Osterville 2-bedroom Vacation Rentals, Homes & More - 1743 Rentals Available.
1,743 Vacation rentals
Filters applied: 2+ Bedrooms
225 Wianno Circle
Osterville House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$386.00
from $386.00 / night
306 West Bay Road
Osterville House
- 3 bedrooms 3
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Ask about children
- Pet friendly
$929.00
from $929.00 / night
206 East Bay Road
Osterville House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$1,214.00
from $1,214.00 / night
246 Wianno Circle
Osterville House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 9 9
- 1 night min
- Ask about children
- Ask about pets
$428.00
from $428.00 / night
146 Hollingsworth Road
Osterville House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$357.00
from $357.00 / night
405 Sea View Avenue
Osterville House
- 10 bedrooms 10
- 12 bathrooms
- sleeps 22 22
- 1 night min
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
77 Robbins Street
Osterville House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 1 night min
- Ask about children
- Ask about pets
$357.00
from $357.00 / night
94 Waterfield Road
Osterville House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$271.00
from $271.00 / night
86 Leonard Road
Osterville House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Ask about pets
$1,072.00
from $1,072.00 / night
24 South Street
Osterville House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$400.00
from $400.00 / night
17 Indian Trail
Osterville House
- 9 bedrooms 9
- 9 bathrooms
- sleeps 1 1
- 1 night min
- Ask about children
- Ask about pets
$3,571.00
from $3,571.00 / night
92 Concord Lane
Osterville House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$250.00
from $250.00 / night
STUNNING ESTATE LIKE PROPERTY NEAR VILLAGE/BEACH! 96974
Osterville House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$415.00
from $415.00 / night
466 Parker Road
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Pet friendly
$257.00
from $257.00 / night
21 Cockachoisett Lane
Osterville House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$457.00
from $457.00 / night
101 Carriage Road
Osterville House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$3,571.00
from $3,571.00 / night
48 Pine Lane
Osterville House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$414.00
from $414.00 / night
26 Cedar Lane
Osterville House
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$571.00
from $571.00 / night
31 Eel River Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Ask about children
- Ask about pets
$571.00
from $571.00 / night
14 Indian Trail
Osterville House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$1,428.00
from $1,428.00 / night
439 Sea View Avenue
Osterville House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,571.00
from $2,571.00 / night
31 Parker Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$500.00
from $500.00 / night
83 Bunker Hill Road
Osterville House
- 5 bedrooms 5
- 7 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,285.00
from $1,285.00 / night
933 Main Street, #E
Osterville House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 1 night min
- Ask about children
- Ask about pets
$185.00
from $185.00 / night
71 Sand Point Road
Osterville House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,857.00
from $2,857.00 / night
77 Spice Lane
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$428.00
from $428.00 / night
12 Cockachoiset Lane
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Pet friendly
$614.00
from $614.00 / night
44 Sunset Lane
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Pet friendly
$357.00
from $357.00 / night
Remodeled GEM in Osterville with BEACH PASS!! 134586
Osterville House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$1,496.00
from $1,496.00 / night
979 Sea View Avenue
Osterville House
- 11 bedrooms 11
- 8 bathrooms
- sleeps 20 20
- 1 night min
- Ask about children
- Ask about pets
$1,785.00
from $1,785.00 / night
271 Eel River Road
Osterville House
- 8 bedrooms 8
- 8 bathrooms
- sleeps 20 20
- 1 night min
- Ask about children
- Ask about pets
$2,428.00
from $2,428.00 / night
PRIME SUMMER WEEK IN JULY STILL OPEN!! 121868
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$222.00
from $222.00 / night
236 Smoke Valley Road, #B
Osterville House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 5 5
- 1 night min
- Ask about children
- Ask about pets
$585.00
from $585.00 / night
87 Seapuit Road
Osterville House
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$857.00
from $857.00 / night
260 Wianno Avenue
Osterville House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Ask about children
- Pet friendly
$642.00
from $642.00 / night
49 Sylvan Lane
Osterville House
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 1 night min
- Ask about children
- Ask about pets
$357.00
from $357.00 / night
554 Wianno Avenue
Osterville House
- 12 bedrooms 12
- 8 bathrooms
- sleeps 15 15
- 1 night min
- Ask about children
- Ask about pets
$1,285.00
from $1,285.00 / night
154 Scudder Road
Osterville House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$642.00
from $642.00 / night
344 Bridge Street
Osterville House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 9 9
- 1 night min
- Ask about children
- Ask about pets
$985.00
from $985.00 / night
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