Vacation Home Rentals By Owner In Orleans, MA

$1098.5

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

Orleans, Massachusetts, United States

Summary:brbrSailor SanctuarybrbrbrbrThe Space: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. Full 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. With 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. bThings to Know/b Check-in time: 4:00 PM. Check-out time: 10:00 AM. All 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. No smoking is permitted anywhere on the premises. Although the occupancy is eight, two out of the eight must be children as the twin beds are only suited for kids.

4

Bed

5

Bath

6

Sleeps

$441.43

/ Nightly

Private Vacation Home

Tonset Treasure with Bunk House

Orleans, Massachusetts, United States

Charming East Orleans cottage with farmer's porch and bonus bunkhouse is just minutes from Nauset and Skaket beaches! This updated home is also across the street from the Ice House and Reuben's Pond Conservation Area and Trail and just 1/3 mile to Asa's Landing and Town Cove. Enter through the front porch to the main level which offers a cozy living room, separate dining room, updated eat in kitchen with access to the back porch and large, private fenced back yard.Three bedrooms and a full bath on the upper level and a second full bath on the main level. The detached bunkhouse offers additional sleeping with a bunkbed, cozy seating, a full bathroom and AC (no heat). Beautifully landscaped yard with a large patio with dining table and gas grill for enjoying outdoor meals. Fire Pit surrounded by comfortable adirondack chairs to enjoy on cool nights! Fully enclosed outdoor shower. First floor Washer/Dryer. All 3 full bathrooms with walk-in showers.brbr***Dogs allowed with permission of owner. No Cats unfortunately.***

Bed

Bath

Sleeps

$851.45

/ Nightly

Private Vacation Home

Peaceful and private vacation rental on the pond!

Orleans, Massachusetts, United States

Peaceful and private vacation rental on the pond! This charming 3 bedroom (king, queen, full), 3 bathroom home in Orleans has a great sunny open space for the whole family to relax in. The living room offers beautiful views of the pond, with oversized windows and skylights filling the room with sunshine. Both a TV room and a den allows everyone to spread out and get comfortable. Upstairs brings you to 2 bedrooms (King, full) that share a full bath. The 3rd bedroom is a guest suite found over the garage, that offers privacy with its own staircase just off the kitchen. Central AC and wireless internet to keep you cool and connected on those hot summer days. The views of Uncle Israel's Pond from virtually every room, are tranquil and lovely. While the pond is not suited for swimming, there are 2 kayaks on the property to use, or you can even rent paddle boards. This rental includes a Welcome Bag for tenants staying in season. This reusable tote includes your paper and cleaning products for your stay, compliments of the owner. Call us at Chatham Rentals and let us help you plan your stay.

3

Bed

3

Bath

6

Sleeps

$474.86

/ Nightly

Private Vacation Home

Cozy Cottage Walk to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15586 - Quarterdeck: Cozy Cottage, Walk to Nauset Beach!brbrbrbrThe Space:brbrJust a 0.2 miles walk to Nauset Beach, this single-level retreat welcomes you to Cape Cod. brAble to be rented with two other studio cottages or separately, at Quarterdeck all the charms of Cape Cod await. Listen to the crash of waves right from your deck as you enjoy your morning coffee. Take a leisurely stroll to Nauset Beach and spend your afternoons with the sand and sun.brbrEnjoy the wraparound deck, where you’ll find peek-a-boo ocean views. The home features a fully equipped kitchen, a cozy living area for relaxation, and comfortable bedrooms designed for restful nights. brbrStart your day with a leisurely brunch at The Rail, just 1.4 miles away, or grab a perfectly brewed coffee at Whisk. After a sun-soaked day at the beach, enjoy a laid-back evening cocktail at Barley Neck, a local gem nearby. Back home, let the salty breeze lull you into relaxation as your furry friend lounges by your side.brbrWith water views, beach access just a short stroll away, and the charm of Orleans at your doorstep, this home sets the stage for unforgettable moments.brbrDon’t wait—secure your slice of Cape Cod paradise today and start counting the days until your escape!brbrCan be rented with other homes on the property:br15585 - Ocean Charmer (Main House + Studios)br15587 - Sea Wind (Studio)br15588 - Beach Rose (Studio)brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6brBedroomsbr-Total 3br-1st Floor Bedroom: Queen Bedbr-1st Floor Bedroom: Queen Bedbr-1st Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 1br-1st Floor Bath: Full, Tub/Shower CombobrOther Amenities br-Window Unit ACs in Bedroomsbr-WiFibr-Smart TVbr-Streaming Servicebr-Washer/Dryer br-Propane Grillbr-Rinse station (unenclosed outdoor shower)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 2 cars maximumbr-C0179082240br

