Book the Best Hotels with POOL in Weatogue in 2026

Q: What are some accommodations with pools in Weatogue?

The Red Lion Inn : Features 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG : Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Quality Inn Great Barrington : Features buffet, an indoor pool, and complimentary wired internet access. The Little Lion : Features a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts. Monument Mountain Motel : Offers a sauna, an outdoor pool, and spa services.

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Our top choices for Weatogue hotels with a pool

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

CA $228 total

includes taxes & fees

Jun 1 - Jun 2

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

CA $147 total

includes taxes & fees

Jun 11 - Jun 12

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

CA $322 total

includes taxes & fees

Jun 4 - Jun 5

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.

CA $210 total

includes taxes & fees

Jun 9 - Jun 10

Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.

CA $153 total

includes taxes & fees

Jun 8 - Jun 9

Little Cat Lodge

Copake Falls

Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.

CA $235 total

includes taxes & fees

Jun 8 - Jun 9

2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

CA $206 total

includes taxes & fees

Jun 1 - Jun 2

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

Cornwall Bridge

Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.

CA $336 total

includes taxes & fees

May 28 - May 29

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Choose what matters most at hotels with a pool in Weatogue

Breakfast included

4 stars

Top Weatogue Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Terrific generous breakfadt menu, cozy eating lounge. The room was in tip top shape and the hotel is superbly located right on Main Street and in walking proximity of shops, stores restaurants and cafes. Ideal place to stay abd reasonably priced room rates."

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"The suite is a great option for a family of five. We have disabled children and found it really easy to get to the pool. The rooms and pool are located in the same building. So we didn’t have to walk through a cold parking lot after swimming. It’s a much better location and quality than a lot of the other similar hotels. it’s already across from a grocery store and local restaurants even a McDonald’s. A great all-around family choice."

Frequently asked questions

What are some accommodations with pools in Weatogue?

The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Quality Inn Great Barrington: Features buffet, an indoor pool, and complimentary wired internet access. The Little Lion: Features a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts. Monument Mountain Motel: Offers a sauna, an outdoor pool, and spa services.

What is there to see and do in Weatogue?

Surround yourself with nature at Housatonic River. During your stay, check out sights such as Mount Riga State Park, Mount Frissell, and Campbell Falls State Park.

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

Taking into account the local weather in Weatogue is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Weatogue are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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