Top 20 Vacation Rentals in Osterville

271 Westwind Cir

Osterville House

3 bedrooms 3
4 bathrooms
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

$200.00

Excellent (2 reviews)

Inquire

from $200.00 / night

Inquire

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

Osterville House

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Child friendly
Air conditioning

$412.00

Book

from $412.00 / night

Book

WATERFRONT 3 Bedroom Beach Home

Onset House - 16 miles away

3 bedrooms 3
1 bathroom
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Nearest beach 1 mi
Child friendly

“we just wanted a relaxing vacation for my 85 year old mother. we couldnt have picked a more perfect home.. so beautiful sitting on the deck right on the water!! the house was very clean & so comfortable..would love to come back next year...”

- Review left on 08/01/2016

$573.00

Very Good (10 reviews)

Book

from $573.00 / night

Book

Walk to Multiple Beaches and Downtown

Wareham House - 15.8 miles away

3 bedrooms 3
1 bathroom
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Ask about children
Air conditioning

“I and my family of 7 have enjoyed staying here for our second, precious, annual summer getaway and we're looking forward to our third. It's just perfect. Clean, comfortable, air conditioned. Morning coffee watching the sun rise from the spacious deck...”

- Review left on 09/25/2015

$246.00

Very Good (10 reviews)

Book

from $246.00 / night

Book

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

Oak Bluffs Cottage - 14.9 miles away

6 bedrooms 6
3 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0.2 mi
Child friendly

Responds fast! Avg. 2 hours 15 minutes

“Great house and location! If you are looking for something with space, as well as the ability to walk to the bars and restaurants in Oak Bluffs, this is the house for you! Great location and great porch for those nights when you want to hang in....”

- Review left on 07/20/2014

$573.00

Excellent (3 reviews)

Book

from $573.00 / night

Book

New Cape House Steps to the Beach in East Falmouth

Falmouth House - 8.8 miles away

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Child friendly
Air conditioning

$430.00

Excellent (1 reviews)

Book

from $430.00 / night

Book

Private Home with 2 MBRs on Private Road and Beach

Barnstable House - 7.3 miles away

5 bedrooms 5
2 bathrooms
sleeps 8 8
6 nights min

Beach/lakeside relaxation
Ask about children
Air conditioning

$573.00

Book

from $573.00 / night

Book

Cape Cod Fun & Sun WIFI Central A/C

Dennis Port Cottage - 13 miles away

3 bedrooms 3
1 bathroom
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

“We rented this cottage without seeing it. It was really nice to be so pleasantly surprised, everything was perfect. Great location, close to beaches and all Dennis activities and restaurants. It was immaculate, the central air conditioning was...”

- Review left on 08/14/2016

$221.00

Excellent (8 reviews)

Book

from $221.00 / night

Book

Waterfront-Martha's Vineyard

Oak Bluffs House - 17.4 miles away

4 bedrooms 4
3 bathrooms
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Child friendly
Private garden

$401.00

Book

from $401.00 / night

Book

40 Ploughed Neck Rd

East Sandwich House - 8.4 miles away

4 bedrooms 4
3 bathrooms
sleeps 8 8
7 nights min

Child friendly
Air conditioning
Pet friendly

$458.00

Very Good (6 reviews)

Inquire

from $458.00 / night

Inquire

Spacious Air-Conditioned 3-Bedroom Close to Beach

South Yarmouth House - 9.2 miles away

3 bedrooms 3
1 bathroom
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Ask about children
Air conditioning

“This house was spacious, clean and affordable. It is an easy walk to the beach and is close to many attractions on the Cape. We plan on renting next year...”

- Review left on 08/08/2016

$221.00

Excellent (6 reviews)

Book

from $221.00 / night

Book

6 Earl Rd

East Sandwich House - 8.3 miles away

4 bedrooms 4
3 bathrooms
sleeps 6 6
7 nights min

Child friendly
Air conditioning
Private garden

$229.00

Inquire

from $229.00 / night

Inquire

3 Feake Ave

Sandwich House - 11.2 miles away

3 bedrooms 3
3 bathrooms
sleeps 9 9
7 nights min

Child friendly
Pet friendly

$172.00

Inquire

from $172.00 / night

Inquire

Sea & Keyes Beaches Paradise

Barnstable Villa - 5 miles away

5 bedrooms 5
4 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0.2 mi
Child friendly

Responds fast! Avg. 1 hour 29 minutes

$572.00

Excellent (1 reviews)

Book

from $572.00 / night

Book

Keyes Beach Retreat

Barnstable Villa - 5 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0.1 mi
Child friendly

Responds fast! Avg. 1 hour 29 minutes

$516.00

Excellent (1 reviews)

Book

from $516.00 / night

Book

OCEANFRONT HOME Completely Rebuilt Brand New

West Yarmouth House - 8.1 miles away

4 bedrooms 4
5 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

Responds fast! Avg. 3 hours 37 minutes

$1,064.00

Excellent (1 reviews)

Book

from $1,064.00 / night

Book

Minutes to Menauhant Beach - Newly Furnished

Falmouth House - 9.1 miles away

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Ask about children
Air conditioning

“Welcoming place. My family and I had had a good time staying at this place. Bedrooms were good size, layout of the kitchen and living room were nice along with the interior decoration. They had bikes which we took for a good ride to the beach about 2...”

- Review left on 09/14/2015

$430.00

Very Good (3 reviews)

Book

from $430.00 / night

Book

Magnificent Contemporary on Exclusive Point

Falmouth House - 14.4 miles away

3 bedrooms 3
4 bathrooms
sleeps 8 8
7 nights min

Beach/lakeside relaxation
Ask about children
Air conditioning

Responds fast! Avg. 25 minutes

“A wonderful fall get away! Wonderful location and a fabulous house with great amenities. Would definitely return for future vacations...”

- Review left on 10/27/2016

$916.00

Excellent (3 reviews)

Book

from $916.00 / night

Book

Private sandy beach - Ocean view 4 BR house

Sandwich House - 14.6 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0.6 mi
Ask about children

Responds fast! Avg. 1 hour 56 minutes

“A couple of friends and I decided to rent a house for New Years last minute. After searching for hours, we found, and secured, this house within three days. The owner is cool, very organized, and understanding. Along with that, the house was a great...”

- Review left on 01/19/2016

$390.00

Very Good (11 reviews)

Book

from $390.00 / night

Book

Immaculate SeaView Beach House in S.Yarmouth

South Yarmouth House - 8.9 miles away

5 bedrooms 5
2 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 0 mi
Child friendly

Responds fast! Avg. 1 hour 29 minutes

“The landlord Alex was very gracious. Everything we needed was provided which was very convenient since we traveled so far. The house was clean and spacious. Centrally located on the cape so we could travel easily in both directions. The beach is only...”

- Review left on 10/20/2016

$572.00

Excellent (13 reviews)

Book

from $572.00 / night

Book