Find Hotels with a Pool in Chatham, MA
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Sep 1 - Sep 2Tomorrow
Sep 2 - Sep 3This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13Our top choices for Chatham hotels with a pool
1. Greyfinch Chatham Inn
Greyfinch Chatham InnChatham
- Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
$204 nightly
$233 total
Sep 27 - Sep 28
Total with taxes and fees
2. Chatham Seafarer Inn
Chatham Seafarer InnChatham
- Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$211 nightly
$242 total
Sep 17 - Sep 18
Total with taxes and fees
3. Chatham Wayside Inn
Chatham Wayside InnChatham
- Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
$337 nightly
$386 total
Sep 29 - Sep 30
Total with taxes and fees
4. Pleasant Bay Village Resort
Pleasant Bay Village ResortChatham
- Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$237 nightly
$271 total
Sep 22 - Sep 23
Total with taxes and fees
5. Chatham Bars Inn
Chatham Bars InnChatham
- Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
$808 nightly
$924 total
Sep 29 - Sep 30
Total with taxes and fees
6. The Chatham Motel
The Chatham MotelChatham
- Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
$234 nightly
$268 total
Sep 2 - Sep 3
Total with taxes and fees
7. Olde Tavern Motel And Inn
Olde Tavern Motel And InnOrleans
- Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.
$97 nightly
$111 total
Sep 3 - Sep 4
Total with taxes and fees
8. Dennis Port Surf Club (Boutique Hotel)
Dennis Port Surf Club (Boutique Hotel)Dennis Port
- Seasonal outdoor pool offers refreshing oceanside swims after coastal adventures.
$99 nightly
$114 total
Sep 2 - Sep 3
Total with taxes and fees
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Top Chatham Hotel Reviews
The Villages at Ocean Edge
10/10 Excellent
"Okokokok"
Cape Sands Inn
10/10 Excellent
"Great spot for the Price will go again"
Holiday Hill Inn & Suites
10/10 Excellent
"Onky complaint is they have these small trees in the parking lot."
Bayside Resort Hotel
10/10 Excellent
"We had a wonderful overnight stay. The room was very clean and the staff was very helpful. Will definitely stay here again."
Queen Anne Inn
8/10 Good
"7/10 — Charming property with room for improvement We stayed for two nights this past weekend and overall had a pleasant stay. We were in the back cottage, and the room itself was totally fine. I especially liked the hardwood floors, and we had no major concerns with the room during our stay. The bathroom could use some updating, but everything was functional. The main building has a cute, eclectic New England feel, with some really charming sitting areas and common spaces. There’s definitely a lot of character to the property, and with a few updates and a little more attention to the grounds, I think it could be a really lovely place. One area that stood out was the upkeep of the outdoor spaces. There were tables and chairs with quite a few fallen leaves sitting on them throughout the weekend, which made the outdoor areas feel a bit less inviting than they could have been. A little more regular maintenance would make a noticeable difference. The front desk receptionist was wonderful. She was very friendly and checked in with us a couple of times throughout the weekend to make sure everything was going well and that we didn’t need anything, which we really appreciated. Overall, we had a good stay and everything went smoothly. The property has a lot of charm and potential, and I think some updates to the bathrooms and a bit more attention to the outdoor grounds could really elevate the experience."
Holiday Inn Express Hyannis Cape Cod by IHG
10/10 Excellent
"Everything was clean, breakfast great, I loved that I was able to be with my furry child!"
Pleasant Bay Village Resort
10/10 Excellent
"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and the turn down service was excellent. They have a great pool and hot tub. They also have a koi fish pond that is beautiful. We especially enjoyed the outdoor tables in the courtyards of each area. We were able to bring back lobster rolls from the fish market and enjoy a nice al fresco dinner. We then ran into the cleaning who offered to take our garbage from us, which was so helpful as it prevented us from stinking up the room. I would definitely recommend this resort to anyone staying n Chatham. Well worth it!"
Freebird Motor Lodge by Reverie Boutique Collection
10/10 Excellent
"Clean and convenient"
Uncommoner Hotel by Reverie Boutique Collection
10/10 Excellent
"Great location! Clean rooms, 2 great pools!"
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