Find hotels with pools in Wooster Square, New Haven from $105

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Check availability on Wooster Square Hotels with a Pool

Our top choices for Wooster Square hotels with a pool

Indoor pool
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton
2.5 star property
Shelton
8.6 out of 10, Excellent, (1001)
"Nice , comfortable stay :)"
United States
Laura
$103 nightly
The price is $119
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn by Hilton Shelton
Indoor pool
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
3.0 star property
Southington
8.2 out of 10, Very Good, (1002)
"Highly recommend staying here. The rooms are clean and the staff go above and beyond to make sure that guests have a comfortable stay."
United States
Veronica
$91 nightly
The price is $105
Dec 25 - Dec 26
Total with taxes and fees
Holiday Inn Cheshire - Southington by IHG
Indoor pool
Hilton Garden Inn Milford

Hilton Garden Inn Milford

Hilton Garden Inn Milford
3.0 star property
Milford
8.4 out of 10, Very Good, (1003)
"It was a nice stay for the price "
United States
karla
$92 nightly
The price is $106
Dec 19 - Dec 20
Total with taxes and fees
Hilton Garden Inn Milford
Fitness facility
Hyatt House Shelton

Hyatt House Shelton

Hyatt House Shelton
3.0 star property
Shelton
8.4 out of 10, Very Good, (1002)
"Always a pleasure to stay here 1s a year keep coming back!!"
United States
Mark
$118 nightly
The price is $136
Dec 16 - Dec 17
Total with taxes and fees
Hyatt House Shelton
Indoor pool
Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven
3.0 star property
Orange
9.2 out of 10, Wonderful, (1000)
"The room was clean the staff was great "
United States
Nicholas
$111 nightly
The price is $128
Dec 21 - Dec 22
Total with taxes and fees
Homewood Suites by Hilton Orange New Haven
Indoor pool
Wyndham Southbury

Wyndham Southbury

Wyndham Southbury
3.0 star property
Southbury
8.2 out of 10, Very Good, (1064)
"Nice room, friendly staff!"
United States
Scott
$93 nightly
The price is $107
Dec 21 - Dec 22
Total with taxes and fees
Wyndham Southbury
Indoor pool
Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford
3.0 star property
Stratford
8.8 out of 10, Excellent, (1002)
"Very friendly staff, clean hotel and very relaxing atmosphere."
United States
Eugenia
$102 nightly
The price is $117
Jan 10 - Jan 11, 2026
Total with taxes and fees
Homewood Suites by Hilton Stratford
Indoor pool
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
2.5 star property
West Haven
8.0 out of 10, Very Good, (1485)
"Carpet in room needs changing Breakfast very good Staff is great"
United States
carolyn
$96 nightly
The price is $110
Dec 16 - Dec 17
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
Indoor pool
Holiday Inn Express Branford-New Haven by IHG

Holiday Inn Express Branford-New Haven by IHG

Holiday Inn Express Branford-New Haven by IHG
3.0 star property
Branford
8.8 out of 10, Excellent, (1000)
"Nice clean rooms (very big) and varied breakfast selection. Dinner options within walking distance to the hotel. "
United States
Wendy
$97 nightly
The price is $112
Dec 28 - Dec 29
Total with taxes and fees
Holiday Inn Express Branford-New Haven by IHG
Indoor pool
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven
3.0 star property
The Centre
9.6 out of 10, Exceptional, (443)
"Clean, spacious and the staff is great! Second time there in the last 6 months and will continue to stay there every time I go to CT. "
United States
Frances
$111 nightly
The price is $128
Dec 23 - Dec 24
Total with taxes and fees
Home2 Suites by Hilton East Haven New Haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wooster Square Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Little dated but very nice for the price."
Anthony 1-night trip
Posted 2 days ago
Wyndham Southbury

Frequently asked questions

What are some accommodations with pools in Wooster Square?
Motel 6 New Haven - Branford, CT: Features a snack bar/deli, an indoor pool, and complimentary wired internet access. New Haven Hotel: Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Cambria Hotel New Haven University Area: Offers buffet, a pool, and complimentary wired internet access. Wyndham Southbury: Features full, a pool, and free self parking. Omni New Haven Hotel at Yale: Provides a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Wooster Square?
Enjoy a stroll along the shore at Sandy Point Beach and Oak Street Beach. Discover sights such as Wooster Square during your stay.
When is the best time to book a hotel with a pool in Wooster Square?
You may want to consider a place to stay that has an outdoor pool if you'll be visiting in the hottest months of July, August, or June when the average temperature is 70°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 temp is 35°F.

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