A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Hampshire County Holiday Rentals

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Our top choices for Hampshire County holiday rentals

A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

1. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is AU$304
includes taxes & fees
26 Oct - 27 Oct
Newly Built Barn Loft in Pioneer Valley
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

2. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AU$620
includes taxes & fees
26 Oct - 27 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

3. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (38 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is AU$342
includes taxes & fees
28 Oct - 29 Oct
Serene 1-bedroom suite on 75 acre horse property
A modern kitchen with a central island, bar stools, and a bicycle.

4. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is AU$698
includes taxes & fees
27 Oct - 28 Oct
Button's Modern Luxury Walkup Downtown Northampton
A cozy room with two beds, large windows, and a view of a snowy landscape.

5. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AU$394
includes taxes & fees
3 Nov - 4 Nov
The Creation Station is a cozy place so make yourself at home.
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

6. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is AU$743
includes taxes & fees
26 Oct - 27 Oct
Penthouse overlooking downtown Amherst!
A grassy outdoor area with a hammock, chairs, and a stone wall.

7. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is AU$285
includes taxes & fees
26 Oct - 27 Oct
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

8. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property and host. Left a suit accidentally and they were extremely accommodating in helping us get it back."
United States
Kimberly D.
The price is AU$1,390
includes taxes & fees
5 Nov - 6 Nov
Amherst -NEW - Campus Convenience & Social Privacy
A dining area with a long wooden table set for six, surrounded by chairs. There are hanging pendant lights above the table.

9. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (13 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is AU$2,263
includes taxes & fees
4 Nov - 5 Nov
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,794 reviews)
"We had an amazing stay."
United States
Luke
The price is AU$143
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
Exterior

11. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,229 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is AU$168
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

12. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (71 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is AU$361
includes taxes & fees
26 Oct - 27 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

13. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AU$348
includes taxes & fees
26 Oct - 27 Oct
Modern Studio Ideal for Traveling Professionals
Exterior

14. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is AU$443
includes taxes & fees
26 Oct - 27 Oct
Work, Play & Stay! Apt Near Holyoke Medical Center
A house with a staircase leading to a porch, surrounded by snow and string lights.

15. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (13 reviews)
"Nice place"
United States
Tom
The price is AU$363
includes taxes & fees
26 Oct - 27 Oct
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

16. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AU$339
includes taxes & fees
26 Oct - 27 Oct
Modern Studio Ideal for Traveling Professionals
A blue house with a porch, a wooden bench, and a door.

17. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is AU$300
includes taxes & fees
2 Nov - 3 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A hot tub with a wooden deck and chairs, a white building with windows, and a clear sky.

18. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is AU$649
includes taxes & fees
26 Oct - 27 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A modern two-story house with large windows and a balcony.

19. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AU$917
includes taxes & fees
26 Oct - 27 Oct
Cozy Valley View Post & Beam Villa!
A living room with a fireplace, a sofa, a coffee table, and a TV.

20. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AU$328
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in Chicopee
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Beautiful setting. Spacious room. Even the machine-dispensed coffee was good. Five stars."
Anonymous traveller 1-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Hampshire County

Everything you need to know about Hampshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hampshire County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hampshire County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hampshire County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hampshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hampshire County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Hampshire County holiday rentals we have chosen for you start as low as AU$143 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Hampshire County rentals

At Expedia, we put the best Hampshire County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hampshire County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hampshire County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hampshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.