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VRBO
Enjoy your own private beach with family and friends!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Fully appointed beautiful Cotuit Beach Front home with gourmet kitchen. Enjoy relaxing on your own private beach. Cook ...
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VRBO
From $368 per night (USD)
VRBO
Central air, FREE beach pass, Wifi, outdoor shower, deck and grill, quiet area!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Lovely grounds, two story home, one mile to private beach, many more beaches within short driving distance, large kitche ...
From $368 per night (USD)
VRBO
From $1921 per night (USD)
VRBO
Lovely Osterville Home With New Gunite Pool and Beach Pass.
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Newly renovated 3,000 sq ft Osterville home that boasts the detail of a traditional Cape as well as the luxury of a newl ...
From $1921 per night (USD)
VRBO
From $691 per night (USD)
Expedia
WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, Sleeps10!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Includes beach pass (savings of $175) *July and August are Saturday to Saturday rentals only. A convenient location in ...
From $691 per night (USD)
Expedia
$Traditional 4BD Cape on Wianno Golf Course. Walk to Village\/Marina w\/Beach Pass.$
From $765 per night (USD)
VRBO
Traditional 4BD Cape on Wianno Golf Course. Walk to Village\/Marina w\/Beach Pass.
Bedrooms:
2
Bathrooms:
6
Sleeps:
8
Traditional Osterville Cape Cod home located on the second fairway of Wianno Country Club. Enjoy all the town of Ostervi ...
From $765 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Charming Summer Cottage in beautiful historic village, walk to Beaches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Charming Cape Cod Retreat | Walk to Beach, Harbor & Historic Village Escape to this elegantly simple yet beautifully re ...
From $352 per night (USD)
Expedia
From $558 per night (USD)
VRBO
An Osterville Gem!!Very close to town and beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Gorgeous, spacious, and fully appointed home in OSTERVILLE VILLAGE! 4 bedroom, 2.5 bathroom home with large eat-in kitch ...
From $558 per night (USD)
VRBO
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Expedia
HOUSE IN BEAULTIFULL CAPE COD FOR RENT
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Fun for the whole family. 3 bedrooms 2 baths house with an open concept main level with ample outdoor space. 1 bedroom i ...
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Expedia
From $848 per night (USD)
VRBO
In the Heart of Osterville Village Newly renovated Pets considered RPMS087
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Michelle Sylvia rental collection. LOCATION!!! In the Heart of Osterville Village. Walk to town, shopping, dining, bea ...
From $848 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Great Osterville rental for families! Chef's kitchen and updated bathrooms. Short drive to beach, pond or charming Oster ...
From $402 per night (USD)
Expedia
$Beautiful Sea Captain's House walk to beach, central A\/C and outdoor shower$
From $916 per night (USD)
VRBO
Beautiful Sea Captain's House walk to beach, central A\/C and outdoor shower
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Beautifully updated Historic Sea Captain s House built for Captain Mazeppa Nickerson circa 1880. Enjoy old fashioned Cap ...
From $916 per night (USD)
VRBO
$Cape escape with patio, grill, firepit, outdoor dining, W\/D$
From $742 per night (USD)
Expedia
Cape escape with patio, grill, firepit, outdoor dining, W\/D
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Osterville Odyssey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $742 per night (USD)
Expedia
From $2799 per night (USD)
VRBO
Craigville Long Beach Beachfront rental home. Steps to private beach. RPMS029
Bedrooms:
5
Bathrooms:
4
Sleeps:
9
Michelle Sylvia Coastal Rental Collection New for 2025: A stunning patio and fire pit to make your beachside evenings un ...
From $2799 per night (USD)
VRBO
From $1294 per night (USD)
Expedia
Private Deep Water Dock, heated pool and hot tub. RPMS005
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Welcome to the Michelle Sylvia Coastal Collection, where luxury meets the natural beauty of Cape Cod. This stunning wate ...
From $1294 per night (USD)
Expedia
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VRBO
Cotuit Overlook
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Come celebrate 2023 at the small seaside town of Cotuit MA, "the overlook" of Ropes Beach. A quick 2 minute walk down th ...
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VRBO
From $401 per night (USD)
Expedia
Spacious Family Getaway. Barnstable Beach pass included
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Comfortable Family Home in a quiet Osterville neighborhood.Great for your Cape Cod summer vacation.Tastefully updated,of ...