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Bath

Sleeps

$616.84

/ Nightly

Private Vacation Home

3 Cottages, Walk to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15585 - Beach Charmer: 3 Cottages, Walk to Nauset Beach!brbrbrbrThe Space:brbrEscape to Orleans, where this charming, dog-friendly vacation compound invites you to embrace Cape Cod’s magic. Just a 0.2 miles walk to Nauset Beach, this single-level retreat with additional studio spaces offers effortless coastal living with the sound of waves as your soundtrack.brbrThe layout of this property features a main home with full kitchen, 3 bedrooms, and 1 bath. There is also a duplex- each side is a 1 room studio with a queen bed and twin bed, TV, full bathroom and kitchenette. This set-up is great for big groups!brbrEnjoy the wraparound deck, where you’ll find peek-a-boo ocean views and plenty of space to sip morning coffee or savor evening cocktails. Inside the main home, the open layout ensures a welcoming, sunlit ambiance. The home features a fully equipped kitchen, a cozy living area for relaxation, and comfortable bedrooms designed for restful nights. The studio apartments ensure everyone has their own space to retreat to for relaxation. Few stairs from the driveway mean easy access for everyone.brbrStart your day with a leisurely brunch at The Rail, just 1.4 miles away, or grab a perfectly brewed coffee at Whisk. After a sun-soaked day at the beach, enjoy a laid-back evening cocktail at Barley Neck, a local gem nearby. Back home, let the salty breeze lull you into relaxation as your furry friend lounges by your side.brbrWith water views, beach access just a short stroll away, and the charm of Orleans at your doorstep, this home sets the stage for unforgettable moments.brbrDon’t wait—secure your slice of Cape Cod paradise today and start counting the days until your escape!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 12brBedroomsbr-Total 5brMain Housebr-1st Floor Bedroom: Queen Bedbr-1st Floor Bedroom: Queen Bedbr-1st Floor Bedroom: 2 Twin BedsbrStudio (Left)br-1st Floor Bedroom: 1 Queen + 1 TwinbrStudio (Right)br-1st Floor Bedroom: 1 Queen + 1 TwinbrBathroomsbr-Total 3brMain Housebr-1st Floor Bath: Full, Tub/Shower CombobrStudio (Left)br-1st Floor Bath: Full, Tub/Shower CombobrStudio (Right)br-1st Floor Bath: Full, Tub/Shower CombobrOther Amenities br-Window Units in Bedroomsbr-WiFibr-Smart TVbr-Streaming Servicebr-Washer/Dryer br-Propane Grillbr-Rinse Stationbr-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-C0179082240

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Bath

Sleeps

$1590.57

/ Nightly

Private Vacation Home

Orleans Resort Style Living with Pool and Hot Tub

Orleans, Massachusetts, United States

With multiple separate entry points this property is perfect for larger or multi-generational groups. Each home has private entries and are connected by a covered walkway. Enter the front home into the living/dining area with kitchenette. Queen bedroom 1 is accessible from the front entry and has a private entry as well. Through the kitchenette you will find a full bath with shower and queen bedroom 2. On the 2nd floor is the loft living area with sofa bed, full bath with shower and bedroom 3 with king. Exit front house from back door and cross the covered walkway to the back house. Enter through the screened porch into open living, dining, kitchen area. Beautifully updated kitchen & dining area easily seats 12. Full bath w shower/tub and queen bedroom 4 on first floor with access to deck and pool via sliding glass door. There is a second side entry to this unit in the living area with quick access to second floor stairs. Second floor has full bath with shower, bedroom 5 with twin beds and bedroom 6 with queen. There is a gorgeous heated pool and New Hot Tub for 2026 Season!!at the back of the property and large patio with stone fireplace at the side of the two homes for easy outdoor living space. Air conditioned with window units in bedrooms and mini splits in front house living spaces. Ideal East Orleans location with the Barley Neck Inn across the street and a short stroll to East Orleans Village for ice cream, Nauset Farms & boutique shopping. 1.5 miles to Nauset Beach and Meeting House Pond nearby for kayaking and boat cruises. Bathrooms all recently updatedbrbr**Sunday to Sunday Rental**

6

Bed

4

Bath

12

Sleeps

$1083.4

/ Nightly

Private Vacation Home

Liberty: 030-O Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky PropertiesbrbrBrand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike TrailbrbrSleeps 10 in 4 bedrooms plus a bonus roombrRents from Friday to Friday in Peak SeasonbrLinens included, beds madebrPool is open Memorial Day to Columbus DaybrbrWelcome to “Liberty” a newly constructed home near downtown Orleans and convenient to Skaket and Nauset Beaches. This luxurious home features all new furnishings and décor, a heated saltwater pool and over 4,000 square feet of living area over three levels.br brThe main level features soaring paneled ceilings in the main living area. The state-of-the-art kitchen is adjacent with a sizable island. The dining room is also in this area for easy prep and service of meals. There's a cozy sunroom off the back of the main level as well for additional lounging and relaxation space. The primary bedroom is just off the kitchen and features a king-size bed, TV and a luxurious private bath. brbrUpstairs, there are two bedrooms, one with a king-size bed and one with 2 full beds. There's a shared bath up here with a shower/tub combo. The 4th bedroom is up a separate flight of stairs and has a king-size bed plus a private bathroom.brbrThe Lower level is expansive and has a movie room area, wet bar, full bath and easy access to the pool deck. There is also a king bed on the lower level for additional sleeping. The pool area has ample lounging area and of course a warm saltwater pool for use.br brHead out on foot or by bike and in moments you'll be in downtown Orleans for dining, coffee, and shopping. The bike trail intersection is 0.4 miles from the house. Or maybe it's a beach day! Skaket Beach on the bay is 1.5 miles or maybe the rolling waves of Nauset Beach is your fancy! Head 4 miles east for the open Atlantic.brbrVacation at Liberty!brbrThis luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning.brbrPlease enter your travel dates 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 14.45%.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky! ®

4

Bed

3

Bath

10

Sleeps

$562.48

/ Nightly

Private Vacation Home

3 Mi to Nauset Beach! Family Home w/ Private Yard

Orleans, Massachusetts, United States

Centrally Located | Spacious Sunroom w/ Outdoor Porch & Patio brbrThe coast is calling, and this cozy Orleans vacation rental is the answer! Perfect for family getaways and summer escapes. Enjoy sun filled days at Skaket and Nauset Beach. Walk to an Orleans Firebirds baseball game or enjoy dinner and shopping in town. End your evenings relaxing on the patio. Secure your stay today!brbr-- THE PROPERTY --brbrC0581592240brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bed, 1 twin cotbr- Bedroom 3: 1 king bedbr- Bedroom 4 (Office): 1 full sleeper sofa brbrINDOOR LIVINGbr- Cozy living spacesbr- Board gamesbr- 6-person dining tablebr- Home office w/ dedicated workspacebr- Large sunroom w/ abundance of natural light (opens to backyard)br- Closet (large enough for portable crib)br- Bathtubs in both bathroomsbrbrOUTDOOR LIVINGbr- Deck w/ seating & gas grillbr- Patio w/ dining tablebr- Spacious yard w/ gardenbrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasher, toasterbr- Single-serve coffee maker (coffee provided)br- Cooking basics, dishware/flatwarebr- SpicesbrbrACCESSIBILITYbr- 3-story home, 3 steps required to enterbr- 1st-floor bedroom & full bathroombrbrPARKINGbr- Garage (1 vehicle)br- Driveway (3 vehicles)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Less than 1 mile to Orleans Town Center (shopping, restaurants & Cape Cod Bike Trail access)br- 10 Minute walk to Nauset Middle School (home field of the Orleans Firebirds) offers tennis/pickle ball courts and playgroundsbr- 2 miles to Nickerson State Parkbr- 1 mile to Crystal Lakebr- 2 miles to Skaket Beach, 3 miles to Nauset Beach & Rock Harbor br- 4 miles to Captain's Public Golf Coursebr- 8 miles to Chatham & 27 miles to Provincetownbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The fireplaces are not available for guest usebr- This 3-story home requires 3 steps to enter; it features a bedroom and a full bathroom on the 1st floor

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Bath

Sleeps

$587.47

/ Nightly

Private Vacation Home

Short drive to town and popular beaches!

