Find Hotels with a Pool in Weatogue, CT

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Check availability on Weatogue Hotels with a Pool

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Weatogue hotels with a pool

Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is NT$3,203
NT$3,578 total
includes taxes & fees
Jan 28 - 2026/1/29
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$7,914
NT$9,892 total
includes taxes & fees
Jan 5 - 2026/1/6
Prospect Berkshires
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is NT$3,454
NT$3,859 total
includes taxes & fees
Jan 6 - 2026/1/7
The Little Lion
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NT$4,679
NT$6,630 total
includes taxes & fees
Jan 26 - 2026/1/27
The Red Lion Inn
Indoor pool
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NT$4,240
NT$4,736 total
includes taxes & fees
Jan 14 - 2026/1/15
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (812)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NT$4,013
NT$5,097 total
includes taxes & fees
Jan 25 - 2026/1/26
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$5,161
NT$5,935 total
includes taxes & fees
Jan 6 - 2026/1/7
Blackberry River Inn
Seasonal outdoor pool
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (273)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is NT$5,624
NT$6,468 total
includes taxes & fees
Jan 1 - 2026/1/2
Interlaken Inn & Resort
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is NT$2,826
NT$3,157 total
includes taxes & fees
Dec 31 - 2026/1/1
Sunset Inn
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat Lodge
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 Weatogue Hotel Reviews

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"Excellent location!!"
Abdul Samad 1-night trip
Posted 4 days ago
Travelodge by Wyndham Great Barrington Berkshires

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. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Provides buffet, an indoor pool, and complimentary wired internet access. Quality Inn Great Barrington: Offers full, an indoor pool, and complimentary wired internet access. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Provides 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, Great Falls, and Mount Frissell.
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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