Oysterville, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Oysterville, Massachusetts on RentalSaver.com!

Oysterville Rentals

Filter

Popular Areas

From $2112 per night (USD)
VRBO
Lovely Osterville Home With New Gunite Pool and Beach Pass.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
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 $2112 per night (USD)
VRBO
From $781 per night (USD)
Expedia
Fun & Sun in Osterville MA - Sleeps 10, Beach Pass
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Includes beach pass (savings of $175) A convenient location in charming neighborhood minutes away from Craigville Beach ...
From $781 per night (USD)
Expedia
From $920 per night (USD)
VRBO
Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Traditional Osterville Cape Cod home located on the second fairway of Wianno Country Club for nice breezes and quiet. En ...
From $920 per night (USD)
VRBO
From $697 per night (USD)
VRBO
An Osterville Gem!!Very close to town and beach!
Bedrooms:
2
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 $697 per night (USD)
VRBO
Click For Pricing
VRBO
In the Heart of Osterville Village, Newly renovated, Pets considered RPMS087
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Michelle Sylvia rental collection. LOCATION!! In the Heart of Osterville Village. Walk to town, shopping, dining, beac ...
Click For Pricing
VRBO
From $475 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! Chef's kitchen and updated bathrooms. Short drive to beach, pond or charming Oster ...
From $475 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Osterville Escape to our Spacious Family Getaway. Barnstable Beach pass included
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Comfortable Family Home in a quiet Osterville neighborhood. Great for your Cape Cod summer vacation. Comfortably sleeps ...
From $412 per night (USD)
VRBO
From $1811 per night (USD)
VRBO
Overlooking Nantucket Sound, Classic Victorian Era home
Bedrooms:
3
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 $1811 per night (USD)
VRBO
From $304 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 $304 per night (USD)
VRBO
From $327 per night (USD)
VRBO
THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Quiet three bedroom, two full bath Cape located on a dead-end street in the quaint town of Osterville. First floor inclu ...
From $327 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Osterville~Newly Renovated with central AC and beach pass
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Osterville ~Total renovation recently completed and now available for the 2025-2026 rental season. Minimum age to rent i ...
From $515 per night (USD)
VRBO
From $1518 per night (USD)
VRBO
Beautiful designed, newly constructed home- all the amenities, close to beaches
Bedrooms:
4
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 $1518 per night (USD)
VRBO
$\The Half Shell\ Cottage in Osterville Village$
From $1360 per night (USD)
VRBO
\"The Half Shell\" Cottage in Osterville Village
Bedrooms:
1
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 $1360 per night (USD)
VRBO
From $4555 per night (USD)
VRBO
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
Bedrooms:
5
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 $4555 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Enchanting 2 Bedroom Cottage - 1 block to Village Center-BEACH PASS-Weekly only
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Completely renovated 2 Bedroom, 1.5 Bath Duplex just one block to Osterville Village. Living Room with vaulted ceilings, ...
From $459 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1195 per night (USD)
VRBO
Osterville Cape Cod-Style Home - One Block from North Bay!
Bedrooms:
5
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 $1195 per night (USD)
VRBO
From $916 per night (USD)
Expedia
Beach pass included • Modern 3BR Osterville retreat, walkable to village center
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy modern Cape Cod living in this private 3-bedroom, 2-bath ranch-style home in Osterville. The home sleeps up to 8 a ...
From $916 per night (USD)
Expedia
From $4188 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 $4188 per night (USD)
VRBO
From $1235 per night (USD)
VRBO
Impressive Osterville Residence - Ideal Location
Bedrooms:
5
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 $1235 per night (USD)
VRBO
From $1991 per night (USD)
VRBO
Heated Private Pool, Walk to Beach & Shops, fully renovated house
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
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 $1991 per night (USD)
VRBO
From $1524 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 $1524 per night (USD)
VRBO
From $933 per night (USD)
VRBO
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
