A beach house with a sandy path leading to it, surrounded by grass and overlooking the ocean.

Dennis Port Hotel Guide - Hotels with Pool in Dennis Port, Massachusetts

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Check availability on Dennis Port Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Dennis Port hotels with a pool

A clear swimming pool with blue chairs and umbrellas, a building with blue shutters, and a clear sky.
A grassy area with a building in the background, a flag, and several parked cars.
A large, multi-story beachfront hotel with a prominent balcony and multiple windows.
A waterfront property with outdoor seating, a long pathway, and a view of the sea.

1. Lighthouse Inn

Lighthouse Inn
West Dennis
  • Dive into paradise at this private beachside retreat with a sun-drenched pool, tennis court, and endless seaside recreation.
€165
includes taxes & fees
14 Oct - 15 Oct
Lighthouse Inn
A large beachfront property with a pool, outdoor seating, and a covered patio.
A wooden deck with a table and two green chairs, overlooking a beach with a fence and a building in the background.
A beachfront property with a pool, outdoor seating, and a wooden deck overlooking the beach.
A room with a view of the ocean, a dining table, a wooden dresser, and a door leading to a balcony.

2. The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort
Dennis Port
  • Sun-dappled splendour awaits with three pools, private beach, and coastal charm for refreshing dips.
€113
includes taxes & fees
14 Oct - 15 Oct
The Corsair & Cross Rip Oceanfront Resort
A hotel with a pool area, multiple balconies, and a fenced deck with lounge chairs.
A hotel room with two beds, a desk, a television, and a window with curtains.
A reception desk with a marble top, a wooden panel base, a desk lamp, a potted plant, and a wicker chair with a cushion.
A miniature golf course with two holes, a small pond, and a wooden bridge.

3. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
Dennis Port
  • Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.
Holiday Hill Inn & Suites
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.
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 series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.

4. 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.
€395
includes taxes & fees
12 Nov - 13 Nov
Chatham Bars Inn
An indoor water park with a boat-shaped play area, a boat house, and a large slide.
A spacious lobby with a large blue mural, comfortable seating areas, and a prominent circular floor design.
A cozy lounge area with wicker furniture, a central round table, and a decorative archway with a sign.
A hotel named 'Margaritaville Resort' with a prominent blue roof, large glass entrance, and outdoor seating area.

5. Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod
Hyannis
  • Poolside paradise at this Cape Cod resort with outdoor pools, waterpark, and a lazy river waiting for you.
€198
includes taxes & fees
25 Oct - 26 Oct
Margaritaville Resort Cape Cod
An indoor swimming pool with a wooden ceiling, potted plants, and lounge chairs.
A beachside table with two chairs, a blue umbrella, and a white tablecloth.
A hotel room with a bed, a chair, a table with two glasses of wine, a lamp, and a window with a view of a lake.
A two-story building with a prominent tower, large windows, and a well-lit entrance.

6. Bayside Resort Hotel

Bayside Resort Hotel
West Yarmouth
  • Float between two pools and bask in poolside bliss at this hotel with poolside bars and sunbathing spots.
€102
includes taxes & fees
1 Nov - 2 Nov
Bayside Resort Hotel
A swimming pool with clear blue water, surrounded by a tiled deck and a building with a green roof in the background.
A reception area with a wooden counter, a blue accent wall, and striped armchairs.
A beach with clear skies and gentle waves.
A grassy area with blue Adirondack chairs arranged around a central fire pit. In the background, there are two buildings with a playground structure.

7. Sunbird Cape Cod Resort

Sunbird Cape Cod Resort
West Yarmouth
  • Splash into Cape Cod bliss with indoor and seasonal outdoor pools at this family-friendly resort.
€94
includes taxes & fees
18 Oct - 19 Oct
Sunbird Cape Cod Resort
A pool area with lounge chairs and umbrellas, a diving board, and a view of the ocean.
A patio area with wicker furniture, a fire pit, and a view of the sea.
A room with a view of a dock and water, a table with a patterned tablecloth, and a hanging pendant light.
An aerial view of a coastal resort with a beach, parking area, and a swimming pool.

8. Red Jacket Beach Resort

Red Jacket Beach Resort
Bass River
  • Dive into a refreshing retreat with indoor and outdoor pools, private beach, and poolside bar service.
€158
includes taxes & fees
19 Oct - 20 Oct
Red Jacket Beach Resort
A swimming pool with a tiled edge, a wooden deck, and a covered seating area with chairs and an umbrella.
A beach with clear blue water, a sandy shore, and rocky outcrops.
A building with a sign reading "Kingfisher Oceanside 15".
A bedroom with a bed, a window with curtains, and a view of the outdoors.

9. Kingfisher Oceanside

Kingfisher Oceanside
Dennis Port
  • Splash into seaside bliss at this beachside retreat with seasonal pool just steps from West Dennis beach.
€186
includes taxes & fees
14 Oct - 15 Oct
Kingfisher Oceanside
A covered swimming pool area with lounge chairs and a hot tub.
A two-story building with a grey exterior and white trim.
Beach chairs arranged in rows facing the ocean.
Three white lounge chairs with blue cushions and backs, arranged on a grassy lawn with a view of the beach and dunes in the background.

10. Edgewater Beach Resort

Edgewater Beach Resort
Dennis Port
  • Swim year-round at this oceanfront haven with indoor and outdoor pools for any season.
Edgewater Beach Resort
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Choose what matters most at hotels with a pool in Dennis Port

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Dennis Port Hotel Reviews

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"Very clean room and bathroom. Arcade was fun. Walking distance to breakfast restaurant."
Michael 1-night trip
Posted 7 hours ago
Holiday Hill Inn & Suites
Pelham House Resort

Pelham House Resort

10/10 Excellent
"The room was beautiful! Highly recommend!"
sandra 1-night trip
Posted 7 hours ago
Pelham House Resort
The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort

10/10 Excellent
"Very kind staff and waited for us to arrive to check in later in the day. Very clean."
Shawn 2-night trip
Posted 12 hours ago
The Corsair & Cross Rip Oceanfront Resort
Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)

10/10 Excellent
"Simple but clean and renovated rooms. Quiet area but close to everything that you could want/need. Owner is onsite and is super helpful. Nice little fire pit area, cold brew available in the lobby and nicely stocked coffee/tea (and some snacks) in the rooms. Will 100% recommend to others!"
Emily 3-night trip
Posted 2 days ago
Dennis Port Surf Club (Boutique Hotel)
Bluegreen Vacations The Soundings, an Ascend Collection Resort

Bluegreen Vacations The Soundings, an Ascend Collection Resort

10/10 Excellent
"Everything at this hotel is what I want in a beachside resort. Easy access to the beach, outdoor pool, inside pool and outside hot tub. Kitchenette and fireplace. This was my 3rd stay and I will be back."
Margaret 11-night trip
Posted 6 days ago
Bluegreen Vacations The Soundings, an Ascend Collection Resort

Frequently asked questions

What's it like visiting Dennis Port?
If lounging by a pool is your idea of the perfect getaway, you may want to explore budget-friendly Dennis Port, which has 5 places to stay with pools. During your visit, you can explore attractions such as Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre, and then relax and unwind poolside at one of the accommodation options in Dennis Port that guests like for their pools.
What are some hotels with pools in Dennis Port?
Holiday Hill Inn & Suites: Features a snack bar/deli, a seasonal outdoor pool and free self parking. Bluebird Dennisport: Hotel, 10-minute walk from Cape Cod Beaches. Offers a seasonal outdoor pool, an indoor pool and complimentary wireless Internet access. 2-bedroom resort charming Dennis MA, Oceanfront/private beach Open 8-2 to 8-5: Resort, 3-minute walk from Cape Cod Beaches. Features an indoor pool, an outdoor pool and laundry facilities.
How many hotels with pools will I be able to find in Dennis Port?
Expedia has 5 hotels in Dennis Port for your poolside break.
What is there to see and do in Dennis Port?
The picturesque setting of Sea Street Beach and Cape Cod Beaches showcase the area's natural beauty. Discover sights such as Cape Cod Theatre Company – Home of the Harwich Jr. Theatre, Haigis Beach and Swan Pond during your stay. Dennis Port appeals to visitors with its beautiful beaches and array of dining options.
When is the best time to book a hotel with a pool in Dennis Port?
Taking the local weather in Dennis Port into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Dennis Port is 1223 mm.

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