Hotels with a Pool in Chatham

October 2026
November 2026

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This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Hotels with a Pool in Chatham

1. Greyfinch Chatham Inn

Greyfinch Chatham Inn
Chatham
  • Pool loungers
  • Near the beach
$169
$230 total
includes taxes & fees
Oct 18 - Oct 19
Greyfinch Chatham Inn

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Near the beach
$220
$252 total
includes taxes & fees
Oct 7 - Oct 8
Chatham Seafarer Inn

3. Chatham Bars Inn

Chatham Bars Inn
Chatham
  • On private beach
  • Full-service spa
$451
$516 total
includes taxes & fees
Oct 12 - Oct 13
Chatham Bars Inn

4. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Outdoor pool
  • Hot tub
$242
$276 total
includes taxes & fees
Sep 22 - Sep 23
Pleasant Bay Village Resort

5. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
  • Pool loungers
  • Near the beach
$396
$497 total
includes taxes & fees
Sep 21 - Sep 22
Chatham Wayside Inn

6. The Chatham Motel

The Chatham Motel
Chatham
  • Near the beach
$186
$213 total
includes taxes & fees
Oct 18 - Oct 19
The Chatham Motel

7. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
Orleans
  • Pool loungers
  • Near the beach
$104
$119 total
includes taxes & fees
Oct 5 - Oct 6
Olde Tavern Motel And Inn

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
  • Near the beach
$151
$173 total
includes taxes & fees
Sep 20 - Sep 21
Handkerchief Shoals Inn

9. Skaket Beach Motel

Skaket Beach Motel
Orleans
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Air conditioning
  • Laundry facilities
$130
$149 total
includes taxes & fees
Oct 12 - Oct 13
Skaket Beach Motel

10. The Villages at Ocean Edge

The Villages at Ocean Edge
Brewster
  • 3 outdoor pools
  • 2 indoor pools
  • 3 poolside bars
  • Children's pool
  • On private beach
  • Hot tub
$152
$220 total
includes taxes & fees
Oct 4 - Oct 5
The Villages at Ocean Edge

11. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
Dennis Port
  • Outdoor pool
  • Near the beach
$98
$112 total
includes taxes & fees
Sep 22 - Sep 23
Dennis Port Surf Club (Boutique Hotel)

12. Blue Rock Resort

Blue Rock Resort
South Yarmouth
  • Pool loungers
  • On private beach
$109
$126 total
includes taxes & fees
Sep 20 - Sep 21
Blue Rock Resort

13. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • 2 poolside bars
  • Pool loungers
  • On private beach
  • 2 hot tubs
$443
$542 total
includes taxes & fees
Oct 18 - Oct 19
Wequassett Resort and Golf Club

14. A Beach Breeze Inn

A Beach Breeze Inn
West Harwich
  • Pool loungers
  • Near the beach
$129
$148 total
includes taxes & fees
Oct 12 - Oct 13
A Beach Breeze Inn

15. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
  • Near the beach
$106
$121 total
includes taxes & fees
Oct 1 - Oct 2
Rodeway Inn Orleans - Cape Cod

16. The Escape Inn

The Escape Inn
Bass River
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Air conditioning
  • 24/7 front desk
$94
$107 total
includes taxes & fees
Oct 1 - Oct 2
The Escape Inn

17. The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort
Dennis Port
  • 2 outdoor pools
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
  • 2 hot tubs
$96
$118 total
includes taxes & fees
Sep 27 - Sep 28
The Corsair & Cross Rip Oceanfront Resort

18. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
Dennis Port
  • Pool loungers
  • Near the beach
$107
$123 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Hill Inn & Suites

19. Love Farms Lodge

Love Farms Lodge
West Dennis
  • Pool loungers
$122
$150 total
includes taxes & fees
Sep 28 - Sep 29
Love Farms Lodge

20. Charm on Main by Ocean Edge

Charm on Main by Ocean Edge
Sea Pines
  • Pool loungers
  • Near private beach
  • Full-service spa
$211
$241 total
includes taxes & fees
Sep 21 - Sep 22
Charm on Main by Ocean Edge
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Discover your perfect hotel with a pool in Chatham

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Top landmarks in Chatham

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)
If want to top up your tan, you might want to head out to Chatham Lighthouse Beach, located 1.2 mi (2 km) from central Chatham. Enjoy the sunset by the shore at Hardings Beach, Ridgevale Beach, and Red River Beach.
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A lighthouse with a glass enclosure and metal railing, set against a partly cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)
If you're planning a bit of sightseeing during your trip, head to Chatham Lighthouse— just one of the landmarks located 1 mi (1.6 km) from central Chatham. Why not take a stroll along the beaches and watch the sunset while you're here?
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A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)
Chatham Fish Pier is 0.7 mi (1.1 km) from central Chatham, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?
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A windmill, a boat, and a beach.

Chatham Windmill

9.2/10 (38 reviews)
Chatham Windmill is 0.5 mi (0.7 km) from central Chatham, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?
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A beach at sunset with the sun low on the horizon, casting long shadows on the sand.
Photo by Janice Schlegel

Monomoy National Wildlife Refuge

9.8/10 (14 reviews)
Monomoy National Wildlife Refuge is 1.7 mi (2.8 km) from central Chatham, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?
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Ridgevale Beach

9.6/10 (21 reviews)
If being by the water is a major draw, Ridgevale Beach is a spot you might want to check out, located 2.4 mi (3.9 km) from central Chatham. If you want to continue walking by the waves, head to Hardings Beach and Cockle Cove Beach, both within a short walk.
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Cockle Cove Beach

9.0/10 (28 reviews)
Whether you want to hunt for sand dollars or smell the fresh air, Cockle Cove Beach is a spot you might want to check out, located 2.6 mi (4.3 km) from central Chatham. If you want to continue walking by the waves, head to Ridgevale Beach and Forest Beach, both within a short walk.
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Mayo House

8.0/10 (3 reviews)
If you're planning a bit of sightseeing during your trip, head to Mayo House— just one of the monuments in central Chatham. Why not take a stroll along the beaches and watch the sunset while you're here?
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About the destination

Chatham is a trendy spot known for its beaches. Learn about the local heritage of Chatham at landmarks like Chatham Lighthouse and Chatham Lighthouse Beach. A stop at other sights like Ridgevale Beach and Cape Cod Beaches will create memories.