Orleans, Massachusetts, United States

Summary:brbr15578 - The Salty Hare: Short drive to town and popular beaches!brbrbrbrThe Space:brbrTruly in the heart of Orleans, right around the corner from the Cape Cod Rail Trail (less than a mile), and only a whisper away from the coveted shores of Skaket Beach, The Salty Hare beckons with timeless allure. This tastefully restored home exudes an aura of coastal elegance, and promises a rejuvenating escape from the bustle of everyday life.brbrbrbrStep inside to discover a harmonious blend of historic charm and contemporary comfort. The updated kitchen, a culinary haven bathed in natural light, invites delicious creations, while the cozy wrap-around deck offers an idyllic setting for savoring morning coffee amidst lush greenery.brbrbrbrIndulge in moments of relaxation in the deep claw-foot tub of the tiled bathroom, a sanctuary where old-world elegance meets modern convenience. For balmy summer days, rejoice in the recent addition of mini splits, ensuring optimal comfort year-round.brbrbrbrVenture just minutes away to Skaket Beach, where the sun-kissed sands set the stage for leisurely strolls and sunset soirées. Upon returning, immerse yourself in the serenity of the outdoor shower, enveloped by the splendor of nature.brbrbrbrAs evening descends, embrace the art of outdoor living on the back deck, where barbecues unfold against a backdrop of birdsong and rustling leaves. With an array of dining options mere minutes away, including the acclaimed Hog Island Brewery and The Beacon Room, culinary delights are always within reach.brbrbrbrWhether seeking seaside serenity or vibrant local experiences, The Salty Hare offers an unparalleled retreat, where every moment is infused with coastal charm and cherished memories await.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 8brbrBedroomsbrbr-Total 4brbr-1st Floor Bedroom: 1 Daybed w/ Trundle (2 Twins) and en suite Full Bathroombrbr-2nd Floor Bedroom: 1 King Bed (pass through to twins room)brbr-2nd Floor Bedroom: 1 Queen Bedbrbr-2nd Floor Bedroom: 2 Twin Beds (pass through from king bedroom)brbrBathroomsbrbr-Total 2brbr-1st Floor: Full Bathroom w/ Shower (en suite Daybed/Trundle Bedroom)brbr-2nd Floor: Full Bathroom w/ Tub and handheld shower headbrbrOther Amenitiesbrbr-Split AC Systembrbr-WiFibrbr-Smart TVbrbr-Washer/Dryerbrbr-Propane Grillbrbr-Outdoor Showerbrbr-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-C0481762240

4

Bed

2

Bath

8

Sleeps

$776.78

/ Nightly

Private Vacation Home

Private Retreat for Families Yet Near Everything in Orleans!

Orleans, Massachusetts, United States

As you eagerly turn down the white shell driveway you will see this backlot property and instantly fall in love with this acre plus secluded setting! A little further ahead our stately house with its wrap around decks and multiple sunrooms comes into view and you’ll realize the drive (and even bridge traffic) was worth it!brbrOur 3 bedroom, 2.5 bath features an open floor plan ideal for entertaining. The well-equipped, updated kitchen with a spectacular island and stainless steel appliances is open to the dining area and creates the perfect space for family and guests to gather. Off the dining area, the living room offers beautiful window views to the outside, plenty of seating, and a Smart TV. This living area opens up to a huge 3 season sunroom surrounded by a deck that wraps the entire first floor and overlooks the private grounds.brbrUpstairs you will find a the master bedroom equipped with a king size bed. Adjacent to the master, is a large office/sitting area. Also upstairs is a second bedroom with two twin beds, and a newly updated full bathroom. On the ground floor, is a very private third bedroom with a queen bed and an ensuite full bathroom. In addition, there is another screened in sunroom, which is perfect for enjoying the outdoors, without being outdoors! This sunroom leads out to the driveway in front and to a gas-lined outdoor firepit in the backyard, perfect for a night of Smores!brbrThe outdoor area off the kitchen has a gas-lined Weber Grill and outdoor shower. The indoor/outdoor entertaining space and serene secluded setting all work together to make this a very special property!brbrHead over to Nauset Beach for some sun and surf or to Skaket Beach on beautiful Cape Cod Bay and walk the flats at low tide. It is about a mile walk to watch the Orleans Firebirds play Summer Baseball or continue a half mile more to get to downtown Orleans with the Hot Chocolate Sparrow, Farmer’s Market, Cape Cod Bike Trail, and some of the best dining in all the Cape! brMore details at WeNeedAVacation plus additional pics!brSaturday to Saturday rental/Minimum 7 day rental!

