Oysterville 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 $550 per night (USD)
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 ...
From $550 per night (USD)Expedia
- From $564 per night (USD)
VRBO
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 $564 per night (USD)VRBO
- From $625 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 $625 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Charming home in Osterville close to beach! Includes beach pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Conveniently located a short walk to the Village of Osterville, this home is situated in charming neighborhood close to ...
From $475 per night (USD)VRBO
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Expedia
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 PricingExpedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $1075 per night (USD)
VRBO
Artistically decorated \"Windmill\" House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home is just a few hundred feet from Nauticus Marina but so private inside and out. Walk to the marina for sunsets ...
From $1075 per night (USD)VRBO
- From $2495 per night (USD)
VRBO
Newly Renovated Home Within The Exclusive Oyster Harbors Community
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Amazing summer vacation awaits in this beautiful 4-bedroom Osterville home. Located, on almost an acre, on the private i ...
From $2495 per night (USD)VRBO
- From $929 per night (USD)
VRBO
Private beach. Seaside cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Michelle Sylvia rental collection home. Three bedroom carriage house on private oceanfront estate in Wianno section of O ...
From $929 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 $1492 per night (USD)
VRBO
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 $1492 per night (USD)VRBO
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VRBO
\"Little Neck\" Cottage just 3 minutes to Dowses Beach and downtown Osterville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In historic Osterville village and less than 2 miles to Dowses Beach and the center of town, this is the ideal Cape Cod ...
Click For PricingVRBO
- 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 $1021 per night (USD)
VRBO
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 $1021 per night (USD)VRBO
- From $3000 per night (USD)
VRBO
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 $3000 per night (USD)VRBO
- From $2333 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 $2333 per night (USD)VRBO
- From $1475 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 $1475 per night (USD)VRBO
- 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 $194 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 $194 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 $1480 per night (USD)
VRBO
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 $1480 per night (USD)VRBO
- From $1567 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 $1567 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Enjoy & Relax! Beach Pass, Fire Pit, Osterville, MA! Cape Cod⚓️- Sleeps 10!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Jun 29 – Aug 31, 2024 7-night minimum stay **No Pets** A convenient location in a charming neighborhood minutes away fr ...
From $525 per night (USD)VRBO
- From $567 per night (USD)
VRBO
Traditional Osterville Cape on Golf Course Near Beach\/Village with Beach Pass
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Traditional Osterville Cape Cod home located on the second fairway of Wianno Country Club. Enjoy all the town of Ostervi ...
From $567 per night (USD)VRBO
- From $475 per night (USD)
VRBO
An Osterville Gem!!Very close to town and beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Gorgeous, spacious, and fully appointed home in OSTERVILLE VILLAGE! 4 bedroom, 2.5 bathroom home with large eat-in kitch ...
From $475 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 $950 per night (USD)
VRBO
\"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 $950 per night (USD)VRBO
- From $5000 per night (USD)
VRBO
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 $5000 per night (USD)VRBO
- From $711 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 $711 per night (USD)VRBO
- From $308 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 $308 per night (USD)VRBO
- From $1300 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 $1300 per night (USD)VRBO
- 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
- Click For Pricing
VRBO
Historic Home in Downtown Osterville with Beach Pass
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Originally built as a whaling captain's home, the Captain Alexander Bacon house combines old world charm with modern liv ...
Click For PricingVRBO
- 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 $425 per night (USD)
VRBO
Spacious Osterville Cape Getaway, Close to Beaches and Village. Pass Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come escape on the Cape at Evans Oasis in Osterville. This unique style home sleeps 6 but can accommodate up to 8. Great ...
From $425 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 $3900 per night (USD)
VRBO
Wianno Ave Home With Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Just renovated 5 bedroom, 4.5 bath - plus a pool house with separate half bath! Charming, clean and updated Cape-style h ...
From $3900 per night (USD)VRBO
- From $680 per night (USD)
VRBO
Beautifully Renovated Townhome Steps from Osterville Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Walk or bike to the restaurants, shops and beaches of Osterville! This 2 bedroom, 1 bath home in an ideal location was j ...
From $680 per night (USD)VRBO
- From $792 per night (USD)
VRBO
Osterville - Spacious home 4 bedroom 3 bathroom in Wianno
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom 3 bathroom home is perfectly located between the center of town and Dowses beach. The home is laid out ni ...
From $792 per night (USD)VRBO
- Click For Pricing
Expedia
A magical pond home in Osterville!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this unique home on Micah's Pond in Osterville, Ma. Perfect for a family or 2 couples, this 2+1 bedroom, 3 1/ ...
