Osterville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Osterville vacation rentals

Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (349 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The price is ￥22,942
￥26,257 total
includes taxes & fees
Feb 17 - Feb 18
The Club at New Seabury
Indoor spa tub

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (124 reviews)
"The front desk staff are So pleasant to deal with. Pool is huge and the kids loved the game room"
United States
PAUL
The price is ￥22,819
￥26,117 total
includes taxes & fees
Jan 31 - Feb 1
Brewster Green Resort
Beach nearby

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (63 reviews)
"Very nice location and the unit was clean and comfortable. "
United States
Jeanne M.
The price is ￥9,188
￥48,611 total
includes taxes & fees
Feb 5 - Feb 6
Quaint condo near private beach access with fireplace - close to dining
Indoor pool, seasonal outdoor pool

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, (248 reviews)
"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
The price is ￥16,822
￥19,252 total
includes taxes & fees
Feb 1 - Feb 2
The Cove at Yarmouth by Westgate Resorts
TV, fireplace, foosball, table tennis

The Mermaid Cottage @ The Compound Beach Resort Habitat

The Mermaid Cottage @ The Compound Beach Resort Habitat
Cape Cod
8.0 out of 10, Very Good, (7 reviews)
"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.
The price is ￥7,810
￥79,542 total
includes taxes & fees
Mar 2 - Mar 3
The Mermaid Cottage @ The Compound Beach Resort Habitat
Exterior

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Onset
9.8 out of 10, Exceptional, (28 reviews)
"The Seaview suite was great! Clean and nicely appointed. Great views from the deck. "
United States
Lauren M.
The price is ￥21,914
￥59,032 total
includes taxes & fees
Feb 1 - Feb 2
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Interior

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
7.4 out of 10, Good, (6 reviews)
"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.
The price is ￥7,810
￥76,244 total
includes taxes & fees
Feb 1 - Feb 2
The Crab Cottage@The Compound Beach Resort Habitat
Interior

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (49 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is ￥15,161
￥29,281 total
includes taxes & fees
Feb 3 - Feb 4
The Nantucket Room Unit - #2
Terrace/patio

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

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (129 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is ￥38,288
￥58,677 total
includes taxes & fees
Jan 31 - Feb 1
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Beach nearby

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (41 reviews)
"Great place!"
United States
Michael P.
The price is ￥28,808
￥52,254 total
includes taxes & fees
Jan 31 - Feb 1
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Exterior

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (22 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is ￥21,914
￥59,032 total
includes taxes & fees
Feb 1 - Feb 2
Spacious and Bright , Very Close to Beach!
Interior

Eazy Breezy Beach Home

Eazy Breezy Beach Home
Dennis
7.6 out of 10, Good, (4 reviews)
"Great location"
United States
alyssa w.
The price is ￥19,297
￥34,880 total
includes taxes & fees
Jan 31 - Feb 1
Eazy Breezy Beach Home
Outdoor dining

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

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is ￥20,214
￥81,488 total
includes taxes & fees
Feb 3 - Feb 4
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Beach nearby, sun loungers, beach towels

Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Dennis
10.0 out of 10, Exceptional, (32 reviews)
"The place was adorable and the location was perfect. We could walk to the beach, to an amazing little bakery and it gave us great access to our weekend of wedding events.Irene had suggested sunset at Mayflower Beach and it was spectacular. We will be back in the future."
United States
Natalie D.
The price is ￥45,896
￥104,408 total
includes taxes & fees
Jan 31 - Feb 1
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Smart TV, books

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 reviews)
"We enjoyed our two night stay."
United States
Lonnie W.
The price is ￥15,315
￥54,512 total
includes taxes & fees
Jan 31 - Feb 1
Oldest Town of Cape Cod In The Historic District
Fridge, microwave, oven, stovetop

Beach Bungalow: Steps to Beach, Luxury Family Fun

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay with college friends for the weekend. Excellent location, house is beautiful as is neighborhood. Very clean and easy to access, host was attentive. Highly recommend!!"
United States
Beth G.
The price is ￥31,671
￥92,864 total
includes taxes & fees
Feb 1 - Feb 2
Beach Bungalow: Steps to Beach, Luxury Family Fun
Exterior

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"This was a great home, very clean and spacious rooms. Lots of hooks to hang towels and plenty of space to spread out!"
United States
Quinn S.
The price is ￥48,239
￥116,729 total
includes taxes & fees
Jan 31 - Feb 1
Family Cottage Close to Beach!!
Smart TV

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed
Yarmouth
10.0 out of 10, Exceptional, (3 reviews)
"My wife and I stayed here four days. This house is centrally located and in a good, safe neighborhood. It was clean and had all supplies needed such as towels, dish soap, laundry soap, paper towels etc.Would stay here again. "
United States
Todd M.
The price is ￥16,693
￥80,831 total
includes taxes & fees
Feb 2 - Feb 3
Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed
Interior

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is ￥24,810
￥75,722 total
includes taxes & fees
Feb 1 - Feb 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Interior

The Ocean View Room @ The Compound~Romantic Professional

The Ocean View Room @ The Compound~Romantic Professional
Cape Cod
The price is ￥7,658
￥35,421 total
includes taxes & fees
Feb 1 - Feb 2
The Ocean View Room @ The Compound~Romantic Professional
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Excellent,very clean "
Quezia 2-night trip
Posted 2 days ago
Margaritaville Resort Cape Cod

Find out more about Osterville

Search for holiday rentals in Osterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Osterville using one of the methods below:

  • View our selection of featured holiday rentals in Osterville
  • Use the map to find apartments and other holiday homes in the Osterville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osterville while they last

Look no further and take a look at our great range of rental properties in Osterville!

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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This vacation home rental outside of Osterville is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Osterville?

With 62 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.