From $401 per night (USD)
Expedia
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VRBO
Charming Cottage, Steps From Craigville Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Cape is now open for visitors. Plan your Cape Cod escape to this quintessential cottage, directly on the Centervill ...
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VRBO
From $1773 per night (USD)
Expedia
Overlooking Nantucket Sound, Classic Victorian Era home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Fabulous Waterview 5 bedroom and 3 1/2 bath home. Spacious rooms, abundant sunlight, HVAC,lots of space to spread out ...
From $1773 per night (USD)
Expedia
From $654 per night (USD)
VRBO
PRIVATE OASIS:4min CraigvilleBch-AC-FirePit-OutdoorShower-BeachPass-bikes-kayaks
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in our spacious home in the perfect central Cape Cod location! A short bike ride or 4 minute drive to Craigville ...
From $654 per night (USD)
VRBO
From $1313 per night (USD)
Expedia
Large 7 bedroom, 5 bath house one and a half blocks from the beach
Bedrooms:
5
Bathrooms:
7
Sleeps:
24
Welcome to The Grey Whale, a spectacular vacation rental nestled in the charming seaside village of Cotuit, less than a ...
From $1313 per night (USD)
Expedia
From $609 per night (USD)
VRBO
CAPE ESCAPE !!! NEW LISTING
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
CAPE ESCAPE !!! Fully Renovated Located in the heart of Cape Cod , this newly renovated house , can offer you everything ...
From $609 per night (USD)
VRBO
From $648 per night (USD)
Expedia
Magnificent Ocean Views, Just Steps to Craigville Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Directly across from the Beach. Swim in the warm waters of Nantucket Sound just steps from our front door. This 5 bedro ...
From $648 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Perfect Vacation Getaway!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy Cape life in this sunny, spacious all seasons home 3-5 minutes from picturesque beaches and charming Osterville vi ...
From $249 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Location, Location --beachfront property overlooking Cotuit Harbor.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This immaculate waterfront cottage is located in the village of Cotuit overlooking Cotuit Harbor. Cotuit is located app ...
From $330 per night (USD)
Expedia
From $347 per night (USD)
VRBO
THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Quiet three bedroom, two full bath Cape located on a dead-end street in the quaint town of Osterville. First floor inclu ...
From $347 per night (USD)
VRBO
$Osterville Gem with Central A\/C and Walking Distance to Joshua’s Pond!$
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Expedia
Osterville Gem with Central A\/C and Walking Distance to Joshua’s Pond!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful home is located within walking distance of Osterville Village and Joshua's Pond and a few minutes drive t ...
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Expedia
From $748 per night (USD)
VRBO
Charming, Historic Farmhouse with private pool on quiet street, beach pass
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming, historic ( George L. Hamblin House) 4 bedroom, 2 1/2 bath farmhouse nestled on 2 acres on a quiet, wooded stre ...
From $748 per night (USD)
VRBO
From $1469 per night (USD)
Expedia
Luxurious farm house colonial with pool & amenities near beach. Sleeps 20.
Bedrooms:
5
Bathrooms:
7
Sleeps:
20
An unbelievable setting in one of Cape Cod's finest luxury residences. Situated on nearly two acres, packed with ameniti ...
From $1469 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Peaceful Guest House Cottage, w air conditioning and only 0.2 to private beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A spacious, one room studio, steps away from Oregon Beach. Located at the end of Main Street, with access to all that C ...
From $363 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Contemporary Gem with Private Pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 21001 - Splash Landing: Contemporary Gem with Private Pool! The Space: Take time to slow down and relax poolsi ...
From $601 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Osterville~Newly Renovated with central AC and beach pass
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Osterville ~Total renovation recently completed and now available for the 2024-2025 rental season. Minimum age to rent i ...
From $415 per night (USD)
VRBO
$COTUIT RETREAT! BEAUTIFUL 3 BR\/CENTRAL AC$
From $425 per night (USD)
Expedia
COTUIT RETREAT! BEAUTIFUL 3 BR\/CENTRAL AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful fully renovated home located in a lovely neighborhood in Cotuit! Neighborhood side walked for easy walking, ru ...
From $425 per night (USD)
Expedia
From $1419 per night (USD)
VRBO
Beautiful designed, newly constructed home- all the amenities, close to beaches
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
This beautiful, spacious newly constructed home is situated on a 1/2 acre lot located on Little Island, Osterville, clos ...
