Search and Rent Hampshire County Condos

Compare and save

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Top Cities in Hampshire County

What a great lookout
Condo RentalsCondo Rentals

Hadley

Hadley

Our top choices for Hampshire County condo rentals

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)
"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
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!
Exterior

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, (6 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
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)
"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.
$321 nightly
The price is $359
Mar 16 - Mar 17
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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)
"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
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, (38 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
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)
"we had an amazing time. The room is great and the location is perfect. If you’re skiing love having our own parking section love the proximity to the mountain. Love the size and space of the room. Everything is really well taken care of. Also host with extremely responsive to any requests of things that we still needed and we’re super helpful Everything a great VRBO rental should be. thank you so much for a wonderful stay. "
United States
Paul Y.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
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)
"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

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, (28 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
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

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
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 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Mar 16 - Mar 17
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (2 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
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
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
Interior

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
Interior

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, (14 reviews)
"Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! "
United States
lauren t.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

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)
"Clean, up to date and spacious! Great location for beginner skiiers, also easy to access the rest of the mountain."
United States
Genevieve S.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
Pittsfield
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
TV, DVD player, video library

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at Jiminy Peak this weekend. The Wyndham Bentley Brook is at the best location there, and it is very convenient to get on the slopes. We enjoyed skiing and the pool/hot tub."
United States
David W.
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

8/10 Good
"Stayed here many times. Always a positive experience "
Gretchen 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Bradley Airport by IHG

Find out more about Hampshire County

Hampshire County Condo Rentals information

Number of reviews
190
Accommodation
52 Condo Rentals
Lowest Price
$302
Highest Price
$359

Frequently asked questions

Why book your condo in Hampshire County with Expedia?
Vacationing 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