Hotels with a Pool in Chatham

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Hotels with a Pool in Chatham

Four sun loungers aligned along a poolside with a tiled floor.

A modern bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.

A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.

Greyfinch Chatham Inn

Chatham

Pool loungers
Near the beach

$178

$240 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with clear blue water, surrounded by blue and white lounge chairs.

A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

A house with a brick exterior, white exterior walls, and a front porch with white chairs.

A beach with a fallen tree, clear blue water, and a forested shoreline.

Chatham Seafarer Inn

Chatham

Near the beach

$220

$252 total

includes taxes & fees

Sep 22 - Sep 23

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 restaurant with long communal tables and booths, large windows, and a view of buildings outside.

A garden with a pergola structure, a pathway, and a seating area.

Chatham Wayside Inn

Chatham

Pool loungers
Near the beach

$396

$497 total

includes taxes & fees

Sep 16 - Sep 17

A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.

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.

A dining area with a glass table, chairs, and a vase with flowers.

A circular wooden structure with illuminated edges in a garden setting.

Pleasant Bay Village Resort

Chatham

Outdoor pool
Hot tub

$242

$276 total

includes taxes & fees

Sep 22 - Sep 23

A cozy room with a wicker sofa, two chairs, a small table, and large windows with a view of trees.

A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.

A residential area with a house, a driveway, and a garden with flowering bushes.

The Chatham Motel

Chatham

Near the beach

$281

$321 total

includes taxes & fees

Sep 8 - Sep 9

A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

A pathway leading to a beach with boats in the background and a building with a tower.

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.

A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

Chatham Bars Inn

Chatham

On private beach
Full-service spa

$561

$642 total

includes taxes & fees

Sep 20 - Sep 21

A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.

A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.

A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.

A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

Olde Tavern Motel And Inn

Orleans

Pool loungers
Near the beach

$112

$128 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with lounge chairs and a building in the background.

A blue door labeled "Office" with a small window and a mailbox.

A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

Handkerchief Shoals Inn

South Harwich

Near the beach

$151

$173 total

includes taxes & fees

Sep 14 - Sep 15

A hotel with a pool area, multiple balconies, and a fenced deck with lounge chairs.

A miniature golf course with two holes, a small pond, and a wooden bridge.

A beverage station with a Coca-Cola machine, ice dispensers, and a variety of drink options.

A hotel room with two beds, a desk, a television, and a window with curtains.

Holiday Hill Inn & Suites

Dennis Port

Pool loungers
Near the beach

$119

$136 total

includes taxes & fees

Sep 8 - Sep 9

A clear swimming pool with blue lounge chairs and a blue umbrella.

A golf course with sand bunkers, trees, and a clear blue sky.

An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

Three children playing in shallow water on a beach.

The Villages at Ocean Edge

Brewster

3 outdoor pools
2 indoor pools
3 poolside bars
Children's pool
On private beach
Hot tub

$169

$239 total

includes taxes & fees

Sep 20 - Sep 21

A pool area with lounge chairs, a hot tub, and string lights.

A modern living room with a blue sofa, a coffee table, a large window, and a surfboard decoration.

A room with arcade games, a TV, a large window, and a plant.

A modern living room with a large blue sectional sofa, a woven coffee table, and a large window offering a view of the street.

Dennis Port Surf Club (Boutique Hotel)

Dennis Port

Outdoor pool
Near the beach

$98

$112 total

includes taxes & fees

Sep 9 - Sep 10

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.

A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.

A garden area with a welcome sign, outdoor seating, and a blue umbrella.

A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

Rodeway Inn Orleans - Cape Cod

Orleans

Near the beach

$106

$121 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with a fenced area, lounge chairs, and a building in the background.

A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.

A bathroom with a toilet, sink, and shower.

Skaket Beach Motel

Orleans

Pool
Free breakfast
Free parking
Free WiFi
Air conditioning
Laundry facilities

$140

$160 total

includes taxes & fees

Sep 13 - Sep 14

A nighttime pool area with lounge chairs and a lifebuoy.