From $1419 per night (USD)
VRBO
$\The Half Shell\ Cottage in Osterville Village$
From $1246 per night (USD)
Expedia
\"The Half Shell\" Cottage in Osterville Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
In the heart of historic Osterville village and about a mile to Dowses Beach this is the ideal Cape Cod central Air Cond ...
From $1246 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Charming Ranch on the Cape
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This is a cozy little ranch centrally located on the cape. The place features a huge front and back yard. Would be great ...
From $455 per night (USD)
VRBO
From $5522 per night (USD)
Expedia
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Brand new construction on Sea View Ave in Osterville. This little oasis boasts a pool, hottub, and tennis court. The hom ...
From $5522 per night (USD)
Expedia
From $2472 per night (USD)
VRBO
Private Nantucket style home with heated pool and beach pass
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Immaculate 3,500 sq ft 4 bedroom, 4 bath Osterville home that boasts the ambience of Cape Cod while providing a luxury s ...
From $2472 per night (USD)
VRBO
From $814 per night (USD)
Expedia
Lovely family home in the heart of historic Cotuit. Beach pass included.
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Celebrating 10 years of excellence, this is one of Barnstable’s longest continuously rented owner-managed homes—an elega ...
From $814 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
Exclusive Little Neck Island Cape Cod House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Best town on the Cape, Osterville! High cathedral ceilings in queen bedroom and king master bedroom. Newly renovated, ...
From $1030 per night (USD)
VRBO
$Contemporary Home w\/ Private Hot Tub, Deck, Game Room & Shared Dock Access$
From $1045 per night (USD)
Expedia
Contemporary Home w\/ Private Hot Tub, Deck, Game Room & Shared Dock Access
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Bumps River Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $1045 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Enchanting 2 Bedroom Cottage - 1 block to Village Center-BEACH PASS-Weekly only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Completely renovated 2 Bedroom, 1.5 Bath Duplex just one block to Osterville Village. Living Room with vaulted ceilings, ...
From $486 per night (USD)
VRBO
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Expedia
Welcoming home on Main St. with screened porch & large yard - 1 dog OK
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Wendell K Backus House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
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Expedia
$Waterfront\/golf Sleep 8 \/public beach Pass & private beach$
From $1550 per night (USD)
VRBO
Waterfront\/golf Sleep 8 \/public beach Pass & private beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Rare Nature Lovers Waterfront compound on an unspoiled fresh spring fed pond. Located in the exclusive Wianno section, l ...
From $1550 per night (USD)
VRBO
From $705 per night (USD)
Expedia
Cape House Retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Perfect entertaining house year round! Fire pit, hot tub, pool/ping pong table, board games, books, beach gear, fire pla ...
From $705 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Charming Cottage at Craigville Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up with a lovely view and just steps away from popular Craigville Beach. Clean, charming and newly updated 2 bedroo ...
From $538 per night (USD)
VRBO
From $895 per night (USD)
Expedia
Pristine, carefully restored, 1700s farmhouse, inground pool, private 3 acres
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
**New to rental market as of January 2019** Welcome to the William Marston House circa 1780, located conveniently in the ...
From $895 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
Craigville Beach Home ~ Create Memories to Last a Lifetime!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
We welcome you to share our lovely bright 2 story home, steps from Craigville Beach in Centerville on Cape Cod, MA with ...
From $1030 per night (USD)
VRBO
From $760 per night (USD)
VRBO
4 Bed Osterville Home with Yard
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Stay at this recently renovated 4 bed 3.5 bath Osterville home. Less than a 5 minute walk to Joshua pond ,1 mile from Do ...
From $760 per night (USD)
VRBO
From $780 per night (USD)
VRBO
Osterville Cape Cod-Style Home - One Block from North Bay!
Bedrooms:
6
Bathrooms:
6
Sleeps:
10
Osterville on Cape Cod. Pleasant Cape Cod-style home one block from North Bay just off Bay Street. Walk to village and s ...
From $780 per night (USD)
VRBO
From $578 per night (USD)
Expedia
Spacious Osterville home, short commute from Boston, <mile to Beach and Village.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come escape on the Cape to Osterville - quaint Cape Town less than 20 miles over the bridges. This ranch style home slee ...
From $578 per night (USD)
Expedia
$Brand New Osterville Home! Central AC, Walk\/Bike to town or beach, Sleeps 10$
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VRBO
Brand New Osterville Home! Central AC, Walk\/Bike to town or beach, Sleeps 10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Located minutes from Main Street Osterville and Dowses Beach, this house is the perfect location. The first floor has a ...
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VRBO
From $553 per night (USD)
Expedia
Adorable Pond Front Home Walking Distance to Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pond-front living in the center of charming Osterville village! This two bedroom, one bath home sits on Sam's Pond in Os ...
From $553 per night (USD)
Expedia
$Charming & Bright Beach House • Walk to Craigville Beach • AC \/ strong wifi$
From $929 per night (USD)
VRBO
Charming & Bright Beach House • Walk to Craigville Beach • AC \/ strong wifi
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
𝐂𝐚𝐩𝐞 𝐂𝐨𝐝 𝐂𝐡𝐚𝐫𝐦 𝐌𝐞𝐞𝐭𝐬 𝐂𝐨𝐚𝐬𝐭𝐚𝐥 𝐋𝐮𝐱𝐮𝐫𝐲: 𝐘𝐨𝐮𝐫 𝐃𝐫𝐞𝐚𝐦 𝐁𝐞𝐚𝐜𝐡 𝐄𝐬𝐜𝐚𝐩𝐞 𝐀𝐰𝐚𝐢� ...
From $929 per night (USD)
VRBO
From $1817 per night (USD)
Expedia
Luxury, Waterfront, Beach, AC, Heated Pool, Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
4 bedrooms- 4 Bathrooms- Sleeps 8 It is a required to book a minimum of 5-7 nights during peak summer weeks, Friday arri ...
From $1817 per night (USD)
Expedia
$Spectacular waterfront home \/ boat dock Indoor & Outdoor pool$
From $3147 per night (USD)
VRBO
Spectacular waterfront home \/ boat dock Indoor & Outdoor pool
Bedrooms:
8
Bathrooms:
7
Sleeps:
10
Overlooking the sparkling waters of Prince Cove this Contemporary waterfront property with Deep Water Dock provides easy ...
From $3147 per night (USD)
VRBO
From $1164 per night (USD)
Expedia
Quaint Osterville home with Swim Spa
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This newly renovated, quaint 1600 square feet Osterville home is a peaceful retreat for families. It is located in an up ...
From $1164 per night (USD)
Expedia
Click For Pricing
VRBO
Walk to village and beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Modern Cape with backyard oasis. Walk to Dowse’s beach and Osterville village and then retreat to your private pool. Ren ...
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VRBO
From $3405 per night (USD)
Expedia
Expansive Cape Cod Family Retreat
Bedrooms:
7
Bathrooms:
11
Sleeps:
22
A spacious and welcoming home in a wonderful location. This home allows plenty of room for multi families to vacation to ...
From $3405 per night (USD)
Expedia
From $1972 per night (USD)
VRBO
Impressive Osterville Residence - Ideal Location
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
Originally built in 1886, this home has been a well-loved Wianno area summer home for well over a century. Its proximit ...
From $1972 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 Bedroom - 2 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $412 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Newly renovated Cottage Across the street from Craigville Beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly Renovated One Bedroom Cottage with Living Room, full kitchen, and bathroom. It is approximately 600 sf. I have re ...
From $352 per night (USD)
VRBO
$FULL WINTER RENTAL: NOV. 1, 24---MAY 31, 25\n2195. PER MONTH PLUS UTILITIES. \n$
From $460 per night (USD)
Expedia
FULL WINTER RENTAL: NOV. 1, 24---MAY 31, 25\n2195. PER MONTH PLUS UTILITIES. \n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy the best of Cape Cod from this Nantucket style Cottage just steps to Craigville Beach- 3 bedrooms, 2 full baths, u ...
From $460 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Falling Leaf Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $240 per night (USD)
VRBO
From $738 per night (USD)
Expedia
Salt Box Minutes to Beaches & Golf Courses
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcoming Cotuit home with a wrap around deck, private back yard, central air and ample space for you and your friends & ...
From $738 per night (USD)
Expedia
From $1463 per night (USD)
VRBO
Heated Private Pool, Walk to beach & shops, fully renovated house
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
A five minute walk to Osterville's Wianno Club on Seaview Ave and to Dowse's Beach, this four bedroom, four bath home w ...
From $1463 per night (USD)
VRBO
From $806 per night (USD)
Expedia
Beautiful Osterville Home central to everything!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful 3 bed, 2 1/2 bath cape is centrally located close to everything! It is right on the Wianno Golf Course, ...
From $806 per night (USD)
Expedia
From $867 per night (USD)
VRBO
Prime Osterville Location - Clean and Comfortable Family Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
An enjoyable stroll from Dowses Beach or to the village center, this home offers plenty of space for your family to enjo ...
From $867 per night (USD)
VRBO
From $1750 per night (USD)
Expedia
Center Of It All: 454-Cv Sea Captain's Estate with Heated Pool and Pickle Ball Court
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
This property is professionally managed by Pretty Picky Properties. Sea Captain's Estate with Heated Pool and Pickle Ba ...
From $1750 per night (USD)
Expedia
From $930 per night (USD)
VRBO
Waterfront • Pet Friendly • Book NOW for 2025
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
IMMACULATE -- we meet or exceed all cleaning and disinfecting protocols at this location. Our cleaning staff has been sp ...
From $930 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Charming Cottage, breezy, bright and peaceful. Walking distance to beach and bar
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Our well cared for Cape house is located in Barnstable's Village of Cotuit. The house is situated on Lewis Pond (kayaks ...
From $315 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Charming home in Osterville close to beach! Includes beach pass
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Conveniently located a short walk to the Village of Osterville, this home is situated in charming neighborhood close to ...
From $535 per night (USD)
VRBO
From $1337 per night (USD)
Expedia
Charming Carriage House on Private Oceanfront Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three bedroom carriage house on private oceanfront estate in the Wianno section of Osterville. Originally built as stab ...
From $1337 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Cape-style home in private neighborhood
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Bright, beachy decor and an open floor plan greet you in this centrally located Cape home with countless amenities. Loc ...
Click For Pricing
VRBO
From $2175 per night (USD)
Expedia
Beautifully Renovated Cape Cottage with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Set in a lovely neighborhood by the beach, this 3 bedroom Osterville cottage is the perfect home to make family memories ...
From $2175 per night (USD)
Expedia
From $727 per night (USD)
VRBO
Private escape on Cape Cod
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The Perfect vacation house!!! Huge deck for outdoor entartement,private seating on over of acre land in the heart of C ...
From $727 per night (USD)
VRBO
From $437 per night (USD)
Expedia
A Cotuit Escape- located on Main Street steps from Kettleer baseball park
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming property sits on .8 acres near Lowell Park, home of the Cotuit Kettleers baseball team. The huge back yar ...
From $437 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Craigville Beach at your doorstep!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the perfect vacation location YEAR ROUND or weekly in season or off season! Just 4 cottages from Craigville Beach ...
From $513 per night (USD)
VRBO
From $1066 per night (USD)
Expedia
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
The perfect setting for enjoying summertime in Osterville. This comfortable three bedroom home is overflowing with charm ...
From $1066 per night (USD)
Expedia
Click For Pricing
VRBO
Comfortable holiday home in Cotuit
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
We are delighted to share our beloved family vacation home with you! Four bedrooms and 3 baths provide plenty of space. ...
Click For Pricing
VRBO
From $337 per night (USD)
Expedia
Great Outdoor Space Central AC WIFI Family Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
3 Bedroom - 1.5 Baths - Sleeps 5 During Peak Summer Season Until Labor Day - a 7-night Friday-to-Friday rental reservati ...
From $337 per night (USD)
Expedia
$Serene Haven w\/ No Shared Spaces | Cape Cod$
From $262 per night (USD)
VRBO
Serene Haven w\/ No Shared Spaces | Cape Cod
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
My peaceful 2-bedrooms, 1 bathroom residential private apartment (Entire Main Level) has everything you need for your Ma ...
From $262 per night (USD)
VRBO
From $2183 per night (USD)
Expedia
Cotuit Home with an Inground Pool less One Block from the Beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Guests are sure to enjoy a memorable vacation in this fully furnished single family on a cul de sac, 6 bedroom/4 full ba ...
From $2183 per night (USD)
Expedia
$New construction! Craigville Beach, Main St, Playground, Ice cream\/restaurants!!$
From $705 per night (USD)
VRBO
New construction! Craigville Beach, Main St, Playground, Ice cream\/restaurants!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
New construction. A beautiful 4 bedrooms 2 & 1/2 baths +an outdoor shower. Quarts countertop & hardwood floor througho ...
From $705 per night (USD)
VRBO
From $1020 per night (USD)
Expedia
BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This very large beautiful home in Osterville has everything you need for a fantastic vacation! The home was built in 200 ...
