Holiday rentals with a pool in Chatham
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chatham
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chatham rentals with a pool
House rentals with a pool
Home in Dennis
4.89 out of 5 average rating, 27 reviewsWalk to the beach or sit poolside! Updated studio!
28 May – 4 Jun
Home in Orleans
4.88 out of 5 average rating, 17 reviews5-bedroom Cape with a pool and yard games.
26 Aug – 2 Sept
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
2–9 Jun
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
27 Sept – 4 Oct
Home in Harwich
4.81 out of 5 average rating, 31 reviewsFamilies: Enjoy Harwich, Pool, Large Hot Tub & AC!
16–23 May
Home in Eastham
5.0 out of 5 average rating, 9 reviewsModern Beach House w/ Heated Pool & Game Room!
18–25 Dec
Home in Yarmouth
4.89 out of 5 average rating, 36 reviewsWinslow Acres [heated] Pool Escape; pool May 15
26 Jan – 2 Feb
Home in North Truro
4.93 out of 5 average rating, 97 reviewsHeated Pool, Beach, Pets, ADA, 5 bath, EV Charge
6–13 Feb
Apartment rentals with a pool
Apartment in Brewster
4.84 out of 5 average rating, 31 reviewsGolf Course Views and Pools
22–29 May
Apartment in Dennis
4.83 out of 5 average rating, 65 reviewsComfy Cape Escape! Spacious, Cozy, Close to Beach!
13–20 Dec
Apartment in Brewster
4.87 out of 5 average rating, 23 reviewsStylish Ocean Edge Condo #TheCouplesNest
9–16 Nov
Apartment in Brewster
4.97 out of 5 average rating, 39 reviewsOcean Edge 2 Bed 2 Bath, Golf & Free Resort Access
12–19 Nov
Apartment in Brewster
4.83 out of 5 average rating, 18 reviewsOcean Edge: 2 bed/2 bath - Pool/Gym, Near Beaches
21–28 Jun
Apartment in Dennis
4.92 out of 5 average rating, 25 reviewsApril promo-Location-5 mins to beach-Pvt balcony
28 Jun – 5 Jul
Apartment in Brewster
5.0 out of 5 average rating, 52 reviewsOcean Edge Resort/Pool access/2bedroom-2bath Condo
10–17 Jan
Apartment in Dennis
4.83 out of 5 average rating, 18 reviews1BR 2nd Floor Condo with pool
3–10 Oct
Quick stats about holiday rentals with a pool in Chatham
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
200 reviews
Nightly prices starting at
£184 before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
- Martha's Vineyard Holiday rentals
- Cambridge Holiday rentals
- Nantucket Holiday rentals
- Salem Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Rentals with pools United States
- Rentals with pools Boston
- Rentals with pools Cape Cod
- Rentals with pools Martha's Vineyard
- Rentals with pools Massachusetts
- House rentals Chatham
- Fitness-friendly rentals Chatham
- Rentals with outdoor seating Chatham
- Rentals with beach access Chatham
- Waterfront rentals Chatham
- Rentals with a washing machine and dryer Chatham
- Pet-friendly rentals Chatham
- Family-friendly rentals Chatham
- Family-friendly rentals Chatham
- Rentals with a fireplace Chatham
- Rentals with breakfast Chatham
- Beachfront rentals Chatham
- Rentals with a firepit Chatham
- Rentals with a patio Chatham
- Rentals with a kayak Chatham
- Rentals with a hot tub Chatham
- Monthly Rentals Chatham
- Cottage rentals Chatham
- Rentals with lake access Chatham
- Rentals with pools Barnstable County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom