A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Find Hotels with a Pool in Madison, CT

  • 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 Madison Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Madison hotels with a pool

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
A balcony with a view of the ocean, a white railing, and two white chairs with blue cushions.
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

1. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
  • Pristine waters await at this coastal retreat with private beach access and year-round pools.
CA $254
CA $316 total
includes taxes & fees
Nov 1 - Nov 2
Water's Edge Resort & Spa
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A motel with a large parking lot and multiple rooms.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

2. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
CA $111
CA $128 total
includes taxes & fees
Nov 1 - Nov 2
Clinton Motel
Pool
A modern hotel room with a large window, a dining area, and a colorful abstract painting on the wall.
A hotel room with two beds, a wooden headboard, a framed picture on the wall, and a door in the background.
A Holiday Inn Express building with a modern design, featuring a covered entrance and a landscaped front yard.

3. Holiday Inn Express Branford-New Haven by IHG

Holiday Inn Express Branford-New Haven by IHG
Branford
  • Splash into aquatic bliss at this modern hotel with an indoor pool and fitness centre.
CA $186
CA $214 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Branford-New Haven by IHG
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.

4. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
CA $138
CA $158 total
includes taxes & fees
Nov 9 - Nov 10
Quality Inn Old Saybrook - Westbrook
An indoor swimming pool with clear glass walls, yellow chairs, and a modern ceiling design.
An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.
A hotel room with two beds, each with a headboard and bedside lamps. There is a small table and a chair in the room.
A modern hotel with a flat roof, multiple windows, and a covered entrance area.

5. Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven
The Centre
  • Splash into relaxation at this East Haven retreat with a refreshing indoor pool escape.
CA $189
CA $217 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton East Haven New Haven
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.
A marina with boats docked, a fire pit table, and outdoor seating.
A marina at sunset with boats docked, a fire feature on the deck, and a chair.

6. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
  • Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
CA $397
CA $506 total
includes taxes & fees
Nov 3 - Nov 4
Saybrook Point Resort & Marina
An indoor swimming pool with clear blue water, surrounded by white lounge chairs and tables.
A hotel room with two beds, a desk, and a chair.
A hotel room with a sofa, two armchairs, a small table with a remote control, a lamp, a bathtub, and a walk-in closet.
An outdoor patio area with tables and umbrellas, a covered seating area, and a view of the building's interior.

7. Baymont by Wyndham Branford/New Haven

Baymont by Wyndham Branford/New Haven
Branford
  • Splash into serene seclusion at this Connecticut hotel with a private pool and sauna.
CA $127
CA $146 total
includes taxes & fees
Nov 1 - Nov 2
Baymont by Wyndham Branford/New Haven
A hotel room with a bed, bedside tables, a desk, a chair, a lamp, and a window.

8. Hampton Inn & Suites By Hilton North Haven

Hampton Inn & Suites By Hilton North Haven
North Haven
CA $168
CA $193 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites By Hilton North Haven
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.
A modern hotel dining area with multiple tables and chairs, a bar area, and a large seating area with a view of the outdoors.
A conference room with a large table, multiple chairs, a flat-screen TV on the wall, and a carpeted floor.
A hotel room with a bed, desk, TV, chair, lamp, and air conditioning unit.

9. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
Wallingford
  • Dive into year-round aquatic bliss at this hotel's pristine indoor pool sanctuary.
CA $191
CA $220 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Wallingford/Meriden
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A beach bar with wooden chairs and a small table, overlooking the sea.
A spacious room with wicker furniture, large windows, and a view of the sea.

10. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
CA $254
CA $330 total
includes taxes & fees
Nov 1 - Nov 2
Sound View Greenport
View all properties

Choose what matters most at hotels with a pool in Madison

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Madison Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Nice place"
Laurie 2-night trip
Posted 17 hours ago
Water's Edge Resort & Spa
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 2 days ago
Sound View Greenport
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"A fairly clean hotel with very nice staff! The only thing that bothered us was the constant smell of weed/marijuana every day we were there."
Denise 3-night trip
Posted 3 days ago
Holiday Inn Express Southington by IHG
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

8/10 Good
"The same breakfast for three days and the last day they have only bagels. The coffee machine out of order."
jose 3-night trip
Posted 3 days ago
Clarion Inn North Haven - New Haven North

Frequently asked questions

What are some accommodations with pools in Madison?
Madison Beach Hotel: Offers a snack bar/deli, a seasonal outdoor pool, and buffet. New Madison beach house - Ocean front- Great views- booking Summer 2026: Provides full, a pool, and free self parking. New Haven Hotel: Offers a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool, and a private beach.
What is there to see and do in Madison?
Make a point to visit attractions like Hammonasset Beach and RJ Julia Booksellers. During your stay, check out sights such as Hammonasset Beach State Park, Allis-Bushnell House and Museum, and Meigs Point Nature Center. Take in the natural beauty of Madison with the beaches.
When is the best time to book a hotel with a pool in Madison?
You may want to consider a place to stay with an outdoor swimming pool if you will be visiting Madison in the hottest months of July, August, or June when the average temp is 70°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temperature is 35°F.
What's the best way to travel around Madison?
Knowing the transportation options in and around Madison can help you enjoy the area beyond your hotel pool. If you want to explore the larger area, hop aboard a train at Madison Station. Madison might not have very many public transportation choices so consider a car rental to maximize your time.

Explore a world of travel with Expedia