TOP Hotels with Swimming Pool in Dennis, MA for 2026

Q: What are some accommodation options with pools in Dennis?

Sesuit Harbor House : Hotel located near Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool and free self parking. Margaritaville Resort Cape Cod : Resort located near Cape Cod Beaches. Offers a children's pool, an outdoor pool and a water park. Bayside Resort Hotel : Hotel, 15-minute walk from Main Street Hyannis. Provides a seasonal outdoor pool, an indoor pool and 2 pool bars. Hyannis Travel Inn : Hotel, 4-minute walk from Main Street Hyannis. Features an indoor pool, an outdoor pool and daily. Chatham Bars Inn : Resort, 4-minute walk from Cape Cod Beaches. Offers a private beach, a seasonal outdoor pool and a full-service spa.

Lovely Cape Cod beach scene with colorful sunlit clouds and sun about to drop below the horizon. Vibrant summer sunset captured at Corporation Beach in Dennis, 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 Dennis Hotels with Swimming Pool

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Dennis hotels with a pool

Sesuit Harbor House

Dennis

Splash into Cape Cod charm at this poolside paradise with family-friendly waters and picnic baskets to go.

₹21,284 total

includes taxes & fees

28 May - 29 May

Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets

Kingfisher Lodging

Dennis

Splash into summer fun with this clean Cape Cod motel's seasonal outdoor pool.

₹17,805 total

includes taxes & fees

27 May - 28 May

Hyannis Travel Inn

Hyannis

Splash into summer at this Cape Cod oasis with refreshing indoor and outdoor pools.

₹10,902 total

includes taxes & fees

4 May - 5 May

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.

₹15,388 total

includes taxes & fees

6 May - 7 May

The Escape Inn

Bass River

Immerse in a refreshing summer retreat at this clean, seasonal pool oasis with beach-themed charm.

₹8,726 total

includes taxes & fees

4 May - 5 May

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.

₹11,249 total

includes taxes & fees

4 May - 5 May

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.

₹23,585 total

includes taxes & fees

17 May - 18 May

Seasonal outdoor pool, pool umbrellas, pool loungers

A Beach Breeze Inn

West Harwich

Tranquil outdoor pool creates a shaded sanctuary amid Cape Cod attractions and ocean breezes.

₹14,014 total

includes taxes & fees

4 May - 5 May

View all properties

Choose what matters most at hotels with a pool in Dennis

Breakfast included

4 stars

Top Dennis Hotel Reviews

Cape Sands Inn

10/10 Excellent

"Nice place, parking was easy. Room was good size. Clean and quiet. Pool area was nice too."

Frequently asked questions

What are some accommodation options with pools in Dennis?

Sesuit Harbor House: Hotel located near Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool and free self parking. Margaritaville Resort Cape Cod: Resort located near Cape Cod Beaches. Offers a children's pool, an outdoor pool and a water park. Bayside Resort Hotel: Hotel, 15-minute walk from Main Street Hyannis. Provides a seasonal outdoor pool, an indoor pool and 2 pool bars. Hyannis Travel Inn: Hotel, 4-minute walk from Main Street Hyannis. Features an indoor pool, an outdoor pool and daily. Chatham Bars Inn: Resort, 4-minute walk from Cape Cod Beaches. Offers a private beach, a seasonal outdoor pool and a full-service spa.

What is there to see and do in Dennis?

Spend some time experiencing the great outdoors at Corporation Beach and Mayflower Beach. During your stay, visit sights such as Cape Cod Museum of Art, Cape Playhouse and Cape Cod Beaches.

When is the best time to book a hotel with a pool in Dennis?

Taking the local weather in Dennis into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Dennis is 1222 mm.

Explore a world of travel with Expedia

Book Hotels with Swimming Pool in Dennis on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Dennis Hotels with Swimming Pool