a dip. Drive ten minutes to either downtown Chatham or Orleans Center. If your a cyclist or mountain biker, take a spin to the CC Rail Trail and Nickerson State Park. There is one bath towel per guest available. We do not provide pool or beach towels. Our home is NOT part of the Quanset Harbor Club (home association). You have access to the street and conservation land trails for walking but our guests do not have rights to the beach and landing at the end of Lake Drive. There is, however, a town landing at the end of Quanset Road, Portanimicut Road, and on route 28 (~1/4 mile from the house).

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$599.37

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Private Vacation Home

Pondfront, 1 Mile to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15582 - Calm Waters: Pondfront, 1.4 Miles to Nauset Beach!brbrbrbrThe Space:brbrAlong the serene shores of Uncle Harvey’s Pond, this Orleans retreat offers a perfect blend of relaxation and adventure. Just 1.4 miles from the iconic Nauset Beach and a short mile from the charming East Orleans Main Street, this three-bedroom, two-bathroom home invites you to experience Cape Cod at its finest.brbrbrbrInside, the newly renovated upstairs suite accommodates four and boasts a private full bath, while two cozy bedrooms and an additional bathroom on the first floor provide comfortable arrangements for up to eight guests. Sunlight dances through the windows, framing water views that soothe the soul.brbrbrbrBegin your day with coffee from Whisk or a hearty breakfast at The Rail, then grab sandwiches from Nauset Farms and head to the beach to enjoy the waves—or try your hand at surfing! For a more leisurely pace, launch kayaks directly from the pond, or unwind on the expansive deck, soaking in the peaceful views.brbrbrbrEvenings beckon with simple pleasures: stargazing from the deck, enjoying ice cream from Smitty’s, or savoring a quiet night in this thoughtfully designed home. With water views, seamless indoor-outdoor living, and easy access to the best of Orleans, this retreat is more than a destination—it’s an invitation to reconnect with nature, family, and yourself.brbrbrbrExperience the magic of Cape Cod. Book your waterfront escape today and let the adventure begin.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 8brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 Queen Bedbrbr1st Floor Bedroom: 2 Twin Bedsbrbr-2nd Floor Bedroom: 1 Queen Bed, 2 Twin BedsbrbrBathroomsbrbr-Total 2brbr-1st Floor: Full Bath w/ Showerbrbr-2nd Floor: Full Bath w/ Shower and Tubbrbr-Split System A/Cbrbr-WiFibrbr-Cable TVbrbr-Washer/Dryer brbr-Propane Grillbrbr-Outdoor Showerbrbr-Direct access to Uncle Harvey's Pondbrbr-3 Kayaks w/ life jackets brbr-Air Hockey Tablebrbr-Indoor Fireplaces are not for guest use(fines remitted)brbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 3 cars maximumbrbr-C0277742240brbrbrbrThe Neighborhood:brbrOceanside

3

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2

Bath

8

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$2747.99

/ Nightly

Private Vacation Home

Pochet Point Estate 056-O: Pochet Estate with Nauset Beach Access, Pool & Panoramic Views

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky Properties.brbrPochet Point Estate with Nauset Beach Access, Pool & Panoramic ViewsbrbrNEW Listing for 2026!brbrSleeps 16brRents Friday to Friday during summer weeksbrLinens includedbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrWelcome to your East Orleans retreat—an extraordinary water-view estate in the coveted Pochet neighborhood, offering refined coastal living just steps from Nauset Beach. This Patrick Ahearn designed seven-bedroom, seven full and-two half-bath home spans three levels plus a pool house of luxurious living, thoughtfully designed for gathering, relaxation, and coastal adventure.brbrThe main level features a gourmet kitchen with high-end appliances, a spacious island, and seamless flow to multiple interior and exterior dining areas. Gather in the elegant great room or one of several inviting lounge spaces, each offering comfortable style and tranquil views of Pochet Inlet and the surrounding salt marsh.brbrThere are 5 bedroom suites each with a King bed and private bath. There is one bedroom on the main level and an additional four bedroom suites on the second level. The third floor offers two family-friendly rooms—one with two twin beds and another with two sets of twin-over-twin bunks—ideal for kids or groups. There is also a full bathroom on the third level as well. brbrStep outside to your private resort setting: an oversized heated gunite saltwater pool, hot tub, and expansive pool deck designed for sun-soaked days and evening relaxation by the wood-burning fire pit. The magnificent Atlantic is your backdrop from the pool area. The ocean serenades you with the consistent calming wave action on the nearby shore. The pool house adds a layer of fun and function, complete with a game room, full bath, and laundry.brbrFrom the backyard, a private neighborhood boardwalk leads you through protected dunes to world-famous Nauset Beach—a breathtaking walk to one of Cape Cod's most iconic stretches of sand and surf. From the boardwalk you are accessing a secluded part of the beach to the south the public beach area. Plenty of space to set up camp and enjoy the rhythm of the Atlantic Ocean. brbrPerfect for large families or multi-generational groups, this estate combines modern luxury, coastal charm, and unbeatable location—the ultimate East Orleans escape.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. 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 this site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky! ®

