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

Check availability on Madison Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
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.
A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

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.
$220 nightly
$253 total
Nov 2 - Nov 3
Total with taxes and fees
Water's Edge Resort & Spa
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach bar with wooden chairs and a small table, overlooking the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.

2. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
$199 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Sound View Greenport
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A parking lot with a building in the background.
A motel with a large parking lot and multiple rooms.

3. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
$78 nightly
$90 total
Oct 28 - Oct 29
Total with taxes and fees
Clinton Motel
An indoor swimming pool with tiled walls and a ceiling with skylights.
A hotel entrance with a blue and white facade, a sign reading "BW Best Western," and two large planters with red flowers.
A modern lobby with a reception desk, a seating area, and a glass door entrance.
A modern hotel lobby with a sofa, coffee table, and a chandelier.

4. Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
West Haven
  • Dive into this indoor pool paradise, just steps from New Haven's top attractions.
$110 nightly
$126 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
A marina with boats docked, a fire pit table, and outdoor seating.
An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.
A two-story Victorian-style house with a balcony, a porch, and a small tower.

5. 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.
$309 nightly
$356 total
Nov 3 - Nov 4
Total with taxes and fees
Saybrook Point Resort & Marina
A swimming pool with a wooden deck, lounge chairs, and a fence.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.

6. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
$188 nightly
$215 total
Nov 2 - Nov 3
Total with taxes and fees
The Harbor Front Inn
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

7. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
$136 nightly
$155 total
Nov 6 - Nov 7
Total with taxes and fees
The Bentley Hotel Southampton
A poolside wheelchair by a pool with lounge chairs and a potted plant in the background.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.
A hotel room with a large bed, a wooden nightstand, a TV, and a bathroom visible through an open door.
A modern bathroom with a glass shower enclosure, a toilet, a sink with a mirror, and a towel rack.

8. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
Southington
  • Immerse in the refreshing seasonal outdoor pool, a perfect summertime retreat with convenient morning to evening hours.
$103 nightly
$118 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express Southington by IHG
An indoor swimming pool with clear glass walls, yellow chairs, and a modern ceiling design.
A modern hotel with a flat roof, multiple windows, and a covered entrance area.
A modern reception area with a counter, shelves with snacks, and a view of the outside.
An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

9. 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.
$133 nightly
$153 total
Nov 1 - Nov 2
Total with taxes and fees
Home2 Suites by Hilton East Haven New Haven
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A waterfront property with a large house, multiple boats docked, and lush greenery.

10. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
$219 nightly
$250 total
Nov 1 - Nov 2
Total with taxes and fees
Sag Harbor Inn
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 3 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 1 day 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 2 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 2 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.

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