Chatham Vacation Rentals & Apartments with Swimming Pool - 55 Rentals Available.
55 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
- Ask about pets
$2,285.00
from $2,285.00 / 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
$1,285.00
from $1,285.00 / 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
$714.00
from $714.00 / night
Spacious Custom Chatham Home Plus Guest House: 051-C
Chatham House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Child friendly
$1,360.00
from $1,360.00 / 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
$1,130.00
from $1,130.00 / 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
- Pet friendly
$977.00
from $977.00 / night
Chatham: Luxury Living, Brand New with Pool : 096-C
Chatham House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$662.00
from $662.00 / night
Your search has been expanded 18 miles to include more rentals
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
$2,142.00
from $2,142.00 / 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
Private resort, three homes, one property. Walk to the beach, new pool!
Eastham House - 12.4 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 18 18
- min stay varies
- Nearest beach 0.8 mi
- Swimming pool
- Child friendly
$1,145.00
from $1,145.00 / night
3 homes in 1, new pool, walk to beach. Great for multiple families!
Eastham House - 12.6 miles away
- 7 bedrooms 7
- 4 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$916.00
from $916.00 / night
61 Chase Ave
Dennis Port Apartment - 8.5 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / night
OCEANFRONT HOME Completely Rebuilt Brand New
West Yarmouth House - 14.3 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$1,260.00
from $1,260.00 / 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
$383.00
from $383.00 / night
Orleans: 2+ Acres, Pool, Comfortable Luxury, Steps to Beach: 030-OC
Orleans House - 5.7 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$844.00
from $844.00 / night
Expansive Luxury Home with Pool, One Minute Walk to Private Beach: 050-O
Orleans House - 5.6 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$1,202.00
from $1,202.00 / 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
$1,744.00
from $1,744.00 / night
Private Orleans resort-style compound w/heated pool & spa and fire pit: 023-O
Orleans House - 6.9 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$1,147.00
from $1,147.00 / night
Brand New Custom Brewster Home with Pool, 4 Min Walk to Private Beach 105-BF
Brewster House - 7.9 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$662.00
from $662.00 / 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
$250.00
from $250.00 / 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
$826.00
from $826.00 / night
Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 417-B
Brewster House - 9.8 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 20 20
- min stay varies
- Swimming pool
- Child friendly
$1,233.00
from $1,233.00 / night
Updated East Orleans 6 Bed with Heated pool: 004-O
East Orleans House - 7 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$492.00
from $492.00 / 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
$1,797.00
from $1,797.00 / night
Magnificent Orleans Estate w/Pool, Tennis, Assoc. Dock & Beach on Pleasant Bay
Orleans House - 4.4 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
$1,022.00
from $1,022.00 / night
Spacious Modern Home with huge pool! : 011-Y
Yarmouth Port House - 13.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$421.00
from $421.00 / night
Private Orleans resort w/water views, heated pool/spa; sleeps 16 (linens) 009-O
Orleans House - 8.3 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 15 15
- min stay varies
- Swimming pool
- Child friendly
$1,118.00
from $1,118.00 / night
Captivating in South Orleans, New, Spacious, Pristine with Heated Pool: 005-O
South Orleans House - 4.9 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$692.00
from $692.00 / night
Superbly Remodeled Captain’s Home Less than Two Miles from Nauset Beach: 100-OB
Orleans House - 6.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$511.00
from $511.00 / 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
$857.00
from $857.00 / night
Upscale, Resort-like, Heated Pool/Spa, Sleeps 14: 002-H
West Harwich House - 7.4 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$838.00
from $838.00 / night
New to 2020! In ground pool sleeping 10 on the North Side!!!
Dennis House - 11.3 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$285.00
from $285.00 / night
Great cottage close to Nauset Beach, (linens included): 040-O
Orleans House - 7.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
$437.00
from $437.00 / night
Elegantly Renovated, Walk 3 Min. to Beach -- 113-B
Brewster House - 7.8 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 13 13
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$649.00
from $649.00 / 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
$348.00
from $348.00 / night
Orleans Oasis on Pleasant Bay, estate w/2 homes & heated pool; sleeps 14: 137-O
Orleans House - 4.8 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$1,130.00
from $1,130.00 / night
Private, Updated 4+ Acre Family Compound, Pool, Water Views, Sunsets: 071-D
Dennis House - 11.2 miles away
- 8 bedrooms 8
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$777.00
from $777.00 / night
Luxurious Orleans Home w/Private Salt Pool: 012-O
Orleans House - 4.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$600.00
from $600.00 / night
Spacious and Gracious with Pool, Spa, Near Beaches, Bike Paths; 011-B
Brewster House - 7.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
$462.00
from $462.00 / 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
$668.00
from $668.00 / night
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