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Sleeps

$1135.59

/ Nightly

Private Vacation Home

Nauset Heights - The Ocean At Your Doorstep! (2127)

Orleans, Massachusetts, United States

CA Classic Cape Cod Rustic Jewel! Enjoy the tranquility of this extraordinary location with private access to Nauset Beach and Nauset Inlet. Rambling ocean front cottage boasts casual and comfortable charm. Inside, the cottage is spacious and clean, the quintessential Cape Cod beach vacation experience. You are in a place that time has forgotten. The beach house is able to sleep 10 with five bedrooms and two full baths, one with a tub, one with a shower. There is a large kitchen, dining area, and living room. The dining area features a large round table with spectacular views of the Atlantic. A great place to enjoy meals together. The bedroom sleeping arrangements are unique. On the main level, there are two bedrooms - One has a queen bed while the other has sturdy built-in bunks along with a crib. On the upper level, there are 3 more bedrooms: one bedroom has two twins, another has a double (note that many of these beds are built-ins) while the fourth bedroom has two built-in bunks. Outside there are steps down to the inlet water. A walk over the sandbar out to the ocean waves beyond. Perfect for the person with sand in their shoes, enjoy all the great amenities this home has to offer! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own. Pets considered with pet cleaning fee.

Bed

Bath

Sleeps

$622.04

/ Nightly

Private Vacation Home

Spacious 5-Bedroom Retreat in the Heart of Orleans, MA

Orleans, Massachusetts, United States

The perfect location! Ten minute walk to Cape Cod Baseball...fifteen minute walk to Orleans center...five minute walk to bowling...extraordinary playground next door with fields and tennis courts...five minutes by car to the Bay beach, ten minutes to Nauset. This versatile home has five bedrooms and two and a half baths. The kitchen is modern, with a Viking range and granite counters including a large island, and open to a full dining room with sliders to the deck with a Weber grill. The five bedrooms will sleep as many as 10 people. The sitting area downstairs includes a 52 in Smart TV and a washer and dryer. There is also a second kitchen for snacks! The living room has an electric recliner and a 65 in Smart TV. Right outside the back door is a spacious outdoor shower. Plenty of parking for you and your guests. You won't find a more family friendly house! Lots of fun outdoors with provided tennis racquets, baseball/softball equipment, corn hole game, wiffleball and plastic racquet game with balls. One bicycle available to use too! Ac unit recently added to the lower level too! brbr**Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

5

Bed

2

Bath

10

Sleeps

$410.07

/ Nightly

Private Vacation Home

Game Room, Central AC, Dog Friendly!

Orleans, Massachusetts, United States

Summary:brbr15595 - Dune Crest: Game Room, Central AC, Dog Friendly!brbrbrbrThe Space:brbrWelcome to Dune Crest, a spacious Cape Cod getaway nestled in picture-perfect Orleans, MA—ideal for families and friends seeking comfort, relaxation, and coastal charm. brbrbrbrUnwind in this bright, airy, dog-friendly home featuring central air conditioning and plenty of space to spread out. The home offers four inviting bedrooms across two levels: three on the main floor—including a primary suite with a king bed and ensuite bath, plus two queen bedrooms—and a fun kids’ room on the lower level with four twin beds. With two additional full bathrooms, the home comfortably accommodates up to 10 guests.brbrbrbrThe open-concept living and dining areas are designed for easy gathering, complete with WiFi and a fully equipped kitchen perfect for group meals. Start your mornings around the modern kitchen island with fresh coffee, or step outside to enjoy your peaceful yard. After a day of exploring, relax on the sunny patio, fire up the grill for a cookout, or share laughs around the wood-burning fire pit under the stars.brbrbrbrWhen it’s time to explore, you’re just minutes from some of Cape Cod’s best beaches. Skaket Beach—famous for its warm waters and spectacular sunsets—is less than a 10-minute drive away. Stop by Nauset Farms for fresh sandwiches and local treats before heading to the shore. A short drive brings you to Orleans’ charming Main Street, where you’ll find boutique shops and local favorites like Sunbird and Hole in One for breakfast, Land Ho! for casual lunch, or La Bella Vita for Italian-inspired dining. Don’t miss a scoop (or two) from Hot Chocolate Sparrow or Ice Cream Café on warm summer evenings.brbrbrbrFor adventure, rent kayaks at Goose Hummock Shop, fish along Town Cove, bike the Cape Cod Rail Trail, or visit the Cape Cod Museum of Natural History—all just a quick trip from your home base.brbrbrbrBack at the house, keep the fun going in the dedicated game room, complete with a foosball table and Nintendo Switch. Wind down outside surrounded by classic Cape Cod natural beauty. Bring your group, your pup (pets welcome!), and settle into Dune Crest—where carefree beach days turn into cozy nights. Book your Orleans retreat today and start making memories at Dune Crest.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog) brbr-Sleeps 10brbrBedroomsbrbr-Total 4brbr-1st Floor Bedroom: 1 King Bed (Ensuite)brbr-1st Floor Bedroom: 1 Queen Bedbrbr-1st Floor Bedroom: 1 Queen Bedbrbr-Ground Floor: 2 Day Beds w/trundle (4 Twin Beds Total)brbrBathroomsbrbr-Total 3brbr-1st Floor: Full Bathroom, with Shower (Ensuite w/ King Bed)brbr-1st Floor: Full Bathroom, with Tub/Shower Combobrbr-Ground Floor: Full Bathroom, with ShowerbrbrOther Amenities brbr-Central A/C (1st Floor)brbr-Mini Split AC (Ground Floor)brbr-WiFibrbr-Smart TV brbr-Game Roombrbr-Foosball Tablebrbr-Streaming Servicebrbr-Washer/Dryerbrbr-Propane Grillbrbr-Wood Firepit brbr-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-C0442421152

