A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Hotel Guide - Hotels with Pool in Chatham, Massachusetts

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with Pool

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Chatham hotels with a pool

1. Greyfinch Chatham Inn

Greyfinch Chatham Inn
Chatham
  • Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
€234
includes taxes & fees
27 Sept - 28 Sept
Greyfinch Chatham Inn

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
€229
includes taxes & fees
22 Sept - 23 Sept
Chatham Seafarer Inn

3. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
  • Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
€390
includes taxes & fees
30 Aug - 31 Aug
Chatham Wayside Inn

4. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Splash into holiday bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
€237
includes taxes & fees
22 Sept - 23 Sept
Pleasant Bay Village Resort

5. Chatham Bars Inn

Chatham Bars Inn
Chatham
  • Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
€643
includes taxes & fees
14 Sept - 15 Sept
Chatham Bars Inn

6. The Chatham Motel

The Chatham Motel
Chatham
  • Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
€270
includes taxes & fees
31 Aug - 1 Sept
The Chatham Motel

7. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
Orleans
  • Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.
€117
includes taxes & fees
1 Sept - 2 Sept
Olde Tavern Motel And Inn

8. The Villages at Ocean Edge

The Villages at Ocean Edge
Brewster
  • Dive into paradise with 7 amazing pools, each offering a different vibe for every holiday mood.
€178
includes taxes & fees
20 Sept - 21 Sept
The Villages at Ocean Edge

9. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
€175
includes taxes & fees
14 Sept - 15 Sept
Handkerchief Shoals Inn

10. Skaket Beach Motel

Skaket Beach Motel
Orleans
  • Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.
€137
includes taxes & fees
15 Sept - 16 Sept
Skaket Beach Motel
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

Queen Anne Inn

Queen Anne Inn

10/10 Excellent
"We stayed at the Queen Anne Inn during our recent trip to Chatham and came away really impressed. The Inn has a wonderful old-Cape-Cod character. You can tell it's been a fixture in town for generations, and it's a nice change from the newer, more generic places nearby. The garden and grounds add a lot to the peaceful, unhurried feel of the place, and it's an easy walk into downtown Chatham for shopping and restaurants."
Parker 3-night trip
Posted less than an hour ago
Queen Anne Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"I love this property well maintained. Fun activities for kids and adults staff are very nice."
Myriam 1-night trip
Posted 1 hour ago
Margaritaville Resort Cape Cod
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Modern updated,comfortable room,nice indoor and outdoor pools, jacuzzi,firepit with seating area. Close to activities and beaches."
Christina 1-night trip
Posted 1 hour ago
Cape Sands Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Everything the whole place was nice, clean and quiet the breakfast room was well organized and packed I really enjoyed my stay good job from everyone there"
Angelica 3-night trip
Posted 2 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Great amenities, nice bonfire outside every night, great view of the salt marshes, and two beautiful pools. Very appetizing breakfast as well and nice staff. Everything we could have asked for at a great price."
Theodore 4-night trip
Posted 15 hours ago
Bayside Resort Hotel
The Villages at Ocean Edge

The Villages at Ocean Edge

10/10 Excellent
"Clean room and helpful staff. Would be great to have more of a coffee shop for grab and go items in the villa area"
Laura 1-night trip
Posted 15 hours ago
The Villages at Ocean Edge
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"Very clean, staff AWESOME. . Pool immaculate!! Location!!! Bathrooms dated but least of your worries. Best deal on the Cape. Only place I stay when visiting mid Cape!"
Andrew 4-night trip
Posted 18 hours ago
Holiday Hill Inn & Suites
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"I would highly recommend this hotel for Its location, amenities and comfortable rooms. It was a nice place"
Susan 2-night trip
Posted 22 hours ago
Hyannis Harbor Hotel
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

8/10 Good
"Petit déjeuner n’importe quoi"
Younes 4-night trip
Posted 2 days ago
The Mariner Resort Cape Cod by The Red Collection

Frequently asked questions

What are some accommodation options with pools in Chatham?
Chatham Bars Inn: Resort, 4-minute walk from Cape Cod Beaches. Features a private beach, a seasonal outdoor pool and a full-service spa. Chatham Wayside Inn: Hotel, 11-minute walk from Cape Cod Beaches. Offers daily, a seasonal outdoor pool and free self parking. The Chatham Motel: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Chatham?
Explore places such as Cape Cod Beaches while you're in Chatham. Make a point to visit attractions such as Chatham Lighthouse Beach and Chatham Railroad Museum. Visitors to Chatham speak highly of the natural attractions, including the beautiful beaches.
When is the best time to book a hotel with a pool in Chatham?
Taking the local weather in Chatham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 19°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chatham is 1362 mm.