Osterville Vacation Rentals from SAR 392: 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

Carrie B.

SAR 3,535 total

includes taxes & fees

13 Nov - 14 Nov

A golf course with a clubhouse, a lake, and surrounding trees.

2. The Club at New Seabury

New Seabury

Kathleen

SAR 633 total

includes taxes & fees

17 Nov - 18 Nov

A pool area with lounge chairs and flags.

3. The Cove at Yarmouth by Westgate Resorts

West Yarmouth

Manizheh

SAR 392 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Marston Mills

Sarah K.

SAR 1,463 total

includes taxes & fees

22 Nov - 23 Nov

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

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

Sandwich

Sean H.

SAR 1,456 total

includes taxes & fees

17 Nov - 18 Nov

A living room with a sectional sofa, a wooden coffee table, a blue and white rug, and a window with a 'BEACH' sign.

6. Great Home Close to Craigville Beach

Barnstable

James B.

SAR 2,332 total

includes taxes & fees

4 Dec - 5 Dec

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

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

Barnstable

Jen M.

SAR 1,991 total

includes taxes & fees

10 Dec - 11 Dec

An aerial view of a beach with a boat dock, a house, and dense forest.

8. Historic 5BR Mid Cape w/ Private Lake Access

Barnstable

Camila P.

SAR 2,165 total

includes taxes & fees

15 Nov - 16 Nov

A beach with sand, flowers, and a clear sky.

9. Beach Pass Included!

Barnstable

Sara D.

SAR 1,160 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Barnstable

Jamie C.

SAR 3,488 total

includes taxes & fees

13 Nov - 14 Nov

A kitchen with a dining area, a ceiling fan, and a view to an outdoor patio.

11. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

Sandwich

SAR 1,400 total

includes taxes & fees

12 Dec - 13 Dec

12. Entire Hyannis Home - Near Downtown & Beaches

Barnstable

Ellie M.

SAR 1,761 total

includes taxes & fees

1 Dec - 2 Dec

A kitchen with a central island, white cabinets, a gas stove, and a sink.

13. Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Barnstable

Austin S.

SAR 4,046 total

includes taxes & fees

13 Nov - 14 Nov

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

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

Seconsett Island

Michele M.

SAR 1,566 total

includes taxes & fees

15 Nov - 16 Nov

A beach with a boat labeled MS1284HB and a covered area.

15. Secluded-Entire 2nd floor Suite with Private Bath

Barnstable

Brandon S.

SAR 924 total

includes taxes & fees

15 Nov - 16 Nov

A kitchen with white cabinets, a black and white checkered floor, a ceiling fan, and a green lamp.

16. Sal's Place

Hyannis

SAR 1,524 total

includes taxes & fees

18 Nov - 19 Nov

A wooden deck with a table and chairs, overlooking a body of water and trees.

17. Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Barnstable

Molly R.

SAR 4,161 total

includes taxes & fees

13 Nov - 14 Nov

A wooden deck with a wooden bench, a railing, and a window.

18. Hyannis Hideaway in Cape Cod

Barnstable

Nathalie M.

SAR 3,024 total

includes taxes & fees

13 Nov - 14 Nov

A wooden interior with a dining area set for a meal, featuring a table with plates, glasses, and cutlery.

19. Charming Family-friendly Getaway in Sandwich!

Sandwich

SAR 1,463 total

includes taxes & fees

15 Nov - 16 Nov

A fire pit surrounded by white chairs and a table, set on a gravel area with trees in the background.

20. Cozy, vacation home in a charming duplex cottage

Yarmouth

Sarah B.

SAR 1,306 total

includes taxes & fees

1 Dec - 2 Dec

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Top Osterville Hotel Reviews

Vineyard Harbor Motel - Private Beach

10/10 Excellent

"I enjoyed the property. My room was very clean and the property is so close to everything. I will definitely stay there again."

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"When you think botique hotel this is what you're hoping for. Every detail made sense. The hotel itself is a destination. We stayed for one night while visiting the Cape during shoulder season. It was absolutely lovely. The room was comfortable and clean and so cute. Loved the outside patio and the view of the bay. The staff were amazing and so friendly. I would not hesitate to book this hotel. We wanted to use the indoor pool, which was amazing, but we were so exhausted we ate dinner at a local Italian place and came back and passed out!"

Hyannis Harbor Hotel

8/10 Good

"We were only at The Harbor House for a brief overnight stay. Our room, 3010, was very nice and clean. However, the view out of our window was of the parking lot and all the garbage dumpsters. If this were a summer rental for us, I would have been extremely disappointed! Given the prices charged and the new additional parking fee, I feel that the view issue should have been disclosed at the time of booking the room."

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

10/10 Excellent

"We stayed two nights and our stay was excellent. The hotel is very clean and bright, our room was very pleasant and a nice size. We had plenty of room for all our stuff and the bed was quite comfortable. The bathroom was roomy and the shower was excellent! Breakfast was pretty much the regular hotel breakfast, everything was hot and plentiful. We have stayed before and will most likely be back in the future. It's also really nice to be able to walk to the Cape Cod Mall in less than five minutes."

Bayside Resort Hotel

10/10 Excellent

"The motel is an older facility that most likely has been renovated and well maintained. It is very clean. The room was spotless, Bathrooms spotless and good hot water with good pressure. Beds (we got the 2 twins) were medium in firmness, comfortable. No problems with room temp. The indoor pool area, pool and hot tub were very clean and enjoyable. The gym has several cardio machines, a few dumbbells and bench and a budget universal type machine. It was fine. They have an arcade (we looked but did not use) and the instructions are on the wall before you enter the room, It is a minimum of $25 on your card. That should give someone or a couple a bit of playtime. The breakfast dining area was very clean. My wife has an eye for those things and nothing bothered her and that was a huge benefit. The breakfast had a reasonable amount of choices. This is not an AA breakfast but I ate, it was fine and I was filled. Massachusetts has a $12 tax you have to pay and the motel has a $50 (pending only) fee I guess incase you damage the room or do not return the electronic keys (which we had no problem with) They put $62 on my CC on our arrival the 3rd; we left the 4th. On the 5th a $12 charge went onto my CC. I called and was told the $62 was pending only and by the 7th, only the $12 charge was on my CC. I would happily stay there again. -CD"

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. Serene Haven w/ No Shared Spaces | Cape Cod

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

6. Great Home Close to Craigville Beach

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

8. Historic 5BR Mid Cape w/ Private Lake Access

9. Beach Pass Included!

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

11. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

12. Entire Hyannis Home - Near Downtown & Beaches

13. Spacious Lake House for Large Groups w Private Acre+ short path to Lake

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

15. Secluded-Entire 2nd floor Suite with Private Bath

16. Sal's Place

17. Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

18. Hyannis Hideaway in Cape Cod

19. Charming Family-friendly Getaway in Sandwich!

20. Cozy, vacation home in a charming duplex cottage

Find vacation rentals that suit your style

Top Osterville Hotel Reviews

Vineyard Harbor Motel - Private Beach

Margaritaville Resort Cape Cod

Uncommoner Hotel by Reverie Boutique Collection

Cape Sands Inn

Hyannis Harbor Hotel

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Bayside Resort Hotel

Faraway Martha's Vineyard

Sunbird Cape Cod Resort

Frequently asked questions

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