Condo Rentals in Hampshire County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Hampshire County condo rentals

Lobby

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,209 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$811
HK$991 total
includes taxes & fees
29 Jan - 30 Jan
Vacation Village in the Berkshires
A heated pool

Condo in Hancock

Club Wyndham Bentley Brook Resort - 2 Bedroom
8.4 out of 10, Very good, (6 reviews)
"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
Exterior

Condo in Hancock

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
10.0 out of 10, Exceptional, (3 reviews)
"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

Condo in Hancock

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
10.0 out of 10, Exceptional, (14 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!
Outdoor dining

Condo in Hancock

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
7.2 out of 10, Good, (11 reviews)
"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 HK$1,123
HK$2,719 total
includes taxes & fees
26 Jan - 27 Jan
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior

Condo in Lenox

Tranquil Lakeside Escape in the Berkshires
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

Condo in Hancock

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
10.0 out of 10, Exceptional, (36 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
Property grounds

Condo in Hancock

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, (41 reviews)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
United States
Dan H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Exterior

Condo in Hancock

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
10.0 out of 10, Exceptional, (1 review)
"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
4 bedrooms, iron/ironing board, WiFi, bed sheets

Condo in Enfield

Spacious 4-bedroom condo with AC and WiFi in charming 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
Interior

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
The price is HK$1,257
HK$3,033 total
includes taxes & fees
8 Feb - 9 Feb
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is HK$1,077
HK$2,353 total
includes taxes & fees
28 Jan - 29 Jan
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

Condo in Hancock

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

Condo in Lenox

Peaceful 1BR Condo with Pond View
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

Condo in Pine Point

Welcome to Honey Spot!
9.8 out of 10, Exceptional, (27 reviews)
"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 HK$1,014
HK$2,309 total
includes taxes & fees
2 Feb - 3 Feb
Welcome to Honey Spot!
Exterior

Condo in Hancock

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.0 out of 10, Wonderful, (27 reviews)
"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
Dining

Condo in Williamstown

Charming 3-bedroom condo with WiFi in Williamstown, MA
Charming 3-bedroom condo with WiFi in Williamstown, MA
Interior

Condo in Northampton

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
10.0 out of 10, Exceptional, (1 review)
"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 traveller
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Exterior

Condo in Hancock

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

Condo in Pittsfield

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
8.0 out of 10, Very good, (1 review)
"Convenient location. Noisy guests in room above ours. "
United States
Anne C.
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hampshire County Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Accommodating staff!"
Kelly 1-night trip
Posted 22 hours ago
The Williams Inn

Find out more about Hampshire County

Hampshire County Condo Rentals information

Number of reviews
2,365
Accommodation
52 Condo Rentals
Lowest Price
HK$991
Highest Price
HK$3,033

Frequently asked questions

Why book your condo in Hampshire County with Expedia?
Holidaying should be hassle-free, so if you're in search of condos at a competitive rate, Expedia delivers. Keep costs down and opt for something small and affordable, or splurge on a 5-star condo and treat your loved ones. Use our search filters to find a stay in Hampshire County that meets your needs.
How can I find cheap condos in Hampshire County?
Expedia can help you narrow down your search for cheap condos in Hampshire County. To reserve a fantastic stay in a couple of clicks, use our handy filter tool to refine your search by star rating, budget and amenities.

Explore a world of travel with Expedia