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

Condo Rentals in Hampshire County

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Hampshire County condo rentals

A hot tub area with a wooden gazebo structure, surrounded by a fence, and a view of a lush green landscape.

1. Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock
8.8 out of 10, Excellent, (10 reviews)
"We love Bentley at Jiminy Peak ww have been coming here for 10 years always a great experience "
United States
Aggie S.
Club Wyndham Bentley Brook Resort - 2 Bedroom
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

2. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (8 reviews)
"We had an amazing experience - from START to FINISH - with our host and overall accomodations! Highly recommend a stay in this spacious condo; we will definitely be returning in the near future."
United States
Leanne T.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A ski resort with a large crowd, a building with a sign, and a clear sky.

3. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Hancock
10.0 out of 10, Exceptional, (48 reviews)
"Our group LOVED this home. The location and cleanliness cannot be beat. All the comforts of home. We highly recommend this condo. We would love to return in the fall.Thank you Colin"
United States
James H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
A snowy outdoor area with people, a building, and a hill in the background.

4. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Hancock
9.8 out of 10, Exceptional, (45 reviews)
"Great location and fabulous host, very helpful and kind."
United States
Richard H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
A large, multi-story residential building with a pond in the foreground.

5. Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
8.8 out of 10, Excellent, (3 reviews)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

6. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is AED 893
AED 1,846 total
includes taxes & fees
12 Nov - 13 Nov
Penthouse overlooking downtown Amherst!
A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

7. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (18 reviews)
"lovely place to stay"
United States
Nancy P.
The price is AED 1,154
AED 2,040 total
includes taxes & fees
12 Nov - 13 Nov
UNIQUE - 1BR Country Condo @ Jiminy Peak
A large, multi-story building with a snow-covered roof and a prominent entrance.

8. Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
United States
Christine O.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
A Country Inn with a covered entrance, stone facade, and a white fence.

9. Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Spacious, comfortable, clean, and perfectly located for activities on the mountain and in the surrounding area. Parking was easy. The pool was nice."
United States
Justin L.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
A cozy living room with a stone fireplace, a large sofa, and a television.

10. Berkshires Getaway < 1 Mi Skiing & Hiking!

Berkshires Getaway < 1 Mi Skiing & Hiking!
Charlemont
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful spot, great location right at the mountain! We had such a great time here!"
United States
Ian M.
Berkshires Getaway < 1 Mi Skiing & Hiking!
A spa room with a hot tub, wooden benches, a window, and wall-mounted lights.

11. Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!

Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
Hancock
9.0 out of 10, Wonderful, (4 reviews)
"Great location, clean and convenient."
United States
Jennifer K.
Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
A large, multi-story residential building with a pond in the foreground.

12. Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View
Lenox
8.6 out of 10, Excellent, (4 reviews)
"Clean and well managed. Needs update of bathroom and stove."
United States
Jackie H.
Peaceful 1BR Condo with Pond View
An outdoor deck with a grill, a table, chairs, and an umbrella.

13. 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"This condo was just as advertised, and a perfect spot about a mile from Jiminy Peak. Marc was a gracious host but we didn't really need him for much. Condo was clean and had all the amenities needed. Great spot."
United States
AWPtvK0AAACqAQICAHhRqf5uyCh4rhrpAEcd0Lr3O2ECPWffSl2fK29sG1pXlAEXDIyjS9Lfhgf6r1JBey7kAAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQEHATAeBglghkgBZQMEAS4wEQQMGHdM80ZH+MkhH73tAgEQgC1FqVTBMbjIddZfQHBgz+GSyzUulTm74hN1W/5sKmcJO7ihg8R8E6963C2HrSDaKM10iydobw2AMCr5VzI9/VL/MFE+THKEeGaPrn5YDAw A.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
A swimming pool with a view of a house and forested hills.

14. Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Hancock
9.2 out of 10, Wonderful, (31 reviews)
"Host was super nice and got back to me so fast. Location is great and would go back again. "
United States
Kelly C.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
A kitchen with dark cabinets, a stainless steel refrigerator, and a countertop. There is a wooden staircase leading to another level.

15. SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot to relax!"
United States
Tisha C.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
A deck with a round table and a covered object, overlooking a green landscape with trees and a clear sky.

16. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior

17. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is AED 209
AED 1,059 total
includes taxes & fees
23 Nov - 24 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A large indoor swimming pool with clear views of mountains through large windows.

18. Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗

Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Hancock
10.0 out of 10, Exceptional, (1 review)
"Absolutely amazing host. There was initial issues with the stay and she stayed up to date and got everything squared away to keep a family vacation on track. 10/10 recommend host!"
United States
Shawn D.
Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

19. Steps to Holyoke Medical Center! Remote-Work Hub

Steps to Holyoke Medical Center! Remote-Work Hub
Holyoke
10.0 out of 10, Exceptional, (6 reviews)
"Perfect property and location for visiting the several surrounding communities."
United States
Tim L.
Steps to Holyoke Medical Center! Remote-Work Hub
A gazebo surrounded by trees, a fire pit, picnic tables, and a wooden walkway.

20. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"Staff and services were outstanding. Great family gathering."
United States
Gerard D.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
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

MGM Springfield

MGM Springfield

10/10 Excellent
"Friendly staff"
Susana 2-night trip
Posted 1 hour ago
MGM Springfield

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