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$945.64

/ Nightly

Apartment

Walk to Town, Fully Renovated!

Orleans, Massachusetts, United States

Summary:brbr15531 - Maplewood Manor: Walk to Town, Fully Renovated!brbrbrbrThe Space:brbrDiscover the charm of Orleans in this thoughtfully renovated vacation home, blending historic character with modern luxury. Located just 2.4 miles from Skaket Beach and 2.6 miles from Nauset Beach, this spacious retreat is the perfect haven for families and friends. Stroll 0.3 miles to Main Street for dining, shopping, and bike rentals, or explore the nearby Town Cove for boating and kayaking adventures.brbrInside, the home comfortably sleeps 12, accommodating up to 12 guests across six bedrooms and a lofted space. The first-floor bedroom offers a king bed, while the second floor features three more bedrooms, including a king bed bedroom, a full bed bedroom and two twin-bed options. The third-floor is a great suite for kids, with a murphy bed that sleeps two, a futon, and 2 bedrooms, one with a full and one with a twin bed.brbrRelax in the fully fenced yard, perfect for kids to roam while you grill on the gas BBQ or gather around the fire pit under the stars. Indoors, enjoy a Viking stove for culinary creations, central AC for ultimate comfort, and a soaking tub for unwinding after sun-soaked beach days. Walk to La Bella Vita for Italian fare or The Corner Store for their famous burritos, and end your evening with a nightcap on the lantern-lit front porch.brbrYour perfect Orleans getaway is waiting. Book today and make memories that last a lifetime!brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 12brBedroomsbr-Total 6br-1st Floor Bedroom: 1 King Bed w/ Ensuite bathroombr-2nd Floor Bedroom: 1 Full Bed w/ Ensuite bathroombr-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 2 Twin Bedsbr-3rd Floor Bedroom: 1 Full Bedbr-3rd Floor Bedroom: 1 Twin Bedbr-3rd Floor Lofted Space: 1 Full Murphy BedbrBathroomsbr-Total 3.5brOther Amenities br-Central ACbr-WiFibr-Cable TVbr-Washer/Dryer br-Gas Grillbr-Fire pitbr-Indoor Fireplaces are 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 4 cars maximumbr-C0196972240br

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$927.91

/ Nightly

Private Vacation Home

Pleasant Bay Beachfront Property Plus!

