Chatham Vacation Rentals & Apartments with Swimming Pool - 54 Rentals Available.
54 Vacation rentals
Filters applied: Swimming pool
300 Stage Neck Road
Chatham House
- 8 bedrooms 8
- 11 bathrooms
- sleeps 16 16
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$5,428.00
from $5,428.00 / 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
$1,429.00
from $1,429.00 / 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
$1,786.00
from $1,786.00 / 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
$1,020.00
from $1,020.00 / 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
$1,438.00
from $1,438.00 / 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
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
$1,325.00
from $1,325.00 / night
Your search has been expanded 18 miles to include more rentals
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
$786.00
from $786.00 / 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
$85.00
from $85.00 / 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
$514.00
from $514.00 / 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
$1,357.00
from $1,357.00 / 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
$822.00
from $822.00 / 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
$440.00
from $440.00 / 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
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
$697.00
from $697.00 / night
Thumpertown - 3790
Eastham Cottage - 11.3 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$186.00
from $186.00 / 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
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
$213.00
from $213.00 / night
102 Constance Avenue
Yarmouth House - 13.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$285.00
from $285.00 / 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
$360.00
from $360.00 / 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
$215.00
from $215.00 / night
Quaint cottage colony home-Just 75 feet to Sea Street Beach
Dennis Port House - 9.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$79.00
from $79.00 / night
Captain Nickerson Lane 18
South Dennis House - 10.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Three bedroom home sleeping 9 with private swimming pool
South Dennis House - 9.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / 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
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
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
$2,000.00
from $2,000.00 / 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
Responds fast! Avg. 1 hour 56 minutes
$299.00
from $299.00 / night
#317: The Captain’s House: Private Pool, Tennis Courts, Game Room, Dog friendly
Wellfleet House - 18 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 56 minutes
$325.00
from $325.00 / night
Modern Harwich Home with Heated Salt Water Pool: 001-HR
Harwich House - 7.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$825.00
from $825.00 / 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
Kingsbury - 3798
Eastham House - 11 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$272.00
from $272.00 / night
#908 - 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
Responds fast! Avg. 1 hour 56 minutes
$442.00
from $442.00 / night
79 Chase Ave - 2 Bedroom
Dennis Port Condo - 8.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$100.00
from $100.00 / night
Nauset Light - 3948
Eastham House - 12 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
Resplendent in South Orleans, Heated Pool, Sleeps up to 12; 184-O
Orleans House - 3.9 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$807.00
from $807.00 / night
Studio condo unit, with shared pool and steps from the beach!
Dennis Port Studio - 9.6 miles away
- Studio -1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$72.00
from $72.00 / 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
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
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