Prince Cove Rentals
- From $265 per night (USD)
VRBO
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Great Osterville rental for families! Brand new chef's kitchen and bathrooms. Short drive to beach, pond or charming Ost ...
From $265 per night (USD)VRBO
- From $564 per night (USD)
Expedia
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 $564 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- From $3400 per night (USD)
Expedia
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 $3400 per night (USD)Expedia
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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 PricingVRBO
- From $251 per night (USD)
Expedia
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 $251 per night (USD)Expedia
- From $760 per night (USD)
VRBO
BEAUTIFUL OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This very large beautiful New home in Osterville has everything you need for a fantastic vacation! The home was built in ...
From $760 per night (USD)VRBO
- From $538 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 $538 per night (USD)Expedia
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Expedia
Well-appointed home with gym, enclosed yard, private sauna, pool & game room
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Mystic Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingExpedia
- From $1214 per night (USD)
Expedia
Heated Pool.Jacuzzi.Game Rm.Playground@Green Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Green Haven is conveniently within easy access to supermarkets, pharmacy, coffee shops, restaurants, hardware store, and ...
From $1214 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Family Friendly Cape House Retreat with Beach Pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
Escape to the Cape and enjoy a family vacation in a spacious home just 2 miles from the beach yet centrally located on C ...
From $499 per night (USD)VRBO
- From $506 per night (USD)
VRBO
Spacious Tucked Away Home, 1.5m from Town
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy our open-floor planned home located just 1.5 miles from downtown Osterville. Explore the many shops, restaurants, ...
From $506 per night (USD)VRBO
- From $1134 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 $1134 per night (USD)VRBO
- From $285 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 $285 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Egyptian linens & Luxury amenities by Hermès, Lanvin & Molton Brown collections.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 92
It has many of the essentials and services that you would not expect to find in any of the vacation homes in town, such ...
From $1400 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Private Nantucket style home with heated pool and beach pass
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $700 per night (USD)VRBO
- From $620 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 $620 per night (USD)VRBO
- From $289 per night (USD)
VRBO
271 Westwind Cir - Charming, Pet-Friendly 3BR retreat, beach pass, AC, game room
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedrooms, Sleeps 6 3 Bathrooms 7-night minimum rental, Saturday - Saturday About this home: Discover the charm of 27 ...
From $289 per night (USD)VRBO
- From $695 per night (USD)
VRBO
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 $695 per night (USD)VRBO
- Click For Pricing
VRBO
Renovated Getaway: A\/C, Tennis, Private beach on North Bay. Close to everything
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You couldn’t have planned it better! Private beach on North Bay (0.8 miles), hiking around Eagle pond, tennis, grocery ...
Click For PricingVRBO
- From $650 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 $650 per night (USD)VRBO
- From $571 per night (USD)
Expedia
Osterville Cape Cod-Style Home - One Block from North Bay!
- Bedrooms:
- 6
- Bathrooms:
- 5
- 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 $571 per night (USD)Expedia
- From $250 per night (USD)
VRBO
A wonderful place with A wonderful beach to spend a vacation !!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful home in desirable Osterville Woods. Enjoy this charming 2 bedroom, 2.5 bath home with a spacious open living r ...
From $250 per night (USD)VRBO
- From $593 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 $593 per night (USD)VRBO
- From $330 per night (USD)
VRBO
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 $330 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Osterville Charmer in a private neighborhood setting
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Primrose Cottage, a perfect getaway or seasonal rental. This beautiful, custom designed Cape Cod style home ...
From $250 per night (USD)VRBO
- From $289 per night (USD)
VRBO
HUGE AUGUST DISCOUNT, 2023 only. Central air, FREE beach pass, Wifi, paradise!
- 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 $289 per night (USD)VRBO
- From $1557 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 $1557 per night (USD)VRBO
- Click For Pricing
VRBO
Cozy home, walking distance to Hamblin Pond Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect, spacious home in Marstons Mills for a family or multiple families recently renovated with lots of natural light ...
Click For PricingVRBO
- From $3901 per night (USD)
VRBO
Expansive Cape Cod Luxury estate w/heated pool, gym, firepit- 6 bedrooms, 8 bath
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 8
New Listing! Entire place for you and guests! The Beach Awaits! 6 Bedrooms, 7 beds, 8 Baths, plus outdoor shower, priv ...
From $3901 per night (USD)VRBO
- From $272 per night (USD)
VRBO
Charming cottage steps to Osterville village. Near Dowses beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Michelle Sylvia rental collection home. This is the most charming and updated cottage in the "village" that you will fi ...