Orleans, Massachusetts, United States

The owners refer to this one-of-a-kind property as Pleasant Plus. This unique beachfront home and certified wildlife habitat is located on Big Pleasant Bay with spectacular panoramic water and big sky views from the Atlantic Nauset barrier beach to the golf course at Chatham's Eastward Ho! Country Club.brbrSet on a bluff, the main house is an amazing, white-washed, full Post and Beam design. The first floor offers a family-friendly open floor plan with oversized fully equipped kitchen, dining area and living room with vaulted ceiling and open loft. There is one half bathroom in the foyer and one full bathroom with tub/shower at the end of a center hall, as well as two guest bedrooms; one with a queen bed and one with two twin beds.brbrStep out of the family room onto a full-length deck looking south onto the fall/winter kaleidoscope of down-Cape weather, certified natural wildlife habitat, and relentless local and migratory bird activity.brbrOn the second floor you will find a stunning master bedroom with king-sized bed where you will wake each day overlooking the breathtaking vista. This floor also features a separate full bathroom with shower, a third guest bedroom with one double bed and two small twin beds, and a fully tech-equipped work from vacation office setting and/or kid-friendly entertainment area for reading, creating, gaming or just relaxing.brbrThe lower walkout-to-beach level features a large glass-walled indoor bathroom to accommodate guest and beach-goers alike, as well as an all-weather (above freezing) outdoor shower with view of Strong Island.brbrStairs descend south from the Bay side of the house to the 1100 square foot boathouse/party house built directly on the private sandy beach where guests can isolate and commune with the Bay's nature and beauty up close and personal at any time, and in any weather.brbrPleasant+'s isolation from public activity (down a 1/3 mile private lane, into a gated cul-de-sac) make the property an ideal cathartic getaway from the realities of urban living. Unique features of this all-season home make it possible to experience the wonders of Lower Cape Cod's fall and winter natural and wildlife beauty, all the while remaining engaged and connected as remote work-from-home responsibilities may require.brbrAmenities include: Panoramic view of Pleasant Bay from all living areas, central heating and air conditioning, high-speed wired and WiFi internet service, full home office/WFH setting, first floor washer and dryer, 3 smart TVs with live streaming service, DVD/VHS player, telephone, light duty laser printer, gas grill, Keurig and drip coffee makers, enclosed outdoor shower, seasonal outdoor furniture, kayak, dinghy, beach chairs and recliners, sporting and aquatic gear, etc. Linens are provided for prime season rentals. For all other weeks, tenants can bring their own linens or rent them.brbrbr* Additional Fees:br- $300 Cleaning Fee. br- $220 Non-Refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Feebr- All Applicable Taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO PETS (no exceptions)br* NO SMOKINGbr* OCCUPANCY: 10 (adults and children)br* PARKING FOR 4 VEHICLESbr* Sheets and towels provided on all weeks between May 30 - September 26, 2026. Linens are not included on any off-season stays. Tenants may bring their own or rent for $300.00.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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$904.37

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Private Vacation Home

Spacious Game Room Close to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15529 - Beach Bend: Spacious Game Room Close to Nauset Beach!brbrbrbrThe Space:brbrThis exquisitely renovated home offers an idyllic retreat for up to 12 guests, boasting expansive outdoor spaces, luxurious accommodations, and an unbeatable location for an unforgettable vacation experience. Situated on a sprawling lot, both the front and back yards enchant with their picturesque beauty, providing three distinct outdoor seating areas for moments of relaxation and connection with nature.brbrEmbark on a leisurely stroll to Gilman Landing, a serene nature and kayak access point nestled on the shores of Pleasant Bay, where mornings are best spent savoring coffee amidst the tranquility of the coastal landscape. For endless sandy shores, Nauset Beach awaits less than 2 miles away, while Beach Road beckons with its array of charming shops and eateries, including Nauset Farms, The Barley Neck Inn, and Smitty's for irresistible ice cream delights.brbrThe allure of this vacation home extends beyond its enviable location, offering a spacious first floor that seamlessly merges a modern kitchen, plush seating area, and separate dining space, perfect for shared meals and cherished moments. Step onto the covered porch adorned with classic rocking chairs for shaded relaxation, or retreat to the second deck area featuring a large outdoor sofa and propane grill for alfresco dining under the stars.brbrThe first floor also hosts a serene Master bedroom with a king bed and en suite bathroom, while upstairs reveals three additional bedrooms, including a second Master with a sun-drenched walk-out balcony, a spacious bedroom with two queen beds and two twin beds, ideal for families, and a cozy retreat with a king bed. Entertainment abounds with a TV area and foosball table, ensuring fun for all ages.brbrCentral A/C throughout the home promises respite from the summer heat, ensuring comfort and relaxation throughout your stay. With its perfect blend of luxury and convenience in an unbeatable location, this home offers everything you need for a truly unforgettable Cape Cod getaway.brbrHome Details: br-No pets (fines remitted)br-Sleeps 12br-2 floorsbrBedroomsbr-Total: 4br-Master bedroom 1: 1 king bed, en suite full bathroom, 1st floorbr-Master bedroom 2 : 1 king bed, en suite full bathroom, 2nd floorbr-3rd bedroom: 1 king bed, 2nd floorbr-4th bedroom: 2nd Floor Kid's Suite with 2 queen beds and 2 twin beds, game roombrBathroomsbr-Total: 3.5br-1st floor: Full bath ensuite with shower and separate tubbr-2nd floor: full bath ensuite with showerbr-2nd floor: full bathroombr-1st floor: half bathbrOther Amenitiesbr-Central A/Cbr-Smart TV with Cablebr-WIFIbr-Washer and Dryer in 2nd floor laundry roombr-Outdoor Showerbr-Private Yardbr-Gas Grillbr-please note outdoor amenities are available seasonallybr-There is parking for a maximum of 4 carsbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-C0137542240brbrbrbrThe Neighborhood:brbrOceanside