A sign for the Escape Inn Hotel with the address 1237.

A two-story building with a white picket fence, a 'No Lifeguard on Duty' sign, and a 'Shallow Water No Diving' warning sign.

A hotel with a white facade, a covered outdoor seating area with white chairs and tables, and a view of the sunset.

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

A backyard with a swimming pool, a stone pathway, and a white fence.

A spacious living area with a round dining table, a sofa, and a ceiling fan.

A modern living room with a sofa, two armchairs, a coffee table, and a side table. There is a large mirror on the wall, a window with curtains, and a door leading outside.

A modern bathroom with a glass-enclosed shower, white vanity, and a large mirror.

Love Farms Lodge

West Dennis

Pool
Free parking
Free WiFi
Connecting rooms available
Air conditioning

$122

$150 total

includes taxes & fees

Sep 28 - Sep 29

A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.

A room with nautical-themed decor, including a map, anchor-patterned rug, and a view of the sea through the window.

A compact room with a kitchenette, a dining table with four chairs, a lamp, and a painting on the wall.

A blue outdoor seating area with picnic tables and umbrellas, surrounded by a wooden fence and trees.

A Beach Breeze Inn

West Harwich

Pool loungers
Near the beach

$144

$165 total

includes taxes & fees

Oct 1 - Oct 2

A building with a blue awning labeled "GRILLROOM" and a covered outdoor seating area with white benches.

A sliding glass door leading to a deck with a white railing and a blue chair.

A row of white, two-story buildings with a white fence in front, likely a motel or small hotel.

Blue Rock Resort

South Yarmouth

Pool loungers
On private beach

$143

$165 total

includes taxes & fees

Sep 8 - Sep 9

A pool area with lounge chairs and umbrellas, surrounded by trees.

A wooden boardwalk leading to a covered area with a view of the sunset over the ocean.

A two-story house with a covered porch, a brick pathway leading to the entrance, and a well-maintained lawn.

A bedroom with a large bed, two wall-mounted picture frames, a window with a view, and a wicker chair.

Charm on Main by Ocean Edge

Sea Pines

Pool loungers
Near private beach
Full-service spa

$173

$198 total

includes taxes & fees

Sep 8 - Sep 9

An aerial view of a residential property with a swimming pool, a gazebo, and a well-maintained lawn.

A kitchen with a white island, a fireplace, and a surfboard decoration.

A building with a red door, black shutters, and hanging flower baskets.

A sandy beach with gentle waves and a clear sky.

Eagle Wing Inn - Cape Cod

Eastham

Outdoor pool
Pool loungers
Near the beach

$164

$188 total

includes taxes & fees

Sep 22 - Sep 23

A swimming pool with blue lounge chairs aligned along the edge.

A reception area with a blue and white color scheme, a map on the wall, and a bookshelf filled with travel brochures.

A hotel room with two beds, a desk, a chair, a lamp, and artwork on the walls.

A wooden picnic table with a white umbrella, surrounded by greenery and a blue wall.

GuestLodge

West Dennis

Outdoor pool
Near the beach

$72

$83 total

includes taxes & fees

Oct 1 - Oct 2

See more properties

Discover your perfect hotel with a pool in Chatham

Breakfast included

Hot tub

4 stars

5 stars

Spa

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.

See properties

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?

See properties

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?

See properties

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?

See properties

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.

See properties

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.

See properties

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?

See properties

Chatham Seaside Links

9.2/10 (20 reviews)

You might want to play some rounds at Chatham Seaside Links, located 0.4 mi (0.7 km) from central Chatham. Why not take a stroll along the beaches and watch the sunset while you're here? If Chatham Seaside Links doesn't quite scratch your golfing itch, Captains Golf Course, and Captain's Cove Golf Course are also nearby.

See properties

Keep exploring

More ways to book

Book Hotels with a Pool in Chatham on Hotels.com