Hotels with Swimming Pool in Sheffield, Massachusetts

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Check availability on Sheffield Hotels with Swimming Pool

Tonight
Jan 6 - Jan 7
Tomorrow
Jan 7 - Jan 8
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Sheffield hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is P8,216
P9,177 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires
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, (716)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is P5,792
P6,470 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is P5,979
P6,678 total
includes taxes & fees
Jan 14 - Jan 15
The Yankee, Trademark Collection by Wyndham
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
"great stall and friendly pet friendly place"
United States
bonnie
The price is P5,833
P7,836 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge
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 P6,502
P7,262 total
includes taxes & fees
Jan 11 - Jan 12
The Little Lion
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 P12,531
P15,977 total
includes taxes & fees
Jan 26 - Jan 27
Prospect 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, (817)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is P6,650
P8,583 total
includes taxes & fees
Feb 2 - Feb 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1005)
"Old time charm and hot tub under the stars"
United States
Lori
The price is P8,866
P12,544 total
includes taxes & fees
Jan 14 - Jan 15
The Red Lion Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is P4,669
P5,216 total
includes taxes & fees
Jan 8 - Jan 9
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Very comfortable beds! "
United States
Gerald
The price is P6,573
P7,342 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn & Suites Berkshires-Lenox
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 Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Absolutely fabulous!"
Lisa 1-night trip
Posted 1 day ago
The Red Lion Inn

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee, Trademark Collection by Wyndham: Features 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Hotel located near Tanglewood Music Center. Features a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Sheffield?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Magnolia Bluffs Casino, Three Mile Pond Wildlife Management Area, and Ashley House during your stay.
When is the best time to book a hotel with a pool in Sheffield?
Taking into account the local weather in Sheffield 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 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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