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$463.04

/ Nightly

Condo

Walk to the association beach at Little Pleasant Bay from this updated cozy cottage

Orleans, Massachusetts, United States

Walk to the association beach at Little Pleasant Bay from this updated cozy cottage. Sleeping 4 - this rental has 2 upstairs bedrooms (2 queens) and 1 full bath. AC throughout with a slimline unit in the living room and central ac upstairs. Relax with your morning coffee on the deck before heading to the association beach for the day. After your day at the beach, you can grill your favorite meal and relax on the deck or enjoy the front lawn with some games but be sure to take a short drive to Skaket Beach and enjoy the beautiful sunset to end the day. You can also bring the family dog, as this home is dog friendly (1 dog only); so, ask your agent for details-$150 fee will apply. Parking for 2 cars. This rental is a shared property, the main house will have caretakers on site. Call us at Chatham Rentals and let us help you plan your stay.

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$590.07

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Private Vacation Home

Quaint Cottage Close to Skaket Beach (1912)

Orleans, Massachusetts, United States

If you are looking for the perfect location on Cape Cod, this charming Orleans cottage delivers on every level. Situated just moments from the calm waters of Skaket Beach, guests can enjoy the famous tidal flats that create a safe, unique environment for small children and a tranquil retreat for beach lovers. Outdoor enthusiasts will also appreciate being less than a mile from the Cape Cod Rail Trail, the renowned bike path that spans the length of the Cape. While the neighborhood offers a quiet, private community feel, you are only minutes away from the vibrant center of Orleans, where famous restaurants, cozy coffee shops, and eclectic boutiques await.brbrThe interior of the cottage is designed for comfort and ease, featuring an open layout that connects a cozy living area to an updated, eat-in kitchen. The family room is furnished with a comfortable new sofa, creating an inviting space to relax after a day in the sun. The main floor houses two bedrooms—one with a queen-sized bed and another with two twins—providing a convenient single-level living experience. For additional sleeping space, the lower level walk-out basement includes a double bed. brbrOutdoor living is a standout highlight of this property. The primary bedroom opens directly onto a large, sun-drenched deck overlooking a beautifully landscaped lawn. The backyard functions as a private oasis, fully outfitted with deck furniture for the whole family and a gas grill for classic summer barbecues. Tucked away in the yard is a lovely outdoor shower, a quintessential Cape Cod experience that makes rinsing off after the beach feel like a spa visit. The home’s central location in the elbow of the Cape provides effortless access to Nauset Beach, Rock Harbor, and the protected beauty of the National Seashore, making it an ideal base for exploring Chatham or Provincetown. brbrThe home offers all of the most requested amenities such as Central AC, wireless internet, and Roku for streaming all your favorite shows! *Sorry, no pets…no exceptions. 3 night minimum available with an added cleaning fee. 7 nights or more, the cleaning is included. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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Sleeps

$333.71

/ Nightly

Private Vacation Home

Cozy Home in Quiet & Convenient Area (1140)

