The Best Hotels with a Pool in Orange, CT from ₩189,485 in 2026 | Expedia

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Check availability on Orange Hotels with a Pool

Tonight

May 26 - May 27

Tomorrow

May 27 - May 28

This weekend

May 29 - May 31

Next weekend

Our top choices for Orange hotels with a pool

Indoor pool

Homewood Suites by Hilton Orange New Haven

Orange

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

₩255,162 total

includes taxes & fees

Jun 21 - Jun 22

Outdoor pool

Courtyard by Marriott New Haven Orange-Milford

Orange

Make a splash with your own seasonal outdoor pool sanctuary at this Yale-adjacent hotel.

₩224,253 total

includes taxes & fees

Jun 7 - Jun 8

Free WiFi

Hampton Inn & Suites By Hilton North Haven

North Haven

₩212,397 total

includes taxes & fees

Jun 2 - Jun 3

Indoor pool

Home2 Suites by Hilton East Haven New Haven

The Centre

Splash into relaxation at this East Haven retreat with a refreshing indoor pool escape.

₩226,652 total

includes taxes & fees

Jun 7 - Jun 8

Indoor pool

Wyndham Southbury

Southbury

Dive into refreshing year-round aquatics at this Southbury hotel, where the indoor pool beckons after a day of exploration.

₩189,485 total

includes taxes & fees

May 28 - May 29

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

The Circle Hotel Fairfield

Grasmere

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

₩243,209 total

includes taxes & fees

Jun 2 - Jun 3

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

Heritage Hotel, Golf & Conference Center

Southbury

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

₩246,244 total

includes taxes & fees

May 27 - May 28

Seasonal outdoor pool, pool umbrellas, sun loungers

Redding Retreat with Pool

Redding

₩1,183,243 total

includes taxes & fees

Jun 1 - Jun 2

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Choose what matters most at hotels with a pool in Orange

Breakfast included

Hot tub

Top Orange Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent

"Our stay was for 3 nights . The room was clean and comfortable and quiet . It is pet friendly which alot of pets where staying there I never heard any barking. Staff everyday came in and tidy up bed and added towels. Breakfast was very good. We stopped in at the bar/restaurant and had a few beverages and staff was very friendly and attentive. We will be coming back again."

Trumbull Marriott Shelton

Trumbull Marriott Shelton

6/10 Okay

"Pros: - close to office I was traveling for - comfortable bed - not-feather pillows (feathers do not support my side-sleeping) - small gym and cardio rooms - space to work in room (desk) - neat reading lights on the bed’s headboard Cons: - old property (looks worn; ceiling tile in closet coming down, carpet bunches in places) - bathtub faucet sprays water out during shower (though I suppose the spray was nice for cleaning feet) - no fan for the bathroom (I don’t like not having a fan on during a shower) - room refrigerator did NOT work - asked if fridge could be repaired, but it never was while I was there - pool did not look clean enough to swim in (water looked yellow) [this is specific to the indoor pool; there is also an outdoor pool that I didn’t look at because it was too cold to swim outside] - hot tub listed as amenity, but covered by wooden boards and obviously not available - treadmills are older and squeak a lot during use - breakfast is not included in room price (continental AYCE, but $20+ per person) The price and distance are what I needed for the reason I was in the area, but I would not go out of my way to stay here again, despite the fact that this hotel was rated a little higher than others at a similar price. Not the worst hotel experience I’ve had, just too many cons to not give the other hotels a chance (and possibly pay a little more)."

The Circle Hotel Fairfield

The Circle Hotel Fairfield

8/10 Good

"The central location in Fairfield is ideal. The only complaint was the internet and tv. Our unit was farthest from the main building and likely the router couldn’t generate a strong signal that far. The tv froze as did my iPad and phone when trying to stream. Get a room close to the main building it may help."

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Everything went very well; the cleaning lady was very friendly and attentive. The only thing I didn't like was that when I went down for breakfast, the guy preparing the food had a sour look on his face and a bad attitude—which I don't think is right, because you're not staying there for free, so you should at least receive good treatment."

Frequently asked questions

What are some accommodations with pools in Orange?

Courtyard by Marriott New Haven Orange-Milford: Features a snack bar/deli, a seasonal outdoor pool, and free self parking. Homewood Suites by Hilton Orange New Haven: Offers free self parking, an indoor pool, and complimentary wireless internet access. New Haven Hotel: Provides full, a pool, and free self parking. Omni New Haven Hotel at Yale: Features daily, a seasonal outdoor pool, and free self parking. Motel 6 Milford, CT: Offers complimentary wired internet access, an indoor pool, and free self parking.

What is there to see and do in Orange?

Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Grassy Hill Country Club during your stay. You'll also discover lots of options for restaurants in Orange.

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

You may want to consider a place to stay that has an outdoor pool if you plan to visit Orange in the warmest months of July, August, or June when the average temperature 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 December when the average temperature is 34°F.

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