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

Hotels with Swimming 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 Swimming Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chatham hotels with a pool

A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.
An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.

1. 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.
P26,065
P29,832 total
includes taxes & fees
Oct 19 - Oct 20
Chatham Bars Inn
A swimming pool with lounge chairs and a white fence.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A garden with a pergola structure, a pathway, and a seating area.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

2. 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.
P11,222
P15,569 total
includes taxes & fees
Oct 29 - Oct 30
Chatham Wayside Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
A dining area with a glass table, chairs, and a vase with flowers.
A covered porch with a lattice design, a stone pathway, and a view of a garden.
A bedroom with a large bed, two side tables with lamps, a wooden nightstand, a wooden dresser, and a large window with a view of greenery.

3. 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.
P15,114
P17,297 total
includes taxes & fees
Oct 4 - Oct 5
Pleasant Bay Village Resort
Four sun loungers aligned along a poolside with a tiled floor.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.
A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

4. 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.
P10,066
P13,815 total
includes taxes & fees
Nov 1 - Nov 2
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
P12,145
P13,899 total
includes taxes & fees
Oct 7 - Oct 8
Chatham Seafarer Inn
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A dining area with tables set for two, overlooking a body of water with a sailboat.
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of the sea.
A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.

6. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
P25,327
P31,016 total
includes taxes & fees
Oct 19 - Oct 20
Wequassett Resort and Golf Club
A swimming pool with lounge chairs and a building in the background.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.
A blue door labeled "Office" with a small window and a mailbox.
A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
P8,374
P9,584 total
includes taxes & fees
Oct 4 - Oct 5
Handkerchief Shoals Inn
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

8. 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.
P6,203
P7,099 total
includes taxes & fees
Oct 4 - Oct 5
Olde Tavern Motel And Inn
An aerial view of a residential property with a swimming pool, a gazebo, and a well-maintained lawn.
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.
A sandy beach with gentle waves and a clear sky.
A kitchen with a white island, a fireplace, and a surfboard decoration.

9. Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod
Eastham
  • Dive into the inviting outdoor pool at this coastal retreat with comfortable sun loungers and peaceful gardens.
P7,447
P8,523 total
includes taxes & fees
Oct 4 - Oct 5
Eagle Wing Inn - Cape Cod
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

10. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
  • Splash into refreshing luxury with a clean, spacious pool perfect for sunny Cape Cod afternoons.
P6,539
P7,484 total
includes taxes & fees
Oct 4 - Oct 5
Rodeway Inn Orleans - Cape Cod
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

Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Clean, pool was great and heated !"
Melanie 4-night trip
Posted 4 hours ago
Riviera Beach Resort
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Nice hotel, restaurant with nice outdoor setting."
Monique 1-night trip
Posted 7 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Our room was beautiful and very clean! A little odd there was not any staff on site outside the hours of 3 pm - 8 pm but we do not stay at many small hotels so maybe this is normal. They did give us a phone number to call."
Kimberly 2-night trip
Posted 13 hours ago
Chatham Seafarer Inn
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Clean rooms and very helpful staff."
Louie 1-night trip
Posted 1 day ago
Hyannis Travel Inn
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Staff was excellent hotel clean"
Jerome 2-night trip
Posted 1 day ago
Cape Sands Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"Everything was exceptional!"
sheila 1-night trip
Posted 5 days ago
Pleasant Bay Village Resort
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"This place is so cute! When we first pulled up we were unsure because it looks like an old roadside motel. But it’s quickly apparent that it’s been beautifully updated with fresh paint and hanging plants. The driveway and parking lot are spotless as are the rooms. The decor in the rooms is updated and coastal. The staff was lovely. I would absolutely stay here again!"
Robert 4-night trip
Posted 7 days ago
Greyfinch Chatham Inn

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.

Explore a world of travel with Expedia