From $1020 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Charming Cottage Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Our quaint cottage is located just a minute's walk from Osterville's village center, with its upscale shopping, dining a ...
From $345 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Winter, Spring, Summer, Fall, this Cape close to the beach has it all!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come enjoy your Cape Cod vacation in Cotuit with easy access on and off the Cape by staying in a quintessential Cape hou ...
From $529 per night (USD)
Expedia
From $1511 per night (USD)
VRBO
Large waterfront home with deep water dock, you'll Fall in love with Breezy Bluff
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Professionally managed by Kinlin Grover Vacation Rentals You're sure to fall in love with Breezy Bluff! This amazing 5 b ...
From $1511 per night (USD)
VRBO
From $1717 per night (USD)
Expedia
Amazing updated waterfront home located in Osterville with a private dock, elevator and AC.
Bedrooms:
1
Bathrooms:
1
Sleeps:
12
Professionally managed by Kinlin Grover Vacation Rentals Step back in time to this amazing 7 bedroom 5 and half bath cla ...
From $1717 per night (USD)
Expedia
From $1087 per night (USD)
VRBO
Beautiful 5 Star Home. Sleeps 13. Heated pool, bike to beach & quaint village
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Beautifully presented summer home on an acre of land, featuring a gunite 18 x 36 ft heated pool, is perfect for family g ...
From $1087 per night (USD)
VRBO
From $921 per night (USD)
Expedia
Bright Marstons Mills Studio - Near Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perfect for couples or solo travelers, Marstons Mills studio provides a cozy Cape Cod atmosphere that makes everyone fee ...
From $921 per night (USD)
Expedia
From $2092 per night (USD)
VRBO
Unbeatable location, views and water access from this rare family compound
Bedrooms:
8
Bathrooms:
8
Sleeps:
20
Anchor to Windward has 8 bedrooms and 7.5 baths: a main house with 5 bedrooms and 5.5 baths and a boathouse directly on ...
From $2092 per night (USD)
VRBO
From $1118 per night (USD)
Expedia
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
Bedrooms:
6
Bathrooms:
4
Sleeps:
9
Welcome to Wianno House! Renovated top-to-bottom in 2022, this home is the perfect for vacationers seeking luxury accomm ...
From $1118 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Cotuit 5 bedroom, 3 bath home, pet friendly, great location! Will sleep up to 10+, Beach pass included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Kinlin Grover Compass Vacation Rentals This 4 bedroom 2 bath pet friendly home is located in the heart of Cotuit in a qu ...
From $449 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Historic Home in Prime Osterville Village Location: Three bedrooms, Sleeps 6
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Main Street House - combining history, luxury and location for the perfect Cape Cod vacation home. Main Stre ...
From $536 per night (USD)
Expedia
From $4510 per night (USD)
VRBO
Luxury home with 2 pools on the water. RPMS081
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Michelle Sylvia high-end collection rental home. NEW for 2025, indoor hot tub. Overlooking the sparkling waters of Pr ...
From $4510 per night (USD)
VRBO
From $1372 per night (USD)
Expedia
Private, Immaculate Home in Resort-Like Setting with Pool
Bedrooms:
6
Bathrooms:
4
Sleeps:
9
This beautiful vacation home with a heated gunite swimming pool, is set on over an acre of landscaped grounds and is loc ...
From $1372 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Perfectly Located Osterville Heights Rental RPAM021
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sun, sand and showers (outdoor that is!) await you at this perfectly situated 3 bed / 2 bath vacation rental in Ostervil ...
From $355 per night (USD)
VRBO
From $2304 per night (USD)
Expedia
4BR 4BA Osterville home with pool, hot tub, game room-minutes from the beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Starboard Retreat! With its expansive backyard oasis and close proximity to Craigville and Dowses Beaches, th ...
From $2304 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Spacious Stone Fire Pit Game Room!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: 21009 - Perfect Peach: Spacious Stone Fire Pit Game Room! The Space: Marston’s Mills is one of the many Barnst ...
From $451 per night (USD)
VRBO
From $836 per night (USD)
Expedia
Prime Centerville Location. One mile to Craigville beach RPMS044
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Michelle Sylvia rental collection. An inviting farmers porch welcomes you into this beautifully renovated 4-bedroom 3 ...
From $836 per night (USD)
Expedia

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Results: 174 Rentals