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Osterville Rentals

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1,101 Houses

271 Westwind Cir

Osterville house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$204

Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$496

Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location

Osterville apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$210

236B Smoke Valley Road 153791

Osterville house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$495

21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$378

Great rentals within 20 miles that match your search

40 Ploughed Neck Rd

East Sandwich house

4 bedrooms / 3 bathrooms / sleeps 8

“Seaside home with all the amenities!” We had a fantastic stay at this beautiful, spacious home! The location is superb -- just a short walk to gorgeous East Sandwich Beach, a quick drive to historic Sandwich village, and easy access to Rt 6 and the rest of the Cape. The house has everything a family needs for a vacation on Cape Cod -- gourmet kitchen, two decks, a hot tub, outdoor shower, and plenty of cozy spots to curl up with a good book. The owners were very helpful and made us feel right at home. We can't wait to go back!

Price per night from

$466

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

4 bedrooms / 1 bathroom / sleeps 8

Price per night from

$584

Walk to Beach; 4 bedroom, 4 ba, Cape Cod Farmhouse

West Harwich house

5 bedrooms / 4 bathrooms / sleeps 8

“Delightful” From beginning to end, this was the absolute perfect place to stay on our Cape Cod adventure. The house was about as charming as you could get. We had 12 of us amazingly fit, with the rooms being so spacious. There were nooks and crannies with the cutest little details, book shelves for readers, games, a wonderful outdoor shower... Cindy and Harry have really put some thought and loving care into maintaining this beautiful house. We had family staying at several other locations and every night they all ended up here, usually around the fire pit. It's just a warm and friendly place to be. I must mention the 2 sheep that were on the property... adorable!! A nice walk to the beach and stores but really, at the end of the day, we just loved hanging out at the house.

Price per night from

$700

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

5 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$582

Cape Cod 2 BR Condo at the Beach August 5-12 !

Dennis Port hotel apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$250

Timeshare rental Cove at Yarmouth, Cape Cod, MA

West Yarmouth hotel apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$187

Crows Nest @ Captain Alexander's Hideaway

West Harwich house

2 bedrooms / 1 bathroom / sleeps 4

“Great place to stay and play” A great place to stay for a vacation on Cape Cod. The rooms were comfortable and of good size. There was a relaxing atmosphere and all the comforts of home. Plenty of games and videos for adults and kids and a large screen TV. Parking was ample and easy to come and go. The kitchen was more than expected. The back yard and spacious rear deck and furnishings made outdoor meals and barbecuing a pleasure. I especially liked the covered outdoor shower (with hotwater) to wash away beach sand and ocean salt. Speaking of ocean salt, the beach is just a short walk away.

Price per night from

$117

Short Stroll To Sea Street Beach In Dennisport

Dennis Port cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Cottage was even cuter than the picture!” We were pleasantly surprised that our little cottage was even cuter than we expected. It was well equipped for our week long stay and so close to the beach. Dennisport had wonderful restaurants-Scargo had a gluten free menu for a perfect birthday dinner. The cottage was a great location to explore other areas of the cape. We took the fast ferry from Hyannis to Nantucket one day. We would definitely like to stay at this cottage nestled in a group of 5 cottages encircled with a little white picket fence again. Thanks for sharing your adorable , freshly updated cottage with us.

Responds fast! avg. 1 hour 3 minutes

Price per night from

$257

AFFORDABLE WATER VIEW Cape Cod

Pocasset cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

Expansive Cape Get Away - The Grey Whale Awaits!

Cotuit house

7 bedrooms / 5 bathrooms / sleeps 24

Price per night from

$817

Charming Cape Cod Cottage/ Walk to Beach/Canal

Sandwich house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$55

Great Location, Beautiful Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$584

WATERFRONT 3 Bedroom Beach Home

Onset house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$584

Walk to Multiple Beaches and Downtown

Wareham house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$250

Ocean, lake, harbor & parkview Vineyard cottage w/AC

Oak Bluffs cottage

6 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 6 minutes

Price per night from

$584

Minutes to Menauhant Beach - Newly Furnished

Falmouth house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$438

New Cape House Steps to the Beach in East Falmouth

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$438

Private Home with 2 MBRs on Private Road and Beach

Barnstable house

5 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$584

Cape Cod Fun & Sun WIFI Central A/C

Dennis Port cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$226

Private sandy beach - Ocean view 4 BR house

Sandwich house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 30 minutes

Price per night from

$397

Immaculate SeaView Beach House in S.Yarmouth

South Yarmouth house

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 29 minutes

Price per night from

$582

Waterfront-Martha's Vineyard

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$409

Captain's Quarters @ Captain Alexander's Hideaway

West Harwich house

/ 1 bathroom / sleeps 2

Price per night from

$170

Two Wing Cottage - escape with family and friends

Harwich Port cottage

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,458

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

5 bedrooms / 5 bathrooms / sleeps 19

Price per night from

$3,499

Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town

Vineyard Haven house

2 bedrooms / 1 bathroom / sleeps 4

“great stay in Vineyard Haven” We enjoyed staying in David's guest house. It was clean, well situated (a short walk from downtown Vineyard Haven), and made for a relaxing few days on the Vineyard. David was easy to reach and very responsive to any of our needs. I would highly recommend you stay at the guesthouse.

Price per night from

$245

Waterfront home - Spectacular Sunsets

Bourne house

4 bedrooms / 2 bathrooms / sleeps 9

“Peace & Tranquility” I have stayed here 4+ times, and I come home relaxed and rejuvenated. It's centrally located in the middle of the western cape, the sunsets are perfect, we usually have meals out on the expansive deck, we bring our kayaks, watch the shipping entering the canal, walk/run/bike the canal path(both sides), cook or grill fresh seafood from local stores, enjoy the wine tastings at the Belfry, jump over to the vineyard for the day, and did I mention the sunsets? The home is roomy, light and airy, plenty of parking, just perfect for us.

Price per night from

$642

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

Responds fast! avg. 1 hour 42 minutes

Price per night from

$321

Olde Sea Captains House great for family reunions. 7/10th of a mile to the beach

Dennis Port house

6 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$747

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

2 bedrooms / 2 bathrooms / sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

Price per night from

$269

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 29 minutes

Price per night from

$350

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$321

Viewing 38 of 1,101
rentals in Osterville

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