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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Hampshire County condo rentals

A heated pool

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
Exterior

2. Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
9.0 out of 10, Wonderful, (2 reviews)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Pool

3. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
The price is AED 713
AED 1,374 total
includes taxes & fees
15 Sep - 16 Sep
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Spa

4. 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!
Exterior

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
TV, fireplace, books

6. 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!
Exterior

7. Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View
Lenox
8.0 out of 10, Very Good, (2 reviews)
"Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing."
United States
Maria C.
Peaceful 1BR Condo with Pond View
Property grounds

8. 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, (46 reviews)
"Colin was very helpful and made sure we had everything we needed for a great stay "
United States
Maureen W.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Outdoor dining

9. 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
Property grounds

10. 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, (43 reviews)
"Clean, convenient and the highlight of our winter, as always. "
United States
Leah P.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Dining

11. 1 Mi to MGM Springfield: Cozy Winter Duplex!

1 Mi to MGM Springfield: Cozy Winter Duplex!
Six Corners
10.0 out of 10, Exceptional, (16 reviews)
"Everything was great. We enjoyed our stay!"
United States
Terry B.
1 Mi to MGM Springfield: Cozy Winter Duplex!
Outdoor dining

12. 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.
The price is AED 724
AED 1,391 total
includes taxes & fees
15 Sep - 16 Sep
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior

13. 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

14. 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.
Work, Play & Stay! Apt Near Holyoke Medical Center
Coffee/tea maker, fridge, microwave, stovetop

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

Steps to Holyoke Medical Center! Remote-Work Hub
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Perfect property and location for visiting the several surrounding communities."
United States
Tim L.
The price is AED 628
AED 2,076 total
includes taxes & fees
8 Sep - 9 Sep
Steps to Holyoke Medical Center! Remote-Work Hub
Coffee/tea maker, fridge, microwave, oven

16. 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, (16 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!
Interior

17. 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
4 bedrooms, iron/ironing board, WiFi, bed sheets

18. 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
Exterior

19. 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
Interior

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

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

8/10 Good
"The rooms in the coach in are beginning to feel a little outdated and could use a face lift. But still a great place to stop for a quick overnight."
Caroline 1-night trip
Posted less than an hour ago
Publick House Historic Inn and Country Motor Lodge

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