From $272 per night (USD)VRBO
- From $272 per night (USD)
Expedia
Walk to Joshua Pond Beach & Downtown!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 21008 - Sun-Kissed Shores: Walk to Joshua Pond Beach & Downtown! The Space: The feeling of a Cape Cod summer d ...
From $272 per night (USD)Expedia
- From $219 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 $219 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Cheerful 3 Bedroom Home in Osterville - Great Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Updated, clean and airy 3 bedroom in Osterville. Beautiful and open living area with eat-in kitchen, stainless steel app ...
From $340 per night (USD)VRBO
- From $361 per night (USD)
VRBO
Beautiful spacious Cape Cod house with a large and private yard near beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious Cape Cod ranch house situated on a dead end street. The house can accomodate 8 people or more with th ...
From $361 per night (USD)VRBO
- From $1071 per night (USD)
Expedia
Seasons by the Sea: Fully Renovated Luxury Cape Cod Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Seasons by the Sea! Our fully remodeled Cape Cod has 4 bedrooms, 3.5 baths and all the outdoor living spaces ...
From $1071 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Falling Leaf Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $264 per night (USD)VRBO
- Click For Pricing
Expedia
Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy this charming cottage in a beautiful Cape Cod setting. The central location makes it within easy reach of all ...
Click For PricingExpedia
- Click For Pricing
Expedia
Charming East Coast oasis with private saltwater pool, large deck & grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Ocean Timberland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingExpedia
- Click For Pricing
Expedia
HOUSE IN BEAULTIFULL CAPE COD FOR RENT
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 ...
Click For PricingExpedia
- From $288 per night (USD)
VRBO
Cape escape with patio, grill, firepit, outdoor dining, fireplace & 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 $288 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Blossom Beach Cottage is a peaceful retreat in the heart of Osterville Village. Walking distance to Shopping, Dining, Po ...
From $399 per night (USD)VRBO
- From $399 per night (USD)
VRBO
4BR Ocean Timberland - Osterville w\/ private pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
" Ocean Timberland - Osterville Home w/ Private Pool, fire pit and spacious backyard” - Family Beach Vacation Retreat - ...
From $399 per night (USD)VRBO
- From $2286 per night (USD)
Expedia
NEW for 2024 ! Osterville pool rental near beach 32 day stay for August only
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Michelle Sylvia high end collection. Introducing the epitome of summer fun in the sun living: Newly unveiled for 2024 in ...
From $2286 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Spring, Summer & Fall Rentals located in beautiful Osterville MA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located 1 minute off of Route 28, right in between Falmouth and Hyannis. Want a little bit more action? Main Street, Hy ...
From $340 per night (USD)VRBO
- From $367 per night (USD)
VRBO
Pet Friendly Cozy Cotuit Cottage 5 minutes away from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Charming Cotuit cottage, located just minutes from the heart of town. This cozy home is perfect for a getaway to reset a ...
From $367 per night (USD)VRBO
- From $950 per night (USD)
VRBO
Newly renovated Barnstable house\/Pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your cape getaway at this family-friendly home, close to Craigsville beach, Loop Beach, and Sandy Neck beach. Larg ...
From $950 per night (USD)VRBO
- From $3572 per night (USD)
VRBO
Luxury Oyster Harbors Retreat With World Class Amenities
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 71 Sand Point. A truly luxurious 5 bedroom, 4.5 bathroom vacation rental property located on the private isl ...
From $3572 per night (USD)VRBO
- From $667 per night (USD)
VRBO
Monthly Osterville Village Luxury Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Osterville Village on Cape Cod is considered by many to be one of the premier summer resort destinations in New England. ...
From $667 per night (USD)VRBO
- From $929 per night (USD)
VRBO
Private Deep Water Dock, heated pool and hot tub.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Michelle Sylvia rental collection home. This beautiful Cape Cod home located in the village of Marston's Mills overlook ...
From $929 per night (USD)VRBO
- From $1529 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 $1529 per night (USD)VRBO
- From $626 per night (USD)
VRBO
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 $626 per night (USD)VRBO
- From $4000 per night (USD)
VRBO
Luxury home with 2 pools, [ indoor and outdoor ] dock, hot tub and more!
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Michelle Sylvia high-end collection rental home. Overlooking the sparkling waters of Prince Cove this Contemporary water ...
From $4000 per night (USD)VRBO
- From $208 per night (USD)
VRBO
Perfectly Located Osterville Heights Rental
- 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 $208 per night (USD)VRBO