A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Resorts in Hampshire County

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Check prices for these dates

Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

Our top choices for Hampshire County resorts

Indoor pool

1. Sturbridge Host Hotel & Conference Center

Sturbridge Host Hotel & Conference Center
3.0 star property
Sturbridge
6.4 out of 10, (1,003 reviews)
"Beautiful setting but needs renovation. Lovely staff"
United States
Lauren
The price is AED 393
AED 439 total
includes taxes & fees
15 Sep - 16 Sep
Sturbridge Host Hotel & Conference Center
Exterior

2. COZY CABIN IN BERKSHIRES RESORT.

COZY CABIN IN BERKSHIRES RESORT.
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location on the mountain. Perfect for families. We look forward to staying here again whenever we ski at Jiminy."
United States
Jason C.
COZY CABIN IN BERKSHIRES RESORT.
Dining

3. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"great spot and host!"
United States
Jason G.
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Dining

4. Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Hancock
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Dining

5. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Easy booking, great ski weekend. Very positive experience!"
United States
Faith V.
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Dining

6. Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Hancock
10.0 out of 10, Exceptional, (1 review)
"Walked out of the building, straight into my kids skiing lessons, very convenient."
United States
Edson S.
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Dining

7. Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Hancock
10.0 out of 10, Exceptional, (1 review)
"Great property! Great location. Smooth check-in."
United States
erica l.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Dining

8. Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
hancock
10.0 out of 10, Exceptional, (2 reviews)
"This condo was perfect for our family. We had lots of space and we were right on the base of Jiminy peak. I would definitely stay again."
United States
Leanne W.
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Exterior

9. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA

Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Lee
Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Exterior

10. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA

Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Lee
Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Exterior

11. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA

Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Lee
Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Living area

12. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires

July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires
Lee
July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires
Exterior

13. Canyon Ranch Lenox

Canyon Ranch Lenox
3.0 star property
Lenox
Canyon Ranch 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 Hampshire County Hotel Reviews

Quality Inn West Springfield

Quality Inn West Springfield

8/10 Good
"It is an older property but the rooms have been updated. They are clean, I've stayed twice now. Good option for the price point."
Jennifer 3-night trip
Posted less than an hour ago
Quality Inn West Springfield

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