The perfect setting for enjoying summertime in Osterville. This comfortable three bedroom home is overflowing with charm ...
From $933 per night (USD)
VRBO
From $1528 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
Waterfront-5BD, with bonus room-Deep Water Dock-Screen Porch-Close to Osterville Village-Beach Pass * * * * See ...
From $1528 per night (USD)
VRBO
From $1921 per night (USD)
VRBO
Amazing updated waterfront home located in Osterville with a private dock, elevator and AC.
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Waterfront- 7BD-Deep Water Dock-Close to Osterville Village-A/C, Elevator and Beach Pass * * * * See end of thi ...
From $1921 per night (USD)
VRBO
From $1123 per night (USD)
VRBO
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
Bedrooms:
4
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 $1123 per night (USD)
VRBO
From $774 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 $774 per night (USD)
VRBO
From $2793 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 $2793 per night (USD)
Expedia
From $1728 per night (USD)
VRBO
Seasons by the Sea: Fully Renovated Luxury Cape Cod Home
Bedrooms:
3
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 $1728 per night (USD)
VRBO
From $502 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 $502 per night (USD)
VRBO
From $737 per night (USD)
VRBO
Osterville - close to town & beach, AC, beach pass
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Enjoy summertime in this completely renovated spacious Osterville home on a quiet side street. Air conditioning was adde ...
From $737 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Charming cottage near Osterville Village and Dowses beach RPMS094
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Michelle Sylvia rental collection home. This is the most charming and updated cottage in the "village" that you will fin ...
From $545 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Blossom Beach Cottage is a peaceful retreat in the heart of Osterville Village. Walking distance to Shopping, Dining, Po ...
From $528 per night (USD)
VRBO
From $750 per night (USD)
Expedia
Osterville Retreat – A/C, WiFi & Pet-Friendly
Bedrooms:
3
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 $750 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Swing Set, Plunge pool, and large yard await!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 21012 - Oyster Circle: Swing Set, Plunge pool, and large yard await! The Space: Over the bridge to Ostervi ...
From $577 per night (USD)
VRBO
From $6401 per night (USD)
Expedia
The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Michelle Sylvia high end Luxury collection rental home. Welcome to Osterville! This spacious newly renovated rental prop ...
From $6401 per night (USD)
Expedia
From $1460 per night (USD)
VRBO
Charming 4BR Osterville Home, Walk to Pond, 2 mi to beach, Hot Tub & Beach Pass
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your perfect Cape escape! Nestled in a quiet, family-friendly neighborhood in Osterville, this beautifully a ...
From $1460 per night (USD)
VRBO
Click For Pricing
VRBO
Large home in the heart of Osterville Village, sleeps 11
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
LARGE-6BD Home--A/C, Amazing Location- Walk to Osterville Village and Dowses Beach-Great Private Backyard * * * * ...
Click For Pricing
VRBO
From $2640 per night (USD)
VRBO
Luxury rental with pool. Close to village and beach RPMS157
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Michelle Sylvia luxury collection. Stunning Coastal Luxury in Osterville - 468 Wianno Ave Experience Cape Cod living at ...
From $2640 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Private Saltwater Pool, Game Room, near Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 21017 - Salt Wind: Private Saltwater Pool, Game Room, near Beaches! The Space: Your Cape Cod escape begins ...
From $473 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Little Gem walking distance to Osterville Village
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Your Ideal Vacation Rental in Osterville This adorable property blends comfort, convenience, and coastal cha ...
From $424 per night (USD)
VRBO
From $7713 per night (USD)
Expedia
NEW for 2026! Views of Cotuit Bay, pool, dock, beach area & hot tub RPMS156
Bedrooms:
4
Bathrooms:
7
Sleeps:
15
Exclusive Michelle Sylvia Luxury Collection | First Time Offered Welcome to 835 Old Post Road in Cotuit, an exceptional ...
From $7713 per night (USD)
Expedia
Click For Pricing
VRBO
Osterville pool rental near beach. Back yard paradise!! RPMS138
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Michelle Sylvia luxury collection. Exquisite 6-bedroom luxury pool home nestled on Sea View Avenue in Osterville, Cape ...
Click For Pricing
VRBO
From $612 per night (USD)
VRBO
Osterville, Private Yard, Close to Osterville Village, Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
