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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Hampshire County condo rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,409 reviews)
"Property is great and stay was great"
United States
Isha
The price is AED 457
AED 550 total
includes taxes & fees
21 Jul - 22 Jul
Vacation Village in the Berkshires
A heated pool

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock
8.8 out of 10, Excellent, (9 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

Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
10.0 out of 10, Exceptional, (1 review)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Property grounds

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, (39 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
Property grounds

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, (43 reviews)
"We had an excellent time slopeside at Jiminy PeakColin was very responsive; the condo was perfect for us!Look forward to returning again!Margo"
United States
Margo D.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Pool

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, (4 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is AED 721
AED 1,371 total
includes taxes & fees
29 Jun - 30 Jun
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior

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, (3 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
Exterior

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)
"Unit was clean and tidy, fully stocked with bathroom and kitchen items. Main bedroom bed was comfortable and the shower was nice and hot. Overall, we enjoyed our short stay."
United States
S W.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Fridge, microwave, stovetop, dishwasher

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 646
AED 2,061 total
includes taxes & fees
8 Jul - 9 Jul
Steps to Holyoke Medical Center! Remote-Work Hub
TV, fireplace, books

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!
Spa

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

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

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
Outdoor dining

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)
"Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!"
United States
Nancy S.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Exterior

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, (29 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
Outdoor dining

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 698
AED 1,485 total
includes taxes & fees
29 Jun - 30 Jun
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior

Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (1 review)
"This is a lovely apartment in a safe neighborhood. Everything is brand new. The location was perfect for us- a 5 minute walk from family we were visiting. We would be happy to stay here again. A few things to be aware of: Because it is so new, there is only salt and pepper in the kitchen. It would be nice if a few starter keurig cups and sugar were provided for coffee for the first morning. Measuring cups and spoons would also be good additions. Although there was no street noise, we could...
United States
Jody G.
Work, Play & Stay! Apt Near Holyoke Medical Center
Dining

1 Mi to MGM Springfield: Cozy Winter Duplex!

1 Mi to MGM Springfield: Cozy Winter Duplex!
Six Corners
10.0 out of 10, Exceptional, (14 reviews)
"It was very clean. Had everything we needed. "
United States
robert p.
1 Mi to MGM Springfield: Cozy Winter Duplex!
Smart TV, fireplace, table tennis, books

Large Mountainside Condo with Private Trail to Grouse Run

Large Mountainside Condo with Private Trail to Grouse Run
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Everything was wonderful. The host was available for anything we needed. The house was extremely clean, it had everything. A great place to stay! Would highly recommend it. "
United States
Beth B.
Large Mountainside Condo with Private Trail to Grouse Run
Fridge, microwave, oven, stovetop

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!
4 bedrooms, iron/ironing board, WiFi, bed sheets

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
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

Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

10/10 Excellent
"Perfect spot right in Enfield, close enough to the speedway for Formula Drift, and every option of food really close by. Target being right around the corner to do some shopping."
Cody 3-night trip
Posted 2 hours ago
Motel 6 Enfield, CT - Hartford

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