Osterville Vacation Rentals & Homes - 875 Rentals Available
875 Vacation rentals

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
from $200.00 / night

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
from $412.00 / night
Your search has been expanded 19.6 miles to include more rentals

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
$573.00
from $573.00 / night

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
$246.00
from $246.00 / night

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
$573.00
from $573.00 / night
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
from $430.00 / night
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
from $573.00 / night
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
$221.00
from $221.00 / night
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
from $401.00 / night
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
from $458.00 / night
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
$221.00
from $221.00 / night
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
from $172.00 / night
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
from $572.00 / night
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
from $516.00 / night
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
from $1,064.00 / night
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
$430.00
from $430.00 / night
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
$916.00
from $916.00 / night
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
$390.00
from $390.00 / night
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
$572.00
from $572.00 / night
16636: Newly Renovated Pond Front Home, Dog Friendly w/ Fenced Yard, Game Room!
South Chatham House - 19.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$230.00
from $230.00 / night
19916: Waterfront fun awaits at this updated antique home! Dog friendly!
West Dennis House - 11.3 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 16 16
- min stay varies
- Child friendly
- Pet friendly
$340.00
from $340.00 / night
19905: Fully Renovated, Mahogany Deck w/ Granite Bar, Walk to Scargo Lake!
Dennis House - 13.2 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$159.00
from $159.00 / night
20004: Deeded Rights to Dinah's & Follins Ponds, Kayaks/SUP Boards, Dog Friendly
South Yarmouth House - 11.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$68.00
from $68.00 / night
19926: Short Walk to Nantucket Sound Beach w/ Views of the Park!
Dennis Port House - 13.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$120.00
from $120.00 / night
17731: Beautifully Renovated in Harwich Center, .3 Mile to Bike Trail, < 2 Miles
Harwich House - 16.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$129.00
from $129.00 / night
16614: Walk to Oyster River, minutes to downtown & beaches! Dog friendly!
South Harwich House - 16.6 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$210.00
from $210.00 / night
16667: Waterfront on Mill Pond w/ 70 Ft of Shoreline, Direct Pond Access & Unobs
South Chatham House - 19.5 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
17727: Harbor View, 1 Min Walk to Beach, Patio, Gas Fireplace, & Central A/C!
Harwich Port House - 17.3 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$268.00
from $268.00 / night
20007: Beachfront on Nantucket Sound w/ Unobstructed Ocean Views!
South Yarmouth House - 8.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$247.00
from $247.00 / night
17730: Walk 300 Yards to Beautiful Sandy Nantucket Sound Beach from this Picture
Harwich Port House - 17.9 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Air conditioning
$360.00
from $360.00 / night
18817 - A true beach house, with a lookout tower, located on the bay.
Brewster House - 19.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$393.00
from $393.00 / night
19923: Modern & Comfortable Home w/ Sun Room, Spacious Back Deck, Central A/C!
South Dennis House - 13.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$121.00
from $121.00 / night
16606: GAME ROOM! Large backyard w/deck. 10-min walk to Nantucket Sound!
South Chatham House - 18.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Pet friendly
$182.00
from $182.00 / night
20011: Luxurious Home & Location! Walk to Bass River Beach & Boat Ramp, Game Roo
South Yarmouth House - 9.7 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Air conditioning
$118.00
from $118.00 / night
18803: Newly Furnished, Huge Deck, Outdoor Shower, Private Yard, Near Beaches, D
Brewster House - 17 miles away
- 4 bedrooms 4
- 1 bathroom
- sleeps 8 8
- min stay varies
- Child friendly
- Pet friendly
$164.00
from $164.00 / night
16622: Private, Newly Renovated, Modern, Deeded Pond Access, Walk to Main Street
South Chatham House - 19.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Air conditioning
$224.00
from $224.00 / night
18818: Private Home in Quiet Neighborhood w/ Spacious Yard, Updated Appliances,
Brewster House - 19 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$91.00
from $91.00 / night
19927: Short Walk to Nantucket Sound Beach w/ Views of the Park!
Dennis Port House - 13.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$120.00
from $120.00 / night
17728: 1 Mile to Nantucket Sound Beach, Beautifully Updated, Great Outdoor Space
Harwich Port House - 17.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
- Air conditioning
$200.00
from $200.00 / night
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