Chatham Vacation Rentals & Apartments with Swimming Pool - 61 Rentals Available.
61 Vacation rentals
Filters applied: Swimming pool
166 Barcliff Avenue
Chatham House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Pet friendly
$2,000.00
from $2,000.00 / night
Waterfront 6 Bedroom with Pool and Private Dock
Chatham House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,715.00
from $1,715.00 / night
464 Shore Road
Chatham House
- 4 bedrooms 4
- 6 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,714.00
from $1,714.00 / night
103 Bellamy Lane
Chatham House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$928.00
from $928.00 / night
Spacious Custom Chatham Home Plus Guest House: 051-C
Chatham House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$1,284.00
from $1,284.00 / night
Chatham Resort Feel: Sleeps 16, Heated Pool/Spa, Renovated, Roomy, Upscale: 65-C
Chatham House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$1,002.00
from $1,002.00 / night
Updated Chatham Family Compound, Large Heated Pool, Walk to Town 489-C
Chatham House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$925.00
from $925.00 / night
48 Tilipi Run Street
Chatham House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$685.00
from $685.00 / night
324 Deer Meadow Lane
Chatham House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$928.00
from $928.00 / night
Your search has been expanded 19.3 miles to include more rentals
Whispering Pines - Cottage 13 126193
Eastham House - 9.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$228.00
from $228.00 / night
GORGEOUS Home with Pool and Central A/C 106854
Eastham House - 10.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$886.00
from $886.00 / night
5 Bedroom LUXURY HOME with inground HEATED POOL in Historic Barnstable Village
Barnstable House - 17.3 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Nearest beach 5 mi
- Swimming pool
- Ask about children
$572.00
from $572.00 / night
The Residences at TRADE WINDS w/Ocean Views! 135324
West Hyannisport Apartment - 19.3 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$358.00
from $358.00 / night
17 Sound View Road 130104
Harwich House - 3.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
Dog Friendly 4 Bedroom with Pool, 2 Min Walk to Beach
Eastham House - 12.3 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$229.00
from $229.00 / night
Kingsbury - 3798
Eastham House - 11 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$300.00
from $300.00 / night
58 Pleasant Street
South Dennis House - 10.6 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,785.00
from $1,785.00 / night
35 Old Duck Hole Road
Orleans House - 7 miles away
- 3 bedrooms 3
- 5 bathrooms
- sleeps 6 6
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,785.00
from $1,785.00 / night
14 Grayton Avenue
Hyannis Port House - 18 miles away
- 6 bedrooms 6
- 8 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$2,142.00
from $2,142.00 / night
Secluded with Private Pool, Pets Considered -181-B
Brewster House - 5.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$675.00
from $675.00 / night
Orleans Estate w/large heated pool, sleeps 24:39-O
Orleans House - 7.3 miles away
- 10 bedrooms 10
- 8 bathrooms
- sleeps 24 24
- min stay varies
- Swimming pool
- Child friendly
$1,902.00
from $1,902.00 / night
Updated, Spacious & Private, Sleeps 12 with Carriage House and Pool: 010-O
Orleans House - 8.2 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$514.00
from $514.00 / night
Private Saltwater Pool, 0.3 Miles to Beach, Central AC: 037-B
Brewster House - 7.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$462.00
from $462.00 / night
Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 417-B
Brewster House - 9.8 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 22 22
- min stay varies
- Swimming pool
- Child friendly
$1,480.00
from $1,480.00 / night
Modern, Magnificent & Private with Heated Pool; 032-B
Brewster House - 5.5 miles away
- 7 bedrooms 7
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$719.00
from $719.00 / night
Newly updated, heated pool, sleeps 12: 051-O
Orleans House - 7.1 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 13 13
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$822.00
from $822.00 / night
Oceanfront Estate with Pool, Spa, 6,600 sq ft of Sumptuous Summer Living: 047-O
Orleans House - 8 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$1,834.00
from $1,834.00 / night
Eight bedroom home sleeping 20 with private swimming pool
Harwich House - 3.9 miles away
- 8 bedrooms 8
- 2 bathrooms
- sleeps 20 20
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
NOW BOOKING FOR 2020! Gorgeous ocean views sleeping 8
Dennis Port House - 9.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
New to our inventory! Heritage Sands condo less than 500 feet to the beach!
Dennis Port Condo - 9.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Cape Cod cottage-Just 150 feet to Sea Street Beach
Dennis Port House - 9.1 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$225.00
from $225.00 / night
Two bedroom Heritage Sands condo-Less than 500 feet to shared/private beach
Dennis Port House - 9.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$229.00
from $229.00 / night
1 bedroom condo-just steps to the beach
Dennis Port House - 9.6 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$90.00
from $90.00 / night
Six bedroom sleeping 20 with private swimming pool
West Harwich House - 8 miles away
- 6 bedrooms 6
- 2 bathrooms
- sleeps 20 20
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
New to our inventory! Oceanfront Heritage Sands condo that sleeps 8.
Dennis Port House - 9.9 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$428.00
from $428.00 / night
Beautiful five bedroom home with private swimming pool
Dennis Port House - 8.4 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$429.00
from $429.00 / night
55 Barley Neck Rd 131073
East Orleans House - 6.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
#714: Massive luxury home, private pool and game room, walk to the beach!
Harwich Port House - 4.8 miles away
- 7 bedrooms 7
- 6 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
#447: Spacious family retreat with private pool! Close to Boat Meadow Beach!
Eastham House - 9.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$309.00
from $309.00 / night
#517 Endless Summer: Private pool, updated, minutes from Skaket Beach!
Orleans House - 7.7 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$299.00
from $299.00 / night
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