Click For PricingExpedia
- From $671 per night (USD)
VRBO
Pristine Osterville Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
About this space This is a newly renovated cottage in Osterville’s “golden triangle.” It is approximately a half mile fr ...
From $671 per night (USD)VRBO
- 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
- Click For Pricing
Expedia
In town Osterville village location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located beautifully renovated cape home. It is a five minute walk to Osterv ...
Click For PricingExpedia
- Click For Pricing
VRBO
Well-Located in Osterville Close to beach and village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Exclusive Michelle Sylvia rental home. Charming three-bedroom home in Osterville with an open floor plan. First floor m ...
Click For PricingVRBO
- From $864 per night (USD)
VRBO
Charming Osterville Home with Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Charming, spacious and clean home - steps from Joshua's Pond and tucked behind the village, just over half a mile! The h ...
From $864 per night (USD)VRBO
- Click For Pricing
VRBO
Spacious Osterville Gem
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful Cape Style home located in the heart of Osterville! Walking distance to downtown and a short drive to the beac ...
Click For PricingVRBO
- Click For Pricing
VRBO
Spacious Cottage with English-Style Garden in Osterville Village, Cape Cod
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Elf Hill cottage offers two double bedrooms (one on the ground floor, the other upstairs), a third bedroom with two twin ...
Click For PricingVRBO
- 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
- Click For Pricing
VRBO
Oyster Harbors with a Pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 6
Luxury on the Cape. This professionally decorated home in the gated community of Oyster Harbors offers 5 bedrooms, gourm ...
Click For PricingVRBO
- Click For Pricing
VRBO
Osterville Oasis - Comfortable Home with Peaceful Garden
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom home nestled in a desirable and quiet neighborhood less than a mile from the village center and close to D ...
Click For PricingVRBO
- 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 $572 per night (USD)
VRBO
In the heart of Osterville and one mile to Dowses beach.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Exclusive Michelle Sylvia rental collection home. Less than a mile to the heart of Osterville and one mile to Dowses Be ...
From $572 per night (USD)VRBO
- From $1429 per night (USD)
VRBO
Heated pool, close to beach.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Michelle Sylvia high end collection. New for 2023! One of the most sought-after streets in all of Osterville. Heated poo ...
From $1429 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
- Click For Pricing
VRBO
Pristine Beach House with New Owners & Updates! Barnstable Beach Pass Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***This is a Saturday to Saturday Rental In Season*** Pristine family home privately situated on a corner lot in a quie ...
Click For PricingVRBO
- From $2089 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 $2089 per night (USD)VRBO
- From $766 per night (USD)
VRBO
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 $766 per night (USD)VRBO
- From $224 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 $224 per night (USD)Expedia
- From $608 per night (USD)
VRBO
Perfectly Located Osterville Rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This three bedroom, two and a half bath rental is located in the highly desirable Oyster Hills neighborhood of Ostervill ...
From $608 per night (USD)VRBO
- From $1600 per night (USD)
VRBO
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 $1600 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Osterville Village newly renovated one mile to beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful newly renovated contemporary cape with first floor master bedroom. Beautiful outdoor space with new mahogany d ...
From $411 per night (USD)VRBO
- From $425 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 $425 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
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Expedia
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 ...
Click For PricingExpedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $2250 per night (USD)
Expedia
Waterfront 4 beds in Oyster Harbors
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This architectural award winning home is on Oyster Harbors and overlooks our private marina. Walk a few hundred feet to ...
From $2250 per night (USD)Expedia
- Click For Pricing
VRBO
Antique elegance in Osterville
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Four large rooms on first floor…Master bedroom, Livingroom, kitchen/family room and glassed in porch. An adjacent outdo ...
Click For PricingVRBO
- From $286 per night (USD)
Expedia
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 $286 per night (USD)Expedia
- 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 $625 per night (USD)
Expedia
Your home away from home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home! Centrally located in sought after Osterville, MA, this 2 bed, 2 full bath home offe ...
From $625 per night (USD)Expedia
- From $539 per night (USD)
VRBO
Close to beautiful Dowses beach, central AC, and pet friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
4 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Saturday-to-Saturday rental reservation is required during peak summer weeks. ...
From $539 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Cape Oasis in sought after Osterville. Private pool, deck, hot-tub, 3bdrms.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! Centrally located in sought after Osterville, MA, this 3 bedroom, 2 full bath home ...