Bed

Bath

Sleeps

$529.25

/ Nightly

Private Vacation Home

Short Kayak Ride to Nauset Beach

Orleans, Massachusetts, United States

Warm and inviting home just 2 minutes from Salt Water Landing at Mill Pond and Roberts Cove with water access to Nauset Beach. brbrThis wonderful one story Cape style home offers many updates including new deck, outdoor furniture, mattresses and sofas. There is an open kitchen, dining area and living room on one side of the home with a terrific family/sunroom on the other side. These areas will easily accommodate guests looking for a quiet reading area or a large and bright entertaining area.brbrThere are also two full bathrooms; one with a tub/shower and one with a shower. And there are three bedrooms; 2 with queen beds and one with 2 twin beds.brbrThe family room leads to a nice deck with umbrella, table and chairs, and gas grill. Also featured is an enclosed outdoor shower and a lovely, ample back yard for fun and games or just relax in the Adirondack chairs.brbrAmenities: Four Window Air Conditioners (1 in each bedroom and 1 in the living area), Dishwasher, Electric Stove, Washer and Dryer, Microwave, Drip Coffee Maker, Wireless Internet, 1 Television with Basic Cable, Iron and Ironing Board, and 4 Beach Chairs. Sheets and towels are not included.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: 6 PEOPLE TOTAL (adults and children)br* PARKING FOR 2 VEHICLESbr* SHEETS AND TOWELS ARE NOT INCLUDED, available to rent from local linen company, we are happy to provide informationbrbrbr****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover 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 rental!brbrAs a guest of Kinlin Grover, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!brbrbr***GUEST REVIEWS***brbrWe've stayed at the Mill Pond cottage (29 Mill Pond Road) a number of times and with different configurations of guests - as a couple on honeymoon; with our family; with a touring group of musicians. It worked perfectly for all of these configurations! We love the cozy, welcoming feel of the cottage - it always feels like home. It's a wonderful location - quiet neighborhood; easy distance to the water; and wonderful walk around the mill pond. The cottage has everything you could possibly need, and then some! We love breakfasting at the picnic table on the deck; playing board games/doing puzzles in the living room; or snuggling and watching TV in the TV room. Even with a big group (we've visited with a group of 7 adults) it doesn't feel crowded and there's space to hang out. We'll be back, we hope soon!br- Verity T. (repeat tenant) from Amherst, MAbrbrThis lovely cottage is like the song Old Cape Cod. It has all the convenience of home and the nostalgia and ambiance of a beach vacation home. The furnishings are comfortable, more than adequate and all you need for living as well as vacationing is available. A short walk to a quiet very private beach, as well as beautiful old and new beach homes in an exclusive neighborhood. You will love it, trust me, I've enjoyed this area for over sixty years.br- Val D. from Rancho Mirage, CAbrbrWe love this cottage, it has everything when staying on Cape Cod. We have stayed in other cottages but this has always been the perfect balance, we love the backyard and the wood chairs on the grass and patio table that the owner's constructed themselves. The cove has the perfect walking trails and clams to dig if you get a permit. The neighbors have always been welcoming as we take walks around the neighborhood. We love going to the cottage during the month of July beginning of August when all the restaurants and activities of the town are available.br- Wendy Z. from Laguna Niguel, CAbrbrOur family has rented this cottage for the last 10 years. The cottage is spacious, very comfortable with all the amenities needed for a vacation. There is also a nice and well maintained garden where you can eat outside and where we enjoyed numerous barbecues. We also love the fact we can walk to the water and that the house is only a very short drive to the stores in East Orleans. A very special place and friendly owners. We just love it and are eager every year to come back for our vacation.br- Christian A. from Paris, FrancebrbrThe Mill Pond House: My husband and I look forward to our annual visits there with great anticipation. The house is clean, comfortable and cozy and set in a quiet and pretty neighborhood affording both privacy and easy accessibility to beaches, woodland hikes, restaurants, shops and all the attractions of a classic Cape Cod retreat. The cottage itself has two living rooms with dining areas that allow separate activities to take place without interference. Can't wait to get there again!br- Galene K. from Norwalk, CT

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$696.24

/ Nightly

Private Vacation Home

Adorable updated Cape in East Orleans!