NEW LISTING – Osterville Retreat – Large Private Yard – Close to Village, Beach & Pond * * * * See end of this ...
From $612 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Cape Cod getaway near Craigville Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax in this sunny Osterville home near village cafés and 3 beaches. The open main floor has a roomy living area and ea ...
From $461 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Walk to Shops & Dining: Cozy Osterville Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
BBQ Ready | Recently Renovated | Convenient Main St Location Step into Cape Cod living at this 2-bed, 1-bath Osterville ...
From $467 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Private & Serene Stay 2-bedroom studio - Osterville - AC - Free Beach Pass - W/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cozy, newly renovated 2025 home with a private entrance and immediate stairs leading to the second floor, ...
From $250 per night (USD)
VRBO
From $784 per night (USD)
VRBO
Classic Cape Cod Charm in the heart of Osterville Village.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the best of Osterville from this immaculate 3 bedroom home just a short walk to the heart of the village shops and ...
From $784 per night (USD)
VRBO
From $623 per night (USD)
VRBO
Private Pool, Central AC, Dog Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 21001 - Whisked Away: Private Pool, Central AC, Dog Friendly! The Space: Welcome to Whisked Away, your qui ...
From $623 per night (USD)
VRBO
From $1244 per night (USD)
Expedia
Elegant Family Osterville Retreat Near Dowses Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Escape to this beautifully appointed Osterville retreat—where coastal charm meets comfort and thoughtful desig ...
From $1244 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Osterville Gem Steps to Main St! Relax fireside
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Mi to Beach | Easy Access to Shops & Dining | Updated Interior Craving a classic Cape Cod experience? This 2-bed, 1-b ...
From $467 per night (USD)
VRBO
From $690 per night (USD)
Expedia
Osterville Retreat, Hot Tub, Beach Pass, 6 min from beach, 3 BR
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Consider this house your home away from home while you visit Barnstable. With 3 bedrooms including 2 queen beds and 1 fu ...
From $690 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Charming home with open layout, deck, grill, AC, W/D, & yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Wisteria Haven The Space: Welcome to your perfect Cape Cod getaway in Osterville! This delightful 3-bedroo ...
From $448 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Cape escape with patio, grill, firepit, outdoor dining, W/D
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Osterville Odyssey The Space: Make your home away from home at this central Cape Cod retreat. Ideally situ ...
From $552 per night (USD)
Expedia
From $2316 per night (USD)
VRBO
Rare Osterville Waterfront Compound - Private Beach, Dock, Hot Tub & Sunset View
Bedrooms:
7
Bathrooms:
8
Sleeps:
20
Welcome to Anchor to Windward, a private waterfront retreat in the heart of Osterville. Set on two acres overlooking Wes ...
From $2316 per night (USD)
VRBO
From $887 per night (USD)
VRBO
Perfect Family Retreat in Idyllic Osterville. Steps to the town center and beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your comfortable vacation home, the perfect place to gather with family and friends! This coastal 4-bedroom ...
From $887 per night (USD)
VRBO
From $563 per night (USD)
VRBO
Cozy Getaway with Beach Pass & Sunroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
3 Bedroom - 1.5 Baths - Sleeps 6 During peak summer weeks, it is typical for our properties to require a 7-night stay, S ...
From $563 per night (USD)
VRBO
From $996 per night (USD)
VRBO
5 minutes to beach, newly redone house w hot tub/screening room in osterville
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
5 minutes to beach, beach pass, Jacuzzi, Game and Screening room! Enjoy all the cuteness of Osterville village, hit th ...
From $996 per night (USD)
VRBO
From $203 per night (USD)
VRBO
2 Mi to Dowses Beach! Couples Haven in Osterville
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your charming cottage retreat in Osterville, MA, where relaxation meets adventure on picturesque Cape Cod. Wh ...
From $203 per night (USD)
VRBO
From $1956 per night (USD)
Expedia
Elevated Osterville Escape with Heated Pool RPAM128
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
JUST LISTED IN JULY OF 2026! Welcome to effortless Cape Cod luxury at 21 Cockachoisett Lane in Osterville. Newly built ...
From $1956 per night (USD)
Expedia

Search Your Destination Now!

Oysterville Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 60 Rentals