Chatham Vacation Rentals & Apartments with Swimming Pool - 56 Rentals Available.
56 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
$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
$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
$992.00
from $992.00 / 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
$807.00
from $807.00 / 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
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 19.3 miles to include more rentals
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
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
$1,031.00
from $1,031.00 / 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
$150.00
from $150.00 / night
#456:Large pool, fenced-in yard, fire pit, foosball table, & close to Great Pond
Eastham House - 11.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$213.00
from $213.00 / 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
#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
$653.00
from $653.00 / 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 10 10
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$300.00
from $300.00 / night
#908: Water Views from Multiple Decks, Private Pool, Access to Grand Cove!
West Dennis House - 10.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$374.00
from $374.00 / 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
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
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
$186.00
from $186.00 / night
360 Windjammer Lane 146863
Eastham House - 8.5 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$400.00
from $400.00 / 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
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
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
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
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
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
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
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
$893.00
from $893.00 / 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 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
- 1 night min
- Swimming pool
- Child friendly
$2,550.00
from $2,550.00 / 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
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
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
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
$313.00
from $313.00 / 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
$539.00
from $539.00 / 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
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
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