Orleans, Massachusetts, United States

Tucked away on a peaceful wooded lot, this comfortable and pet-friendly 3-bedroom, 2-bath home offers the perfect balance of tranquility and convenience. Located just minutes from the Cape Cod Rail Trail, the center of Orleans, and beautiful Skaket Beach, you’ll be close to everything while still enjoying a private, quiet setting.brbrInside, the home features an updated kitchen with dining area, a welcoming living room, and a first-floor bedroom with two twin beds. Upstairs, you’ll find two additional bedrooms—one with a king bed and the other with a queen plus two twins—providing flexible sleeping arrangements for up to 8 guests. Two full bathrooms, Wi-Fi, and air conditioning window units add comfort and ease to your stay.brbrStep outside to enjoy the spacious yard, perfect for summer fun and evening cookouts. Fire up your choice of a gas or charcoal grill, relax on the deck, or rinse off in the enclosed outdoor shower after a day at the beach.brbrWith its convenient location and relaxed coastal charm, this home is ideal for families, friends, and even four-legged companions looking to make the most of their Cape Cod getaway.br br2 night minimums available off season with an added cleaning fee. Weekly rentals include cleaning fee. brPlease note: An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$565.47

/ Nightly

Private Vacation Home

Expansive Home by Orleans Town Landing (1086)

Orleans, Massachusetts, United States

This spacious and comfortable 2-story contemporary home sits on a wooded lot within a short distance to a public boat ramp to launch on Pleasant Bay and minutes away from Nauset, Skaket and Pleasant Bay beaches. brbrWith four bedrooms and three baths, it sleeps up to 8 effortlessly. The first level features a living room, family room, fully equipped kitchen, and two bedrooms, each with a queen-sized bed. The second floor offers another full bath along with the two additional bedrooms, one with a queen-sized bed and the second with two twins. Amenities include central A/C, wireless internet, washer/dryer, outdoor shower, an outdoor deck with dining table and a gas grill for summer barbecues. brbrAn administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$354.61

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Private Vacation Home

Pet-Friendly Orleans Ranch (1560)

Orleans, Massachusetts, United States

This cozy 2 bedroom 2 bath ranch sits on a wooded lot in the heart of East Orleans. It is located a short drive to Nauset beach as well as the restaurants and shops of East Orleans and Orleans Center. The 2 bedrooms feature a Queen and a brand new King with en suite bath and the main bathroom was updated recently. The living room has an alternative sleeping area with a full sleeper sofa and 65 flat screen TV. Amenities like 2 A/C units, WiFi and Extended Cable TV make this a great little rental for any summer vacation. The deck features a gas grill for great summer barbeques. It is also pet friendly dog pen in back yard, so bring Fido or Fluffy! 3 night minimums available with and added cleaning fee. 7 nights or more include cleaning. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$312.83

/ Nightly

Apartment

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.

Orleans, Massachusetts, United States

This apartment has all the amenities you will need. Orleans is a very nice town with Restaurants and shopping. We also have both Nauset Beach for the waves and body surfing along with Skaket Beach for small waves. Come and experience one of the best towns on Cape Cod!

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$1163.3

/ Nightly

Private Vacation Home

Waterfront retreat, private yet minutes to town and beach. Sleeps 7, 3 bedrooms

Orleans, Massachusetts, United States

Wake up to stunning, uninterrupted views of calm, crystal-clear waters in this beautifully updated 3-bedroom home, sleeping 7. Nestled in a private neighborhood just minutes from Nauset Beach and town, this serene retreat offers the ultimate waterfront experience.brbrStep out your door, and down the bank stairs and launch your kayak directly from the property. Wake up, grab your coffee and lounge on the deck while watching the seals glide by. Unwind with cocktails in hand while enjoying the Weber grill, lounge chairs, and outdoor dining area – all perfectly positioned to take in breathtaking sunsets.br Inside, this bright and airy home features an open-concept living, dining, and granite kitchen, ideal for entertaining. The first-floor primary bedroom with AC, ensures easy living, while upstairs, two bedrooms with AC provide a comfortable retreat for everyone. Additional highlights include 2 full baths, a refreshing outdoor shower with changing area, private front and backyard, bank stairs to the water and plenty of indoor and outdoor areas to lounge.brbrBook your slice of paradise today and make this private waterfront haven your home base for unforgettable summer memories!

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$613.12

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Private Vacation Home

Nestled by Nauset

Orleans, Massachusetts, United States

Beautiful newly renovated Cape home nestled in a quiet neighborhood, close to Nauset Beach and Orleans Town Center with wonderful restaurants and shops. Enjoy a quiet evening on the front porch or relax on the back deck in the midst of nature. The home is comprised of a King Bedroom featuring double French doors, and two Queen bedrooms offering rest and relaxation after a day at the beach. There are two full bathrooms with walk-in showers and a private outdoor shower. Make memories in the large Family room with vaulted ceilings and windows with natural light illuminating the home. Enjoy the tranquility of a second living room with a decorative fireplace. There is a formal dining room, adjacent to the kitchen for enjoying Family meals. There are two desks and chairs for those who need to need to work whilst enjoying their getaway. Laundy facilities, free Wifi and foosball table are among the amenities in the home. A private driveway can accommodate an RV and there is a 30-amp outlet for RV or electric car charging. The home is close to some of the most beautiful beaches on Cape Cod.

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$494.72

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Private Vacation Home

Private Retreat on Pilgrim Lake! (1507)

Orleans, Massachusetts, United States

This serene private retreat is the perfect place to relax and enjoy the beauty of nature. The waterfront landing on Pilgrim Lake is ideal for swimming, jumping off a swim float, kayaking, paddle boarding, fishing or birdwatching. The kitchen is well-equipped, making entertaining a breeze. The lakeside deck has ample, comfortable seating, market umbrellas, flower boxes, and a fresh herb garden. Enjoy a sparkling sunrise on the lake, a sizzling BBQ on the deck, or a magical moonrise in the evening. At the end of a perfect beach day, the outdoor shower is great for rinsing-off. brbrInside, the house is designed for comfort and ease. The primary bedroom offers a king bed, a full bathroom (with a 12-inch high mini-tub perfect for easy toddler bathing, and a separate baby tub is available upon request), TV, and access to a private deck with a lake view. The two other bedrooms have a queen bed and 2 twin beds, respectively. Each bedroom has a full-size closet, bench and convenient clothing hooks. There is also an extra sleeping area for two, off the living room in the entry way, with a full daybed, allowing for 8 total guests. brbrAdditional features of this property include lovely flower gardens, premium TV and Wi-Fi services. Quiet air conditioning is available throughout. A washer and dryer are conveniently located on the 1st floor and a standby generator ensures peace of mind during inclement weather. The home is close to beautiful beaches, parks, events, galleries and fine restaurants. Food shopping is just minutes away. For ultimate convenient recreation, you can rent kayaks and paddleboards and even arrange for delivery and pick-ups, right at the lakefront! brbrAn administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$333.79

/ Nightly

Cottage

Pets Welcome Near Town & Bike Trail (1471)

Orleans, Massachusetts, United States

Located beside Cedar Pond which is great for fishing, this home offers all of the privacy and convenience you could ask for while enjoying your Cape Cod vacation. Walk to Main Street and the Bike Trail in less than a half mile or bike to beautiful Skaket Beach - just a mile away! This home has a very private setting with only one other home on the small family friendly street. The interior features a large living room with Cable TV and sliding door to the deck, full kitchen, dining area and a full, renovated bath. The primary bedroom offers a queen sized bed and window a/c unit, the second bedroom has another queen sized bed and window a/c unit, and the third bedroom features a set bunk beds. Enjoy evening barbecues on the deck complete with a gas grill! Other amenities include wireless internet and an enclosed outdoor shower. Don't forget to bring your family pet as dogs and cats are welcome! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$940.08

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Private Vacation Home

Custom Cape Home Near Pleasant Bay & PahWah Pond (1580)

