Book the Best Hotels with POOL in Westport in 2026

Q: What are some hotels with pools in Westport?

Delamar Westport : Hotel located near Fairfield University. Features a sauna, an indoor pool, and buffet. Hyatt Regency Greenwich : Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. Trumbull Marriott Shelton : Provides a seasonal outdoor pool, an indoor pool, and 2 restaurants. La Quinta Inn & Suites by Wyndham Stamford / New York City : Offers a snack bar/deli, a seasonal outdoor pool, and free self parking. Ethan Allen Hotel : Hotel located near Fairfield University. Offers daily, a seasonal outdoor pool, and free self parking.

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Our top choices for Westport hotels with a pool

1. Delamar Westport

Westport

CA $512 total

includes taxes & fees

Aug 30 - Aug 31

2. Courtyard by Marriott Norwalk

Cranbury

Immerse in year-round aquatic relaxation at this hotel's warm indoor pool, perfect for families seeking a splash of fun.

CA $233 total

includes taxes & fees

Aug 30 - Aug 31

3. Hilton Garden Inn Norwalk

Cranbury

Float in a year-round indoor oasis with lap lanes and lounge space at this serene hotel.

CA $219 total

includes taxes & fees

Sep 3 - Sep 4

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

4. The Circle Hotel Fairfield

Grasmere

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

CA $240 total

includes taxes & fees

Aug 10 - Aug 11

5. Standard King Bedroom W/Gym & Restaurant on Site!

Historic District

CA $237 total

includes taxes & fees

Aug 23 - Aug 24

6. 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.

CA $205 total

includes taxes & fees

Aug 16 - Aug 17

7. Trumbull Marriott Shelton

Trumbull

Dive into a refreshing aquatic getaway with both indoor and seasonal outdoor pools on site.

CA $260 total

includes taxes & fees

Aug 12 - Aug 13

8. Business or Weekend escape

Stratford

CA $206 total

includes taxes & fees

Aug 6 - Aug 7

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Choose what matters most at hotels with a pool in Westport

Breakfast included

Hot tub

Top Westport Hotel Reviews

Hyatt Place Milford / New Haven

10/10 Excellent

"Incredibly friendly staff, and impressive breakfast"

The Circle Hotel Fairfield

8/10 Good

"I had a nice stay. The rooms were clean and quiet and beds and pillows were comfortable. I wish they had an elevator as carrying my luggage up the stairs was not fun. The breakfast was basic but adequate and they had gluten free Cheerios and hard boiled eggs that I could eat. There were more yummy items if you could eat gluten. Overall a nice stay and walking distance to the beach."

Frequently asked questions

What are some hotels with pools in Westport?

Delamar Westport: Hotel located near Fairfield University. Features a sauna, an indoor pool, and buffet. Hyatt Regency Greenwich: Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. Trumbull Marriott Shelton: Provides a seasonal outdoor pool, an indoor pool, and 2 restaurants. La Quinta Inn & Suites by Wyndham Stamford / New York City: Offers a snack bar/deli, a seasonal outdoor pool, and free self parking. Ethan Allen Hotel: Hotel located near Fairfield University. Offers daily, a seasonal outdoor pool, and free self parking.

What is there to see and do in Westport?

Spend some time experiencing the great outdoors at Compo Beach and Old Mill Beach. During your stay, check out sights such as Levitt Pavilion, Westport Country Playhouse, and Westport Farmers Market.

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

You may want to consider an accommodation that has an outdoor pool if you're planning to visit Westport in the warmest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temp is 35°F.

What's the best way to travel around Westport?

Knowing the transportation options in Westport can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Westport Station or Green's Farms Station. Westport may not have many public transit options so consider a car rental to maximize your time.

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