Osterville Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Osterville vacation rentals

Interior
The Ocean View Room @ The Compound~Romantic Professional

The Ocean View Room @ The Compound~Romantic Professional

The Ocean View Room @ The Compound~Romantic Professional
2.0 star property
Wareham
$229 nightly
The price is $232
Feb 1 - Feb 2
Total with taxes and fees
The Ocean View Room @ The Compound~Romantic Professional
Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (344)
"The place was excellent"
United States
Delia
$147 nightly
The price is $169
Jan 19 - Jan 20
Total with taxes and fees
The Club at New Seabury
TV, fireplace, foosball, table tennis
The Mermaid Cottage @ The Compound Beach Resort Habitat

The Mermaid Cottage @ The Compound Beach Resort Habitat

The Mermaid Cottage @ The Compound Beach Resort Habitat
Wareham
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"
United States
Oscar B.
$504 nightly
The price is $521
Feb 1 - Feb 2
Total with taxes and fees
The Mermaid Cottage @ The Compound Beach Resort Habitat
Interior
The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Wareham
7.4 out of 10, Good, (6)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
$504 nightly
The price is $522
Jan 11 - Jan 12
Total with taxes and fees
The Crab Cottage@The Compound Beach Resort Habitat
On the beach, white sand
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (196)
"the room was clean and had everything you could need!"
United States
Katherine
$117 nightly
The price is $134
Jan 12 - Jan 13
Total with taxes and fees
InnSeason Resorts Captain's Quarters
Property grounds
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$293 nightly
The price is $324
Jan 12 - Jan 13
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (244)
"The staff are amazing! Love the amenities - the pool, recreation center, activities for the kids such as windchime arts and crafts. The arcade is always a hit. The Loft makes it so easy to not have to stress about a place to go to for dinner. The Cove is a great place for everyone! "
United States
Lauren
$129 nightly
The price is $147
Jan 11 - Jan 12
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
Smart TV, books
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
$629 nightly
The price is $720
Jan 16 - Jan 17
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Interior
The Nantucket Room Unit - #2

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
$174 nightly
The price is $191
Jan 9 - Jan 10
Total with taxes and fees
The Nantucket Room Unit - #2
Smart TV, books
Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.0 out of 10, Wonderful, (17)
"We really loved this place and I "
United States
Valerie D.
$310 nightly
The price is $355
Jan 9 - Jan 10
Total with taxes and fees
Oldest Town of Cape Cod In The Historic District
Pool
Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$468 nightly
The price is $518
Jan 9 - Jan 10
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
Indoor spa tub
Brewster Green Resort

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (123)
"The front desk staff are So pleasant to deal with. Pool is huge and the kids loved the game room"
United States
PAUL
$139 nightly
The price is $159
Jan 9 - Jan 10
Total with taxes and fees
Brewster Green Resort
Dining
Big Sandy Beachcomber

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
9.6 out of 10, Exceptional, (13)
"Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!"
United States
Ben L.
$350 nightly
The price is $391
Jan 12 - Jan 13
Total with taxes and fees
Big Sandy Beachcomber
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit
Bass River
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
$544 nightly
The price is $603
Jan 9 - Jan 10
Total with taxes and fees
Charming House by the Beach with Patio, Grill, FirePit
Beach nearby
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Falmouth
8.2 out of 10, Very Good, (24)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
$175 nightly
The price is $200
Jan 9 - Jan 10
Total with taxes and fees
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Interior
Eazy Breezy Beach Home

Eazy Breezy Beach Home

Eazy Breezy Beach Home
Dennis
9.4 out of 10, Exceptional, (3)
"Great location"
United States
alyssa w.
$201 nightly
The price is $230
Jan 9 - Jan 10
Total with taxes and fees
Eazy Breezy Beach Home
Beach
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (8)
"Beds were very comfortable. House had great beach chairs. Owner was easy to reach and gave us information about area. "
United States
Linda Q.
$461 nightly
The price is $527
Jan 16 - Jan 17
Total with taxes and fees
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Smart TV
Gold Anchor Cottage - private hot tub getaway!

Gold Anchor Cottage - private hot tub getaway!

Gold Anchor Cottage - private hot tub getaway!
Sandwich
10.0 out of 10, Exceptional, (5)
"Small cottage, but spacious vaulted ceilings and a great backyard hang out space with the hot tub. Close walk to public beach or parking nearby."
United States
Greg E.
$386 nightly
The price is $442
Jan 11 - Jan 12
Total with taxes and fees
Gold Anchor Cottage - private hot tub getaway!
Smart TV, fireplace, books
Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (12)
"Great stay!"
United States
Kevin B.
$482 nightly
The price is $552
Jan 12 - Jan 13
Total with taxes and fees
Modern Beach & Pond Getaway; Heart of Cape Cod
Private kitchen
Edgartown Designer Retreat

Edgartown Designer Retreat

Edgartown Designer Retreat
2.0 star property
Katama
$1,979 nightly
The price is $2,211
Jan 9 - Jan 10
Total with taxes and fees
Edgartown Designer Retreat
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.
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Top Osterville Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Amazing!"
Erika 1-night trip
Posted 3 days ago
Bayside Resort Hotel

Find out more about Osterville

Everything you need to know about Osterville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osterville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osterville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osterville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osterville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $134 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osterville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osterville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osterville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Osterville?

Yes, we give you a choice of vacation rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Osterville has to offer?

MOST CHIC SPOT! Your Martha's Vineyard Getaway!: This vacation home rental outside of Osterville is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Osterville?

With 55 Expedia vacation rentals, you're sure to find just the right place for your Osterville stay.

What’s there to see and do in Osterville?

Cape Cod Beaches and Dowses Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Public Beach and Main Street are a couple of places you'll find in the larger area.

What’s a vacation rental in Osterville like?

Vacation rentals are private properties you can book for a short or long stay in Osterville. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.