Osterville Vacation Rentals from ￥22,753: Search Short-Term Rentals

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Our top choices for Osterville vacation rentals

A beach with a clear sky and a lifeguard tower in the distance.

1. Beach pass included • Modern 3BR Osterville retreat, walkable to village center

Osterville

Elizabeth C.

￥143,827 total

includes taxes & fees

Oct 1 - Oct 2

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

2. The Club at New Seabury

New Seabury

Kathleen

￥38,911 total

includes taxes & fees

Oct 11 - Oct 12

A pool area with lounge chairs and flags.

3. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

BELKIS

￥22,753 total

includes taxes & fees

Oct 26 - Oct 27

A modern living room with a sofa, chairs, a coffee table, and a dining area.

4. New Seabury Cape Condo + Pool & Beach Escape

New Seabury

Jeff V.

￥50,738 total

includes taxes & fees

Sep 30 - Oct 1

A sandy beach with a calm lake and a forested hill in the background.

5. Charming 3-bedroom house in lovely Barnstable

Barnstable

Cailee B.

￥109,772 total

includes taxes & fees

Oct 12 - Oct 13

A kitchen with white cabinetry, a double-door refrigerator, and a glass-fronted cabinet with dishes.

6. Serene Haven w/ No Shared Spaces | Cape Cod

Marston Mills

Dana S.

￥64,938 total

includes taxes & fees

Sep 27 - Sep 28

A compact living space with a kitchen, dining area, and seating area.

7. 1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

Hyannis

Jill S.

￥58,509 total

includes taxes & fees

Oct 2 - Oct 3

A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

8. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Sandwich

Sean H.

￥71,733 total

includes taxes & fees

Oct 21 - Oct 22

A wooden deck with a table and chairs, surrounded by a wooden fence and large windows.

9. Classic Cape Escape in Charming Cotuit

Contuit

Michelle

￥159,190 total

includes taxes & fees

Oct 6 - Oct 7

A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

10. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable

Jen M.

￥78,879 total

includes taxes & fees

Sep 27 - Sep 28

A single-story house with a front porch, a number '5' on the door, and a well-maintained lawn.

11. Cozy One Bedroom Cabin on Cape Cod Campground!

Bass River

Rick F.

￥37,862 total

includes taxes & fees

Sep 26 - Sep 27

A beach with clear blue water and a sandy shore.

12. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable

Jim C.

￥116,474 total

includes taxes & fees

Sep 28 - Sep 29

A boat docked at a concrete pier with a sandy shore in the background.

13. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Seconsett Island

Kian S.

￥72,095 total

includes taxes & fees

Sep 27 - Sep 28

14. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Hyannis

"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...

Christa

￥57,567 total

includes taxes & fees

Oct 2 - Oct 3

A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

15. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Dennis Port

Laurie and Rick A.

￥68,326 total

includes taxes & fees

Oct 1 - Oct 2

A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

16. Charming studio in tranquil Falmouth with AC

Falmouth

Harry H.

￥37,496 total

includes taxes & fees

Sep 27 - Sep 28

A compact kitchen with a refrigerator, microwave, and sink.

17. Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Yarmouth

Nicholas

￥75,354 total

includes taxes & fees

Sep 28 - Sep 29

A modern kitchen with a large island, stainless steel appliances, and grey cabinetry.

18. New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Barnstable

Charbel T.

￥155,238 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living room with a large sectional sofa, a coffee table, and a patterned rug. There is a kitchen area with white cabinets and a dining table. A wooden staircase leads to an upper level.

19. Beach Lovers Escape

Yarmouth

alex f.

￥110,740 total

includes taxes & fees

Oct 1 - Oct 2

A beach with a wooden fence and people walking along the shore.

20. Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Dennis

Shelby V.

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Top Osterville Hotel Reviews

Inn on the Square

10/10 Excellent

"We enjoyed the outdoor lounge area and indoor pool very much. Clean, comfortable bedding and a small fridge. Across the street from a great coffee shop and walking distance to the center of town perfect."

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent

"This has been our go to on Cape Cod for many, many years. Rooms are clean and well maintained, a/c is great, and doesn’t turn on and off like some places. The sink and mirror is outside the bathroom, so one person can get ready, while another showers. Each room has a mini fridge for food and drinks. Pool and hot tub are wonderful after a long day in the sun. Yummy drinks and flatbreads available at the bar truck. Located in a convenient spot, close to restaurants, shops, and mini golf. Beaches are a short drive away."

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"Loved this place. It was clean, well maintained, beautiful and unique, comfortable, and had so many ways to relax or have fun. The outdoor areas were great from the swimming pool to the Adirondack chairs by the bay. We did eat breakfast at the cafe and feel if they’d use a number system or some sort of way to identify peoples food it would’ve been a much better and efficient experience."

Hyannis Travel Inn

10/10 Excellent

"The gentleman on reception was amazing! So helpful! Gave us some good tips for getting to Nantucket and Martha’s Vineyard! He also checked us in early which was great and allowed us to park all day after we checked out! So accommodating!!! The gentleman really made this stay for us! So friendly and helpful! Down to earth guy and chatted to us for ages!"

Summercamp

8/10 Good

"Nice room and wonderful front porch with a view of the water. Close to many restaurants and shops in town. The hotel could have provided better information on how to get into the property. After circling the hotel, we managed to find a parking spot and go in. Then we were told that our reserved parking spot was past the "do not enter" sign. Knowing that ahead of time would have saved a lot of tension. It is important to reserve a parking spot."

Faraway Martha's Vineyard

8/10 Good

"A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)"

Find out more about Osterville

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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?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

How many vacation rentals are there in Osterville?

With 59 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.

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Check prices for these dates

Our top choices for Osterville vacation rentals

1. Beach pass included • Modern 3BR Osterville retreat, walkable to village center

2. The Club at New Seabury

3. The Cove at Yarmouth by Westgate Resorts

4. New Seabury Cape Condo + Pool & Beach Escape

5. Charming 3-bedroom house in lovely Barnstable

6. Serene Haven w/ No Shared Spaces | Cape Cod

7. 1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

8. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

9. Classic Cape Escape in Charming Cotuit

10. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

11. Cozy One Bedroom Cabin on Cape Cod Campground!

12. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

13. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

14. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

15. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

16. Charming studio in tranquil Falmouth with AC

17. Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

18. New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

19. Beach Lovers Escape

20. Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Find vacation rentals that suit your style

Top Osterville Hotel Reviews

Inn on the Square

Freebird Motor Lodge by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

Hyannis Travel Inn

Hyannis Harbor Hotel

Holiday Hill Inn & Suites

Riviera Beach Resort

Summercamp

Faraway Martha's Vineyard

Find out more about Osterville

Frequently asked questions

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