The Best Hotels with a Pool in Lanesborough, MA from ￥11,865 in 2026

Q: What are some accommodations with pools in Lanesborough?

Berkshire Village Carriage House - Super Private!! : Provides daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel : Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires : Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn : Hotel, 15-minute walk from National Shrine of the Divine Mercy. Provides 3 restaurants, an outdoor pool, and spa services.

WW2 Vetrans War Memorial Veterans War Memorial located in Lanesborough, MA The summit of Mt. Greylock

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Our top choices for Lanesborough hotels with a pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

￥25,217 total

includes taxes & fees

Jun 29 - Jun 30

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

￥22,912 total

includes taxes & fees

Jun 21 - Jun 22

The Little Lion

Great Barrington

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

￥15,851 total

includes taxes & fees

Jun 21 - Jun 22

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

￥11,865 total

includes taxes & fees

Jun 21 - Jun 22

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

￥16,052 total

includes taxes & fees

Jun 23 - Jun 24

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

￥16,031 total

includes taxes & fees

Jun 22 - Jun 23

Willows Motel Williamstown

Williamstown

Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.

￥14,887 total

includes taxes & fees

Jun 30 - Jul 1

The Red Lion Inn

Stockbridge

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

￥32,820 total

includes taxes & fees

Jul 1 - Jul 2

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Choose what matters most at hotels with a pool in Lanesborough

Breakfast included

4 stars

Top Lanesborough Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Thank you, everything was perfect."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"From check in to check out, my stay was fantastic. Everyone was helpful and friendly. The pool was excellent. clean and comfortable. The breakfast each morning was delicious. The bar and restaurant were great! The hostess and the bartenders were awesome! The dinners I had were delicious. Everyone was attentive and friendly. My hot water in my room for my showers was very nice!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."

Frequently asked questions

What are some accommodations with pools in Lanesborough?

Berkshire Village Carriage House - Super Private!!: Provides daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Provides 3 restaurants, an outdoor pool, and spa services.

What is there to see and do in Lanesborough?

Spend some time experiencing the great outdoors at Mount Greylock State Reservation Visitor Center and Mount Greylock State Reservation. During your stay, check out sights such as Mountain Coaster, Jiminy Peak Mountain Resort, and Barrington Stage Company.

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

Taking into account the local weather in Lanesborough 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 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Lanesborough are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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