The Best Hotels with a Pool in Fairfield, CT from ₩170,244 in 2026

Q: What are some accommodations with pools in Fairfield?

Hotel Hi-Ho - Contactless Check-In : Offers daily, a seasonal outdoor pool, and free self parking. The Circle Hotel Fairfield : Features complimentary wired internet access, an indoor pool, and LCD televisions. Best Western Plus Fairfield Hotel : Features 2 restaurants, an indoor pool, and complimentary wireless internet access. DUNE Fairfield Beach : Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. New Haven Hotel : Offers continental, an indoor pool, and complimentary wireless internet access.

Sunset at Ash Creek marina, Fairfield, Connecticut.

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Our top choices for Fairfield hotels with a pool

The Circle Hotel Fairfield

Grasmere

Enjoy serene poolside relaxation at this updated Fairfield retreat with umbrellas and loungers for ultimate comfort.

₩215,273 total

includes taxes & fees

Feb 12 - Feb 13

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Heritage Hotel, Golf, Spa & Conference Center

Southbury

Dive into saltwater serenity at this mountain spa retreat with indoor and seasonal outdoor pools.

₩224,101 total

includes taxes & fees

Feb 15 - Feb 16

Hyatt House Shelton

Shelton

Swim year-round in this hotel's refreshing indoor pool, steps from your comfortable suite in the heart of the business district.

₩193,554 total

includes taxes & fees

Mar 2 - Mar 3

Hilton Garden Inn Milford

Milford

Dive into a refreshing getaway at this hotel's spacious indoor pool sanctuary and fitness center.

₩170,244 total

includes taxes & fees

Feb 22 - Feb 23

Homewood Suites by Hilton Stratford

Stratford

Year-round aquatic retreat awaits at this hotel's indoor pool, perfect for leisure and fitness.

₩195,776 total

includes taxes & fees

Mar 7 - Mar 8

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Danbury

Seasonal splash paradise with a refreshing outdoor pool and fitness center creates an invigorating summer escape in Danbury.

₩213,162 total

includes taxes & fees

Feb 8 - Feb 9

Homewood Suites by Hilton Orange New Haven

Orange

Soak up endless relaxation at this hotel's serene indoor pool, perfect for every season.

₩198,739 total

includes taxes & fees

Feb 22 - Feb 23

Ethan Allen Hotel

Danbury

Serene seasonal pool retreat beckons with refreshing dips and resort-like relaxation in a beautiful, quiet setting.

₩170,244 total

includes taxes & fees

Feb 8 - Feb 9

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Choose what matters most at hotels with a pool in Fairfield

Breakfast included

Hot tub

Top Fairfield Hotel Reviews

Hyatt Place Milford / New Haven

10/10 Excellent

"What a great find and value for the money! Our room was so spacious with a sitting area and small kitchenette included, and the bountiful breakfast sealed the deal. We will definitely be back when we’re in the area."

Motel 6 Milford, CT

10/10 Excellent

"My room was immaculate and the staff were very kind and easy to work with check-in was a breeze. It’s a good location near to stores and restaurants. It was very affordable. The shower pressure was great. Everything was great. The beds were comfortable. Sheets white and fresh. As a student, this is a great choice for me. Affordable, clean safe and conveniently located "

Frequently asked questions

What are some accommodations with pools in Fairfield?

Hotel Hi-Ho - Contactless Check-In: Offers daily, a seasonal outdoor pool, and free self parking. The Circle Hotel Fairfield: Features complimentary wired internet access, an indoor pool, and LCD televisions. Best Western Plus Fairfield Hotel: Features 2 restaurants, an indoor pool, and complimentary wireless internet access. DUNE Fairfield Beach: Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. New Haven Hotel: Offers continental, an indoor pool, and complimentary wireless internet access.

What is there to see and do in Fairfield?

Make a point to visit attractions like Penfield Beach and Connecticut Audubon Birdcraft Museum. Discover sights such as Fairfield Theater Company, Fairfield Beach, and Jennings Beach during your stay. The beaches, restaurants, and shopping are just some of the things to enjoy while you're in the area.

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

You may want to consider a place to stay that has an outdoor pool if you will be visiting Fairfield in the hottest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or March when the average temperature is 36°F.

What's the best way to travel around Fairfield?

Knowing the transportation options in Fairfield can help you enjoy the area beyond your hotel pool. To explore the surrounding area, hop aboard a train at Fairfield Station or Fairfield Metro Station. Fairfield might not have very many public transit choices so consider renting a car to explore more.

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