Chatham Vacation Rentals & Apartments with Swimming Pool - 59 Rentals Available.
59 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
$2,000.00
from $2,000.00 / 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
$2,142.00
from $2,142.00 / 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
$1,028.00
from $1,028.00 / 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
Just Built, 5-bedroom Chatham Beauty w/heated Pool, Overlooks Cranberry Bog 30-C
Chatham House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$702.00
from $702.00 / 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
$719.00
from $719.00 / night
8175 Goumas
Chatham House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 11 11
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$857.00
from $857.00 / night
12 Wapoos Trail
Chatham House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,214.00
from $1,214.00 / 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
$857.00
from $857.00 / 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
$493.00
from $493.00 / night
Your search has been expanded 18 miles to include more rentals
OCEANFRONT HOME Completely Rebuilt Brand New
West Yarmouth House - 14.3 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$1,031.00
from $1,031.00 / 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
$668.00
from $668.00 / 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
$334.00
from $334.00 / 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
$676.00
from $676.00 / 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
$1,835.00
from $1,835.00 / 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
$481.00
from $481.00 / 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
$1,002.00
from $1,002.00 / 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
$385.00
from $385.00 / 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
$1,352.00
from $1,352.00 / 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
$899.00
from $899.00 / 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
$565.00
from $565.00 / night
Salt Water Pool, Steps to Private Beach, Exclusive Quiet Neighborhood :023-H
West Harwich House - 7.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$361.00
from $361.00 / 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 17 17
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$776.00
from $776.00 / 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
$407.00
from $407.00 / 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
$735.00
from $735.00 / 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
$668.00
from $668.00 / night
Two Cottages with a Brand New Pool, ½ mile to Private Beach: 048-B
Brewster House - 7.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$253.00
from $253.00 / 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
$303.00
from $303.00 / 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
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
$565.00
from $565.00 / 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
$1,772.00
from $1,772.00 / 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
$862.00
from $862.00 / 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
$437.00
from $437.00 / 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
Kingsbury - 3798
Eastham House - 11 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$286.00
from $286.00 / 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
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
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
$93.00
from $93.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.