A lighthouse with a house nearby, under a starry night sky with visible Milky Way.

Find Hotels with a Pool in North Chatham, MA

  • 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 North Chatham Hotels with a Pool

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for North Chatham hotels with a pool

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 bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.
A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.

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.
₩230,932
₩314,294 total
includes taxes & fees
Oct 18 - Oct 19
Greyfinch Chatham Inn
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 modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.
A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.

2. 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.
₩135,160
₩154,683 total
includes taxes & fees
Oct 5 - Oct 6
Olde Tavern Motel And Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
A beach with a fallen tree, clear blue water, and a forested shoreline.
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.

3. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
₩263,010
₩301,013 total
includes taxes & fees
Oct 7 - Oct 8
Chatham Seafarer Inn
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
A bathroom with a toilet, sink, and shower.
A covered patio with a round table and four chairs.

4. 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.
₩176,189
₩201,648 total
includes taxes & fees
Oct 12 - Oct 13
Skaket Beach Motel
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 covered porch with a lattice design, a stone pathway, and a view of a garden.

5. 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.
₩327,305
₩374,601 total
includes taxes & fees
Oct 6 - Oct 7
Pleasant Bay Village Resort
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.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.

6. 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.
₩367,389
₩479,859 total
includes taxes & fees
Oct 25 - Oct 26
Chatham Wayside Inn
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
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.
A pathway leading to a beach with boats in the background and a building with a tower.

7. 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.
₩568,627
₩650,794 total
includes taxes & fees
Oct 25 - Oct 26
Chatham Bars Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
Three children playing in shallow water on a beach.
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.

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 vacation mood.
₩160,636
₩246,348 total
includes taxes & fees
Oct 25 - Oct 26
The Villages at Ocean Edge
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A garden area with a welcome sign, outdoor seating, and a blue umbrella.

9. 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.
₩143,648
₩164,398 total
includes taxes & fees
Oct 1 - Oct 2
Rodeway Inn Orleans - Cape Cod
A residential area with a house, a driveway, and a garden with flowering bushes.
A building with a blue roof, a white steeple, and a flagpole with an American flag.
A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.

10. 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.
₩252,167
₩288,611 total
includes taxes & fees
Oct 18 - Oct 19
The Chatham Motel
View all properties

Choose what matters most at hotels with a pool in North Chatham

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top North Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Very nice place and reasonable"
Donald 3-night trip
Posted 7 hours ago
Cape Sands Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Un muy buen lugar, perfecto en todas las estaciones del año, aquí hay mucha diversión"
Andres Felipe 1-night trip
Posted 8 hours ago
Margaritaville Resort Cape Cod
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Very welcoming staff, the manager at the front office greet us in the parking lot and also give me a box of chocolates for my birthday"
Merlin 2-night trip
Posted 9 hours ago
Riviera Beach Resort
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Location was ideal. Wished there had been more TV channel options."
David 6-night trip
Posted 16 hours ago
Holiday Hill Inn & Suites
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Friendly staff and a great location. Walkable to downtown, Transportation Center, and ferries. Decent continental breakfast."
Lynne 4-night trip
Posted 21 hours ago
Hyannis Travel Inn
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

10/10 Excellent
"At the end of day to watch tv thru satellite dish is no good the reception and colors streak across screen so often you have to just shut off."
Russell 3-night trip
Posted 1 day ago
All Seasons Resort, Trademark Collection by Wyndham
The Villages at Ocean Edge

The Villages at Ocean Edge

10/10 Excellent
"The unit could use more kitchen amenities. Other than that, no complaints."
Joseph 2-night trip
Posted 2 days ago
The Villages at Ocean Edge
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"Room was clean and cozy. Unique property with onsite food truck. Fire pits lit at night with seating."
Kristine 1-night trip
Posted 3 days ago
Freebird Motor Lodge by Reverie Boutique Collection

Frequently asked questions

What are some accommodations with pools in North Chatham?
Margaritaville Resort Cape Cod: Resort located near Hyannis Harbor. Features a children's pool, an indoor pool, and a water park. Bayside Resort Hotel: Hotel located near Hyannis Harbor. Offers a seasonal outdoor pool, an indoor pool, and 2 pool bars. Uncommoner Hotel by Reverie Boutique Collection: Hotel located near Hyannis Harbor. Provides a seasonal outdoor pool, an indoor pool, and 2 bars. Holiday Inn Express Hyannis Cape Cod by IHG: Hotel located near Hyannis Harbor. Features a children's pool, an indoor pool, and a sauna. Lighthouse Inn: Hotel, 4-minute walk from Cape Cod Beaches. Offers a private beach, a seasonal outdoor pool, and a snack bar/deli.
What is there to see and do in North Chatham?
Make a point to visit attractions like Cape Cod Beaches and Chatham Marconi Maritime Center. Discover sights such as Chatham Shark Center during your stay.
When is the best time to book a hotel with a pool in North Chatham?
Taking into account the local weather in North Chatham can help you maximize your time at the pool during your trip. 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 North Chatham is 54 inches.

Explore a world of travel with Expedia