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

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In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Hampshire County

Tulips in a greenhouse with a white wall in the background.
Condo RentalsCondo Rentals

South Hadley

South Hadley

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 ski resort with a large crowd, a building with a sign, and a clear sky.

2. 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)
"Very basic and fairly well kept ski condo. Clean, large bathrooms, bedrooms that can accommodate 9 people, and then a sleeper sofa as well. Convenient in the summer to Williamstown and Mt. Greylock and other attractions. Fun attractions on site as well."
United States
Jeffrey G.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
A large, multi-story residential building with a pond in the foreground.

3. Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
8.8 out of 10, Excellent, (3 reviews)
Tranquil Lakeside Escape in the Berkshires
A large, multi-story residential building with a pond in the foreground.

4. 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
A snow-covered Christmas tree in a courtyard with residential buildings in the background.

5. 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 large, multi-story building with a snow-covered roof and a prominent entrance.

6. 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
Exterior

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

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
$314 nightly
The price is $351
Oct 14 - Oct 15
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
A kitchen with dark cabinets, a stainless steel refrigerator, and a countertop. There is a wooden staircase leading to another level.

8. 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 cozy living room with a stone fireplace, a large sofa, and a television.

9. 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.

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

Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
Hancock
8.8 out of 10, Excellent, (3 reviews)
"Great location, clean and convenient."
United States
Jennifer K.
Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
A snowy outdoor area with people, a building, and a hill in the background.

11. 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, (44 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 swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Four people seated at a table with food and drinks, wearing winter sports helmets.

13. 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
An outdoor deck with a grill, a table, chairs, and an umbrella.

14. 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
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3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

15. 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
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

16. Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Enfield
10.0 out of 10, Exceptional, (2 reviews)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

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

Steps to Holyoke Medical Center! Remote-Work Hub
Holyoke
10.0 out of 10, Exceptional, (5 reviews)
"Perfect property and location for visiting the several surrounding communities."
United States
Tim L.
Steps to Holyoke Medical Center! Remote-Work Hub
A Country Inn with a covered entrance, stone facade, and a white fence.

18. 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)
"The clean room was very comfortable and we enjoyed the mountain view"
United States
Susan C.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
A dining area with a marble table, grey upholstered chairs, and a grey sofa in the background.

19. 1 Mi to MGM Springfield: Cozy Winter Duplex!

1 Mi to MGM Springfield: Cozy Winter Duplex!
Six Corners
10.0 out of 10, Exceptional, (17 reviews)
"Everything was great. We enjoyed our stay!"
United States
Terry B.
1 Mi to MGM Springfield: Cozy Winter Duplex!
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

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

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
8.8 out of 10, Excellent, (5 reviews)
"Staying at the Wyndham made is so easy for us while we were there skiing. The property is right on the slopes and offers a lot of amenities."
United States
Andrew B.
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"It was a great place close to the airport."
Rebecca 1-night trip
Posted 1 hour ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Hampshire County

Hampshire County Condo Rentals information

Number of reviews
221
Accommodation
33 Condo Rentals
Lowest Price
$351
Highest Price
$351

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