Condo Rentals in Hampshire County

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Top Cities in Hampshire County

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Northampton

Northampton

Condo Rentals in Hampshire County

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Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2153)
"Great place!"
United States
Nicole
The price is AED 299
AED 375 total
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the Berkshires
Exterior
Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom

Hancock
8.0 out of 10, Very Good, (4)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
United States
Ellamae G.
Club Wyndham Bentley Brook Resort - 2 Bedroom
Living area
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Hancock
10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
United States
Robert
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
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, (14)
"We'll be back!"
United States
Jeanne D.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock
8.0 out of 10, Very Good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
The price is AED 507
AED 1,247 total
includes taxes & fees
15 Dec - 16 Dec
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Property grounds
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (36)
"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
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, (41)
"We loved our stay at this condo! It was immaculate, comfortable, and convenient to all of the local spots we wanted to visit. Our host, Colin, was very responsive. We would definitely stay here again. It would likely be fabulous in the fall too!"
United States
Kathy C.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
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, (1)
"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
Microwave, oven, stovetop, dishwasher
Charming Chateau close to Airport

Charming Chateau close to Airport

Windsor Locks
Charming Chateau close to Airport
Microwave, oven, stovetop
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)
"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.
The price is AED 459
AED 1,545 total
includes taxes & fees
31 Dec - 1 January 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is AED 1,098
AED 2,068 total
includes taxes & fees
1 Dec - 2 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
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, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is AED 503
AED 1,108 total
includes taxes & fees
1 Dec - 2 Dec
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
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)
"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
Property grounds
Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View

Lenox
8.0 out of 10, Very Good, (2)
"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
Welcome to Honey Spot!

Welcome to Honey Spot!

Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is AED 477
AED 1,083 total
includes taxes & fees
31 Dec - 1 January 2026
Welcome to Honey Spot!
Exterior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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

Hancock
9.0 out of 10, Wonderful, (27)
"We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. "
United States
Nicole S.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Outdoor dining
Charming 3-bedroom condo with WiFi in Williamstown, MA

Charming 3-bedroom condo with WiFi in Williamstown, MA

Williamstown
Charming 3-bedroom condo with WiFi in Williamstown, MA
Fridge, microwave, oven, stovetop
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

Northampton
10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
United States
Anonymous traveler
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

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

Hancock
10.0 out of 10, Exceptional, (6)
"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
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 Windsor Locks, CT - Hartford

Motel 6 Windsor Locks, CT - Hartford

10/10 Excellent
"Perfect for waiting on a delayed flight "
kerry 1-night trip
Posted 8 hours ago
Motel 6 Windsor Locks, CT - Hartford

Frequently asked questions

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