Find Hotels with a Pool in Lakeville, CT

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Lakeville Hotels with a Pool

Our top choices for Lakeville hotels with a pool

Seasonal outdoor pool
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is ￥34,901
￥40,136 total
includes taxes & fees
Dec 14 - Dec 15
Interlaken Inn & Resort
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, (707)
"Great hospitality "
United States
regina maria
The price is ￥16,780
￥18,743 total
includes taxes & fees
Dec 14 - Dec 15
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, (15)
"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 ￥40,492
￥50,448 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ￥17,131
￥19,136 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Little Lion
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, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is ￥21,025
￥23,485 total
includes taxes & fees
Dec 16 - Dec 17
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,596
￥29,435 total
includes taxes & fees
Dec 17 - Dec 18
Blackberry River Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is ￥32,955
￥37,898 total
includes taxes & fees
Dec 12 - Dec 13
Cornwall Inn and Lodge
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
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ￥47,501
￥57,320 total
includes taxes & fees
Dec 14 - Dec 15
The Old Inn On The Green
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.
View all properties

Top Lakeville Hotel Reviews

Cornwall Inn and Lodge

Cornwall Inn and Lodge

10/10 Excellent
"We have stayed at the Cornwall Inn & Lodge two times. We love its charm and cozy atmosphere. It is clean and well maintained, not the most spacious but we're not in town to stay in the room. The beds are comfy, the room was warm and toasty for our Thanksgiving visit. The staff is always polite and helpful. The breakfast they offer is light on sugar and junk food, a refreshing switch from the typical offerings at other hotels. If you are looking for a simple room with a lot of charm, a healthy breakfast, and a sweet, relaxing space to spend the night in the Kent area, this is a perfect option."
James 3-night trip
Posted 6 days ago
Cornwall Inn and Lodge

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Lakeville?
Interlaken Inn & Resort: Features a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. The Litchfield Inn: Offers a sauna, an outdoor pool, and spa services. Days Inn by Wyndham Torrington: Offers cooked-to-order, a seasonal outdoor pool, and free self parking. Quality Inn: Features full, an indoor pool, and complimentary wired internet access.
What is there to see and do in Lakeville?
Make a point to visit attractions like Lake Taghkanic State Park and Mount Frissell. During your stay, check out sights such as Holley-Williams House Museum, Lime Rock Park, and Yoakum Preserve.
When is the best time to book a hotel with a pool in Lakeville?
Taking into account the local weather in Lakeville can help you maximize your time at the pool during your trip. 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 Lakeville are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.