From $650 per night (USD)VRBO
- From $1071 per night (USD)
VRBO
Updated with Pool in Charming Osterville Village: 032-Ov
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
This property is professionally managed by Pretty Picky Properties. Updated with Pool in Charming Osterville Village N ...
From $1071 per night (USD)VRBO
- From $406 per night (USD)
Expedia
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 $406 per night (USD)Expedia
- From $337 per night (USD)
VRBO
Swing Set, Plunge pool, and large yard await!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 21012 - Oyster Circle: Swing Set, Plunge pool, and large yard await! The Space: Over the bridge to Osterville, ...
From $337 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 $3929 per night (USD)
VRBO
The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Michelle Sylvia high end Luxury collection rental home. Welcome to Osterville! This spacious newly renovated rental prop ...
From $3929 per night (USD)VRBO
- From $3572 per night (USD)
Expedia
NEW listing for 2024! Pool, dock, views and luxury living. In Oyster Harbors.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Michelle Sylvia high end collection. Discover the epitome of coastal elegance in the prestigious, gated enclave of Oyste ...
From $3572 per night (USD)Expedia
- Click For Pricing
VRBO
3 bedroom Osterville home, Beach Pass Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Centrally-located and well-maintained Osterville home with a large private yard, three full bedrooms, and upper-and-lowe ...
Click For PricingVRBO
- From $4214 per night (USD)
VRBO
New 2024 Osterville Seaside Estate - Luxury Retreat w\/ Heated Swimming Pool
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Osterville Seaside Estate, a bright white mansion with ocean views in a highly sought after village on Cape C ...
From $4214 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 $375 per night (USD)
VRBO
Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 7
Walk or bike to Osterville Village or the beach! Less than a half mile to the quaint village, where you'll find restaura ...
From $375 per night (USD)VRBO
- From $3572 per night (USD)
VRBO
Gated community luxury home in Oyster Harbors, Osterville.
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Michelle Sylvia luxury collection rental home. This rental home is a luxurious and well-appointed property located wit ...
From $3572 per night (USD)VRBO
- From $429 per night (USD)
VRBO
New for 2024! Close to Osterville village and Dowses beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Michelle Sylvia rental collection. Brand new for summer 2024! This charming Osterville rental home is ideally situated j ...
From $429 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 $1125 per night (USD)
VRBO
Exclusive Luxury Property On Gated Grand Island *POOL*
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 12
Relax in this masterpiece situated within the secure gated community of Grand Island! Partake in a spirited tennis matc ...
From $1125 per night (USD)VRBO
- From $2643 per night (USD)
VRBO
Sun Filled Modern Waterfront luxury rental home with dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Michelle Sylvia high end collection. Cape Cod waterfront home in Osterville. Magnificent sun-filled summer home with a ...
From $2643 per night (USD)VRBO
- From $1179 per night (USD)
VRBO
In the Heart of Osterville Village Newly renovated Pets considered
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Michelle Sylvia rental collection. LOCATION!!! In the Heart of Osterville Village. Walk to town, shopping, dining, bea ...
From $1179 per night (USD)VRBO
- From $342 per night (USD)
VRBO
Osterville~Newly Renovated with central AC and beach pass
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Osterville ~Total renovation recently completed and now available for the 2024 rental season. Minimum age to rent is 28. ...
From $342 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Enchanting 2 Bedroom Cottage - 1 block to Village Center
- 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 $350 per night (USD)VRBO
- From $895 per night (USD)
VRBO
Quaint Osterville home with Swim Spa, on 1+ acre, close to Dowse's beach
- 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 $895 per night (USD)VRBO
- From $567 per night (USD)
VRBO
Prime Osterville Location - Clean and Comfortable Family Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $567 per night (USD)VRBO
- From $1214 per night (USD)
VRBO
Large waterfront home with deep water dock, you'll Fall in love with Breezy Bluff
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Professionally managed by Kinlin Grover Vacation Rentals You're sure to fall in love with Breezy Bluff! This amazing 5 b ...
From $1214 per night (USD)VRBO
- From $1557 per night (USD)
VRBO
Beautiful 5* 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 brand new gunite 18 x 36 ft heated pool, is perfect fo ...
From $1557 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Osterville Gem - close to Beach \/ Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Picturesque, completely renovated 8 room seaside home is surrounded by stunning hydrangeas & roses. Just 1.5 blocks to O ...
From $900 per night (USD)VRBO
- From $872 per night (USD)
VRBO
Osterville Village - New Pool + Hot Tub! 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 $872 per night (USD)VRBO