Condo Rentals in Hampshire County

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Top Cities in Hampshire County

Main Street Stroll
Condo RentalsCondo Rentals

Northampton

Northampton

Condo Rentals in Hampshire County

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2030)
"Really nice place at a reasonable price"
The price is AED 337
AED 417 total
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"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."
The price is AED 400
AED 1,448 total
includes taxes & fees
6 Oct - 7 Oct
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very Good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is AED 522
AED 1,231 total
includes taxes & fees
27 Oct - 28 Oct
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

8.0 out of 10, Very Good, (1)
"very nice and roomy! really enjoyed."
The price is AED 500
AED 1,104 total
includes taxes & fees
6 Oct - 7 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Clean and quiet, nicely decorated! "
The price is AED 474
AED 1,280 total
includes taxes & fees
6 Oct - 7 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

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

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. "
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Charming Chateau close to Airport
Microwave, oven, stovetop, dishwasher

Charming Chateau close to Airport

Charming Chateau close to Airport
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Property grounds

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

10.0 out of 10, Exceptional, (41)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

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

10.0 out of 10, Exceptional, (13)
"Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! "
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
Interior

Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

7.0 out of 10, Good, (9)
"Mostly a great stay. The AC which was advertised as an amenity did NOT work. The host did not come to fix it when I complained. Also, no extra blankets or sheets, no hand soap in bathroom or kitchen. We bought and left soap for the next guests. Great kitchen equipment!"
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
Tranquil Lakeside Escape in the Berkshires
Property grounds

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

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."
Peaceful 1BR Condo with Pond View
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Living area

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

10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Welcome to Honey Spot!
Property grounds

Welcome to Honey Spot!

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"
Welcome to Honey Spot!
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

10.0 out of 10, Exceptional, (35)
"Hot tub was nice. We took a chair lift to the top of the mountain. The view was spectacular. The condo was very comfortable and clean. The only thing that can use some improvement is the water pressure in the shower and definitely a new shower head. The one in the bunk room bathroom really needs an upgrade. Otherwise we had a delightful stay."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Exterior

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

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!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

10.0 out of 10, Exceptional, (13)
"We'll be back!"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Exterior

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

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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"All that was needed is a Hot tub for these elderly bones and raise the temperature in the pool "
Frederick 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

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.