Search Vacation Homes in Osterville

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Homes in Osterville

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Fridge, microwave, oven, stovetop

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
10.0 out of 10, Exceptional, (22)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is ￥19,552
￥102,466 total
includes taxes & fees
Oct 7 - Oct 8
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
The Mermaid House @ OBC Cape Cod Beach Resort-8PPL.HotTub
Fridge, microwave, oven, stovetop

The Mermaid House @ OBC Cape Cod Beach Resort-8PPL.HotTub

8.0 out of 10, Very Good, (7)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
The price is ￥7,507
￥76,617 total
includes taxes & fees
Oct 8 - Oct 9
The Mermaid House @ OBC Cape Cod Beach Resort-8PPL.HotTub
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

Cozy Large Home in Harwich with Patio near Wequassett Resort

9.8 out of 10, Exceptional, (10)
"We had a great time here - the kids’ room is truly special!"
The price is ￥19,846
￥72,633 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Large Home in Harwich with Patio near Wequassett Resort
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Beach

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
The price is ￥26,347
￥56,378 total
includes taxes & fees
Oct 27 - Oct 28
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Exterior detail

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (34)
"The location was a perfect fit for our needs. "
The price is ￥19,871
￥141,170 total
includes taxes & fees
Oct 8 - Oct 9
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is ￥25,758
￥98,648 total
includes taxes & fees
Oct 5 - Oct 6
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Coastal Haven in West Dennis
Fridge, microwave, oven, stovetop

Coastal Haven in West Dennis

2.0 star property
10.0 out of 10, Exceptional, (3)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
The price is ￥37,865
￥89,801 total
includes taxes & fees
Oct 4 - Oct 5
Coastal Haven in West Dennis
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Fridge, microwave, oven, stovetop

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

9.6 out of 10, Exceptional, (49)
"Enjoyed the stay at the house very much. The house was as described and very clean. Great location and we plan on staying again in the future."
The price is ￥19,429
￥76,923 total
includes taxes & fees
Oct 7 - Oct 8
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Cozy Riverfront Stay in Wareham
Fridge, microwave, oven, stovetop

Cozy Riverfront Stay in Wareham

10.0 out of 10, Exceptional, (2)
"We had a misunderstanding about the property. We thought it had laundry facilities, but our unit did not. Property manager quickly solved our problem!"
The price is ￥25,420
￥64,399 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Riverfront Stay in Wareham
Thompson House Cape Cod
Fridge, microwave, oven, stovetop

Thompson House Cape Cod

3.0 star property
The price is ￥59,539
￥184,573 total
includes taxes & fees
Oct 16 - Oct 17
Thompson House Cape Cod
Charming 3 bed room with magnificent views & large deck
Exterior

Charming 3 bed room with magnificent views & large deck

8.0 out of 10, Very Good, (3)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
The price is ￥20,607
￥58,120 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3 bed room with magnificent views & large deck
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Beach nearby, sun loungers, beach towels

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

10.0 out of 10, Exceptional, (123)
"Beautiful property and the hosts were great! "
The price is ￥36,753
￥56,324 total
includes taxes & fees
Oct 6 - Oct 7
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Seaside Getaway - Harwichport Beachhouse
Beach nearby

Seaside Getaway - Harwichport Beachhouse

9.8 out of 10, Exceptional, (8)
"Great location great property"
The price is ￥32,985
￥71,275 total
includes taxes & fees
Oct 5 - Oct 6
Seaside Getaway - Harwichport Beachhouse
Sal's Place
Family House, Private Bathroom, Pool View | Shared kitchen

Sal's Place

2.0 star property
The price is ￥58,804
￥84,942 total
includes taxes & fees
Oct 16 - Oct 17
Sal's Place
Charming studio in tranquil Falmouth with AC
Interior

Charming studio in tranquil Falmouth with AC

The price is ￥17,663
￥27,797 total
includes taxes & fees
Oct 5 - Oct 6
Charming studio in tranquil Falmouth with AC
Oldest Town of Cape Cod In The Historic District
Fridge, microwave, oven, stovetop

Oldest Town of Cape Cod In The Historic District

9.2 out of 10, Wonderful, (12)
"The property has a great location and was very well kept up. We were out a lot at a conference but really enjoyed the property and the owner. "
The price is ￥18,399
￥57,781 total
includes taxes & fees
Nov 2 - Nov 3
Oldest Town of Cape Cod In The Historic District
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
2 bedrooms, desk, iron/ironing board, WiFi

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

8.8 out of 10, Excellent, (3)
"The property met our needs very nicely. The bathrooms were dated, as was he most of the home, but it was clean and very comfortable. We enjoyed staying there very much."
The price is ￥29,438
￥67,385 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Property grounds

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

8.8 out of 10, Excellent, (5)
"Our family stayed here for a quick Cape get away at the end of summer. The host was responsive and kind. The property was in a great location with a kitchen that had everything we needed. Great spot"
The price is ￥17,368
￥70,752 total
includes taxes & fees
Oct 13 - Oct 14
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.
Marina

Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

10.0 out of 10, Exceptional, (3)
"Excellent house. Well supplied with all essentials plus incidentals. Would definitely stay again!"
The price is ￥32,455
￥78,999 total
includes taxes & fees
Oct 7 - Oct 8
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.
Make this charming, modern retreat your home away from home!!
Fridge, microwave, oven, stovetop

Make this charming, modern retreat your home away from home!!

9.6 out of 10, Exceptional, (4)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
The price is ￥21,931
￥45,871 total
includes taxes & fees
Oct 13 - Oct 14
Make this charming, modern retreat your home away from home!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osterville Hotel Reviews

Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"The staff was very friendly and helpful. Loved the pool and hot tub! It is located in the heart of Edgartown. Easy access to everything! Stayed here a few years ago before they renovated it. They did a great job! Will be back next year! "
elizabeth 2-night trip
Posted 1 day ago
Faraway Martha's Vineyard

Find out more about Osterville

Find out more about Osterville

Osterville Vacation Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia