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Vacation Rentals in Osterville, MA
Vacation Rentals
USA
Massachusetts (MA)
Cape Cod
Osterville Vacation Rentals
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Bedrooms
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Bathrooms
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Amenities
Internet or Wifi (63)
Air Conditioning (62)
Grill (53)
Washer/Dryer (53)
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Suitability
Kid friendly (61)
Pet friendly (22)
Wheelchair access (0)
Elder access (0)
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Property type
Vacation Rental House (63)
Condominium/Apartment (0)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (5)
Private Chef (0)
Private Beach (0)
Ski In/Ski Out (0)
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Distance from
5 mi
Osterville Village Library
Osterville Historical Society Museum
Skunknett River Wildife Sanctuary
A. Stanley Wheelock Antiques
Armstrong-Kelley Park
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63 rentals
in Osterville.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
20
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Close to beautiful Dowses beach, central AC, and pet friendly!
1
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 6
Match:
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Charming cottage steps to Osterville village. Near Dowses beach. RPMS094
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Prime Osterville Location - Clean and Comfortable Family Home
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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The Cape Escape Summa
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Cheerful 3 Bedroom Home in Osterville - Great Deck
2
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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In town Osterville village location
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
15
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
5
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Contemporary Gem with Private Pool!
4
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Cozy Cape-style home in private neighborhood
1
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
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A wonderful place with A wonderful beach to spend a vacation !!
11
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Walk to Joshua Pond Beach & Downtown!
4
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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Osterville village newly renovated 3 +bed 6 acres
2
Rental Home
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4 bedrooms
6 bathrooms
Sleeps 8
Match:
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Heated Private Pool, Walk to beach & shops, fully renovated house
48
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 11
Match:
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WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!
19
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
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New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
2
Rental Home
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4 bedrooms
6 bathrooms
Sleeps 9
Match:
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Osterville Cape Cod-Style Home - One Block from North Bay!
10
Rental Home
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6 bedrooms
6 bathrooms
Sleeps 10
Match:
Sleeps
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Historic Home in Prime Osterville Village Location: Three bedrooms, Sleeps 6
6
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Lovely Osterville Home With New Gunite Pool and Beach Pass.
3
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 9
Match:
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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
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Unbeatable location, views and water access from this rare family compound
3
Rental Home
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8 bedrooms
8 bathrooms
Sleeps 20
Match:
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"The Half Shell" Cottage in Osterville Village
9
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Amazing updated waterfront home located in Osterville with a private dock
Rental Home
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1 bedroom
1 bathroom
Sleeps 12
Match:
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The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104
Rental Home
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6 bedrooms
5 bathrooms
Sleeps 12
Match:
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Enchanting 2 Bedroom Cottage - 1 block to Village Center
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Large home in the heart of Osterville Village, sleeps 11
Rental Home
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6 bedrooms
4 bathrooms
Sleeps 11
Match:
Sleeps
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3 bedroom Osterville home, Beach Pass Included
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Swing Set, Plunge pool, and large yard await!
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Renovated & Comfortable Osterville Home - Close to Bakery
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 9
Match:
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Quaint Osterville home with Swim Spa
7
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Expansive Cape Cod Family Retreat
1
Rental Home
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11 bedrooms
7 bathrooms
Sleeps 22
Match:
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
3
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Brand New Osterville Home! Central AC, Walk/Bike to town or beach, Sleeps 10
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass
10
Rental Home
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6 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Updated with Pool in Charming Osterville Village: 032-Ov
1
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
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Cape escape with patio, grill, firepit, outdoor dining, W/D
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Beautiful designed, newly constructed home- all the amenities, close to beaches
1
Rental Home
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4 bedrooms
5 bathrooms
Sleeps 8
Match:
Sleeps
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Great Outdoor Space Central AC WIFI Family Friendly
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach
2
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Private Nantucket style home with heated pool and beach pass
10
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village
Rental Home
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4 bedrooms
5 bathrooms
Sleeps 7
Match:
Sleeps
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Impressive Osterville Residence - Ideal Location
Rental Home
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6 bedrooms
6 bathrooms
Sleeps 15
Match:
Sleeps
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Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
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Perfect Vacation Getaway!
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Charming Cottage Getaway
54
Rental Home
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2 bedrooms
1 bathroom
Sleeps 3
Match:
Sleeps
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Wonderful Osterville home close to Joshuas pond ~New to VRBO~
1
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
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Perfectly Located Osterville Heights Rental RPAM021
8
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Charming Carriage House on Private Oceanfront Estate
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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1
2
Showing results 1-50 of 63
Frequently Asked Questions about Osterville
Do any vacation rentals in Osterville have a pool?
Yes, here are some popular vacation rentals in Osterville that have a pool:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Close to beautiful Dowses beach, central AC, and pet friendly!
Charming cottage steps to Osterville village. Near Dowses beach.
See all vacation rentals with a pool in Osterville on Tripadvisor
Do any vacation rentals in Osterville have internet access?
Yes, here are some popular vacation rentals in Osterville that have internet access:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Close to beautiful Dowses beach, central AC, and pet friendly!
Charming cottage steps to Osterville village. Near Dowses beach.
See all vacation rentals in Osterville on Tripadvisor
What are the best pet friendly rentals in Osterville?
The best pet friendly rentals in Osterville are:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Close to beautiful Dowses beach, central AC, and pet friendly!
The Cape Escape Summa
See all pet friendly vacation rentals in Osterville on Tripadvisor
What are some great rentals in Osterville that are kid friendly?
Some of the most popular kid friendly rentals in Osterville are:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Close to beautiful Dowses beach, central AC, and pet friendly!
Charming cottage steps to Osterville village. Near Dowses beach.
See all kid friendly vacation rentals in Osterville on Tripadvisor
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