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Find Hotels with a Pool in Chatham, MA

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Check availability on Chatham Hotels with a Pool

Tonight
Sep 8 - Sep 9
Tomorrow
Sep 9 - Sep 10
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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.
NT$5,605
NT$7,570 total
includes taxes & fees
Oct 1 - Oct 2
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.
NT$6,122
NT$7,007 total
includes taxes & fees
Oct 7 - Oct 8
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.
NT$11,329
NT$14,339 total
includes taxes & fees
Sep 29 - Sep 30
Chatham Wayside Inn

4. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
NT$7,619
NT$8,720 total
includes taxes & fees
Sep 22 - Sep 23
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.
NT$17,699
NT$20,256 total
includes taxes & fees
Sep 21 - Sep 22
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.
NT$8,875
NT$10,157 total
includes taxes & fees
Sep 9 - Sep 10
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.
NT$3,512
NT$4,020 total
includes taxes & fees
Oct 4 - Oct 5
Olde Tavern Motel And Inn

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
NT$4,217
NT$4,826 total
includes taxes & fees
Sep 14 - Sep 15
Handkerchief Shoals Inn

9. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
Dennis Port
  • Seasonal outdoor pool offers refreshing oceanside swims after coastal adventures.
NT$3,101
NT$3,549 total
includes taxes & fees
Sep 9 - Sep 10
Dennis Port Surf Club (Boutique Hotel)

10. 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 vacation mood.
NT$4,646
NT$6,762 total
includes taxes & fees
Sep 27 - Sep 28
The Villages at Ocean Edge
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

All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

8/10 Good
"Breakfast could be improved"
Ljupco 2-night trip
Posted 5 hours ago
All Seasons Resort, Trademark Collection by Wyndham
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Had a pleasant stay at the hotel!!! Cannot wait to come back !"
Myrielle 3-night trip
Posted 6 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Good location, helpful, friendly staff. The facility has been around awhile and could use a refresh, but it was very clean and well maintained. The grounds were well maintained and enjoyable to use. The pool was very clean The pool furniture was in good working order. The balcony was a nice plus. Would definitely book again."
Maureen 4-night trip
Posted 7 hours ago
Cape Sands Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Amazing stay very clean rooms and clean property, This beats all the competition around especially for the price! Easy check In and out. Amazing breakfast. VERY VERY Clean and fresh! one thing I am very picky about."
James 1-night trip
Posted 7 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"We went for the weekend. Staff was great answering all my questions. Bed was comfortable. Room was clean. Housekeeping came every day with fresh towels. Pool was taken care of very well. It sparkled.. close to the beach. Quiet. Just a short drive to activities and shops"
Mary 3-night trip
Posted 7 hours ago
Holiday Hill Inn & Suites
Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Clean."
Tucker 3-night trip
Posted 8 hours ago
Hyannis Harbor Hotel
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Great stay, room was clean. All the amenities are great especially the indoor and outdoor pool. Will continue to stay at this property and highly recommend for couples or family staying"
Desiree 2-night trip
Posted 8 hours ago
Bayside Resort Hotel
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Clean room, parking Great family trip"
Tatiana 3-night trip
Posted 9 hours ago
Margaritaville Resort Cape Cod
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"It would be cool to add a gym."
Nikolai 3-night trip
Posted 3 days ago
Freebird Motor Lodge by Reverie Boutique Collection

Frequently asked questions

What are some accommodations 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?
Spend some time experiencing the great outdoors at Chatham Lighthouse Beach and Ridgevale Beach. During your stay, check out sights such as Chatham Lighthouse, Cape Cod Beaches, and Cape Cod National Seashore. 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 into account the local weather in Chatham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches.

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