Orleans, Massachusetts, United States

Charming 3 bedroom Cape in East Orleans near Town Cove, Nauset Harbor and 2 miles from Nauset Beach. Brand new kitchen in 2025 with quartz countertops, Thermador appliances, Serena and Lily pendants and stools. Three bedrooms on one level with new furnishings and fresh paint throughout. Outdoor living on oversized deck, breezeway and outside shower.

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$720.75

/ Nightly

Private Vacation Home

Coveside: Town Cove Waterfront

Orleans, Massachusetts, United States

Overlooking Orleans Town Cove and with direct access to the water, this beautifully remodeled home is your perfect Cape Cod vacation retreat!brLight and bright, with beautiful hardwood floors and an open floor plan, the main level has a large, fully equipped kitchen with granite counters and breakfast bar open to the dining area. The living room offers comfortable seating and TV for hanging out after a day at the beach. Large picture windows provide sunlight and beautiful water views. Also on the main level is the queen bedroom, full bathroom, and laundry. The upper level has the second full bathroom and three bedrooms - a very large king bedroom, and two additional bedrooms each with two twin beds.brbrStep out the front door to expansive views of Town Cove as you grill dinner on the patio. The lawn between the house and the water is part of your vacation retreat and provides direct access down a pathway to the water. Bring your kayaks and paddleboards! Relax and dine overlooking the water or relax in the hammock with a great beach read. Outdoor shower to rinse off after a day at the beach! Beach Chairs, and sunshade.brThe Cottage Street Bakery, Ice Cream Cafe, Cooke's Seafood and Lost Dog Pub are just around the corner for sweet treats and delicious food. Two of Orleans' famous beaches, Skaket and Nauset, are just 7 and 10 minutes by car.

4

Bed

2

Bath

8

Sleeps

$710.06

/ Nightly

Private Vacation Home

Town Cove Coastal Chic

Orleans, Massachusetts, United States

Located right on the shore of beautiful Town Cove in Orleans. This updated home has 3 bedrooms 2 1/2 baths Nicely appointed foyer and living room with expansive saltwater views, leads you to the sunroom, deck and pathway to the water (conservation protected, can get overgrown depending on the time of year.) Games and books fill bookcases and a large flat screen TV sits ready to fill a rainy day if needed. The kitchen is clean and bright and has a dining area overlooking the water. Unwind in the enclosed porch or out on the deck as the sun sets over town center. There are 2 bedrooms on the first floor, each with 2 twins. The one facing the Cove even has it's own en-suite half bath. There is also a full bathroom with a shower on the first floor. Upstairs is a newly renovated primary suite with a king bed and private full bath. Views of the water abound from the large picture window. Outdoor shower for rinsing off after the beach. Gas grill for outdoor cooking. Central a/c to keep you cool. Washer and dryer is accessed from outdoor space off the kitchen. This property is perfect for the water sports lover in the family. Fish, clam, kayak, sail and more. brMA Registration: C0039432240

3

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2

Bath

6

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$436.66

/ Nightly

Private Vacation Home

Easy Walk to Scenic Kent's Point in Beautiful Orleans, MA - Pet Friendly!

Orleans, Massachusetts, United States

Summary:brbrPerfect for families - walk to Crystal Lake for a swim. Easy drive to bay and ocean beaches. Close to town for excellent restaurants, shops, and more!brbrbrbrThe Space:brbrWelcome to Salt River Retreat, a delightful family home tucked away in a coveted Orleans neighborhood. This charming getaway is perfectly positioned for outdoor enthusiasts. A short stroll leads you to Kent's Point, a breathtaking stretch of seaside conservation land overlooking The River, a sparkling saltwater estuary off Pleasant Bay. Dog lovers are welcome to bring their furry friends along to explore the sun-dappled trails. For those who prefer a refreshing dip, Crystal Lake, a pristine 38-acre freshwater lake, is also within walking distance, offering the perfect spot to cool off on a warm summer day.brbrbrbrStep inside and you'll be greeted by a stunning living room with soaring vaulted ceilings and exposed wooden beams, creating a warm and relaxing ambiance. Sink into the plush seating for a cozy movie night, or simply unwind with loved ones after a day of adventure. Just beyond, the spacious kitchen is a cook's delight, with modern stainless steel appliances, generous counter space for meal prep, and everything you need to whip up family favorites. The kitchen flows seamlessly into a bright and cheerful sunroom, where a dining table invites you to share meals together while enjoying views of the outdoors. Out back you'll discover a spacious deck, perfect for sunbathing. The expansive yard is ideal for kids and dogs to play freely while you unwind with a good book or an afternoon cocktail. Each bedroom is comfortable and thoughtfully appointed, offering a restful retreat after a day of exploring all the wonderful things Cape Cod has to offer.brbrbrbrSalt River Retreat is conveniently located just minutes from all that Orleans has to offer while still providing a peaceful and private escape. A quick 5-minute drive brings you to the heart of downtown Orleans, where you can explore an array of fantastic restaurants, charming boutiques, grocery stores, and more. Both Cape Cod Bay and Nauset Beach on the Atlantic Ocean are easily accessible, giving you the best of both worlds, calm waters for family-friendly swims and rolling waves for the surf lovers in your group. Whether you're exploring scenic trails, basking in the sun by the water, or simply relaxing in this inviting home, Salt River Retreat is the perfect place to make unforgettable memories in this picturesque seaside village. Book your stay today and experience the best of Cape Cod living!brbrbrbrLayout of Bedrooms & Bathrooms:brbrbrbrMain LevelbrbrBedroom #1 - King bedbrbrBedroom #2 - Twin trundle bed and twin bunk bedbrbrBedroom #3 - Pull out sofa bedbrbrbrbrBathroom #1 - Full bathroom with walk in showerbrbrBathroom #2 - Half bathroombrbrbrbr**Linens and bath towels are included.**brbr**This is a pet friendly home. If you plan to bring a dog along, please notify Nauset Rental so we may gather some information about your pet for our records.**brbrbrbrOther Things to Note:brbr-

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$219.34

/ Nightly

Private Vacation Home

Bike to Nauset Beach or Walk to Mill Pond!

Orleans, Massachusetts, United States

Summary:brbr15533 - Beach Cruiser: Bike to Nauset Beach or Walk to Mill Pond!brbrbrbrThe Space:brbrThis quaint cottage is located in a quiet neighborhood in desirable East Orleans and is a short walk to preservation land and a salt water bay worthy of kayaking. Bring your bikes for a fast 10-minute ride to Nauset Beach or your kayaks for unending exploration in Town Cove, Mill Pond and access all the way to the Atlantic Ocean. The cottage has plenty of space for a small family with three bedrooms, one and a half bathrooms, dining area, and cozy living room for TV watching and board games. The kitchen is on the smaller side, but sufficient for meal prep. Most importantly, you’ll have a large outdoor deck on which to enjoy beautiful summer evenings, as you grill up fresh seafood, juicy burgers or local produce from nearby Nauset Farms market. Mill Pond is only a 10-minute walk down a nature trail. Home Details: -Sleeps 6 br-Single Level (2 Stair Walk-Up) br-Bedroom #1: 1 Queen Bed br-Bedroom #2: 2 Twin Beds br-Bedroom #3: 1 Twin Bed w/ Trundle br-Mini-Split A/C Unit in Living Room br-Cable TV br-WiFi br-Washer/Dryer br-NO Pets (fines remitted) br-Charcoal Grill br-Outdoor Shower br-Sheets and Bath Towels Provided with Beds Made Upon Arrival br-Cleaned with Hospital Grade DisinfectantbrC0043162240brbrbrbrThe Neighborhood:brbrOceanside

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$399.77

/ Nightly

Private Vacation Home

Orleans Beach Retreat

Orleans, Massachusetts, United States

Spacious 2 bedroom home close to Nauset Beach! Central ac. Nice sized kitchen with eat in area. Living room off kitchen area has ample seating. Separate den has a large flat screen smart tv. Two bedrooms and the bath are at the other end of the house. One room has a full/double and the other has 2 twin beds. Bathroom has a tub/shower combination. Outside you will find a large deck set up for cooking and relaxing. Gas Grill. Outdoor dining table with umbrella, plus additional outdoor seating. Outdoor shower is there to enjoy after a day at the beach. Nice flat yard is perfect for outdoor activities. Clothes line for wet towels and bathing suits. Washer and Dryer are located in the basement with access via the outdoor bulkhead. Dogs are welcome with owner approval.

2

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1

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4

Sleeps

Vacation Home Rentals By Owner In Orleans, MA

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