Orleans, Massachusetts, United States

Enjoy your next Cape Cod vacation from this custom 4 bedroom, 3 and a half bath home! It is in a quiet area of South Orleans only a quarter mile to Pah Wah Landing Conservation area on Little Pleasant Bay and a short walk through the conservation area to the secluded beach. Little Pleasant Bay has great kayaking and boating from nearby Portanimicut Launch and the conservation area is great for nature walks! This beautiful rental home is perfect for your summer vacation. brbrThe first level features an open floor plan with a beautiful bright and airy kitchen and breakfast bar, dining area, and family room with soaring ceilings and windows all around which illuminate the space with natural light. Also on the first floor is a primary bedroom with a queen-sized bed and ensuite bath with a shower, an office/den with a futon and desk with a slider that opens to a deck, a half bath, mudroom with front loading washer/dryer, and bar sink. Easy access to the the back deck or garage is off this space. The second level features three bedrooms (a second primary with a queen sized bed and ensuite bath and cozy sitting space, one with two twin sized beds, one with a queen sized pullout sleeper sofa) and a full bath with a shower. Enjoy the beautifully finished enclosed outdoor shower, great for rinsing off after a day at the beach. The large back deck has furniture for outdoor dining and a gas grill for summer barbeques. Central A/C and WiFi internet round out the excellent amenities offered here. brbrNauset and Skaket Beaches are both a short drive away and as is Orleans town center with shops and restaurants! Additionally, Wequassett Resort is about a 5 minute car ride away and down town Chatham is only 5 minutes further! There is driveway parking for 4 cars. Owner will consider a discount for 2 or more consecutive weeks, Just ask! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$423.26

/ Nightly

Private Vacation Home

Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215)

Orleans, Massachusetts, United States

A close distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor furniture. brbrA galley, eat-in kitchen seats four and the comfortable TV room, adjacent to the kitchen, has sliders onto the deck for easy access to the barbeque. The large living room has a flat screen TV and the dining area seats 6. A twin bed room and full bathroom with tub and shower finish off the first floor. The second floor has another full bath with tub and shower and lots of counter space. There are 2 bedrooms, one with 2 twin beds and the other with a Queen bed. Lots of windows give this home a bright and airy feel. Central A/C and WiFi complete this home's list of comfortable amenities. brbrPlease note: An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

Bed

Bath

Sleeps

$645.32

/ Nightly

Private Vacation Home

Beautifully Decorated 3BR Cape - Less than .5 miles to Beach! (1945)

Orleans, Massachusetts, United States

Beautifully decorated, recently updated home less than .5 miles to popular Skaket Beach on Cape Cod Bay! The first level offers a light, bright open kitchen, dining and living area with gorgeous vaulted ceilings. There is a cute sunporch with comfortable furniture for relaxing with family and friends. The first level also offers two bedrooms, one with two twin sized beds and the second with a queen sized bed, as well as a full bath with tub/shower combination. Upstairs is a large Primary Bedroom suite, complete with king bed and private bath. Conveniently located close to the center of town and near the bike path. Spend the evening gathered on the patio complete with outdoor furniture and gas grill. Great amenities include washer/dryer, wireless internet, 4 built in wall a/c units to cool the whole house and an enclosed outdoor shower - perfect for rinsing off after a day on Skaket Beach!! Click the Book Now button today to secure your week at this beautiful rental! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own. Sunday to Sunday rental.

Bed

Bath

Sleeps

$435.73

/ Nightly

Condo

Refurbished Cottage with Views of Town Cove (1038)

Orleans, Massachusetts, United States

Two free lobsters included! This recently renovated 2 bedroom, 1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. brbrThe cottage has lovely grounds and gardens to enjoy, as well as a spacious deck, complete with a gas grill, to relax and enjoy a summer barbeque. The kitchen is recently renovated with granite countertops and new, stainless appliances. The bathroom has also been fully renovated. A recently added addition boasts a Queen primary bedroom while the second bedroom has two twin sized beds. Amenities include Central A/C, new 50 flat screen TV, premium cable service with HBO, WIFI, Netflix and private relaxing area! Extras include high-end beach chairs, umbrella, and clamming rakes and basket! brbrAn administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens from a vendor or bring their own.

2

Bed

1

Bath

4

Sleeps

Vacation Rentals By Owner In Orleans, MA

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