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

Vacation Rentals in Hampshire County

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Our top choices for Hampshire County vacation 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, (38 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 ￥24,901
￥33,506 total
includes taxes & fees
Oct 18 - Oct 19
Newly Built Barn Loft in Pioneer Valley
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

2. 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 ￥20,347
￥38,385 total
includes taxes & fees
Oct 28 - Oct 29
Serene 1-bedroom suite on 75 acre horse property
A modern kitchen with a central island, bar stools, and a bicycle.

3. 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 ￥38,570
￥79,089 total
includes taxes & fees
Oct 20 - Oct 21
Button's Modern Luxury Walkup Downtown Northampton
A cozy room with two beds, large windows, and a view of a snowy landscape.

4. 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 ￥28,444
￥43,775 total
includes taxes & fees
Nov 16 - Nov 17
The Creation Station is a cozy place so make yourself at home.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

5. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 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 ￥42,665
￥69,650 total
includes taxes & fees
Oct 18 - Oct 19
Charming, updated 3 bedroom farmhouse farm stay.
A grassy outdoor area with a hammock, chairs, and a stone wall.

6. 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)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is ￥29,234
￥34,910 total
includes taxes & fees
Nov 3 - Nov 4
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

7. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our stay!"
United States
Susan N.
The price is ￥94,702
￥119,380 total
includes taxes & fees
Nov 5 - Nov 6
Amherst -NEW - Campus Convenience & Social Privacy
A living room with a flat-screen TV, a striped armchair, a leather sofa, a globe on a stand, and a dining area with a table and chairs.

8. 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 ￥59,258
￥110,319 total
includes taxes & fees
Oct 28 - Oct 29
Penthouse overlooking downtown Amherst!
A bedroom with a four-poster bed, a dresser, a chair, and a large window.

9. Steps from Amherst town common, 3 BR charmer

Steps from Amherst town common, 3 BR charmer
East Village Historic District
The price is ￥39,051
￥49,977 total
includes taxes & fees
Nov 4 - Nov 5
Steps from Amherst town common, 3 BR charmer
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, (2,750 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is ￥12,696
￥15,914 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

11. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is ￥13,680
￥18,812 total
includes taxes & fees
Nov 15 - Nov 16
Berkshire Mountain Lodge
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

12. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 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 ￥19,778
￥33,748 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥10,435
￥39,029 total
includes taxes & fees
Oct 26 - Oct 27
Modern Studio Ideal for Traveling Professionals
A house with a staircase leading to a porch, surrounded by snow and string lights.

14. 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 ￥32,015
￥40,352 total
includes taxes & fees
Oct 26 - Oct 27
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A blue house with a porch, a wooden bench, and a door.

15. 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 ￥11,383
￥34,258 total
includes taxes & fees
Nov 4 - Nov 5
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 ￥15,012
￥38,361 total
includes taxes & fees
Oct 26 - Oct 27
Modern Studio Ideal for Traveling Professionals
Exterior

17. 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 ￥13,906
￥55,424 total
includes taxes & fees
Oct 18 - Oct 19
Work, Play & Stay! Apt Near Holyoke Medical Center
A living room with a fireplace, a sofa, a coffee table, and a TV.

18. 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 ￥24,967
￥36,395 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 2-bedroom apartment in Chicopee
A bedroom with a bed, curtains, a bedside table, and a lamp.

19. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is ￥33,580
￥71,281 total
includes taxes & fees
Oct 28 - Oct 29
Townhouse with Pool Table - Renovated w/ King Bed
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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 ￥35,414
￥78,585 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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

River Valley Inn

River Valley Inn

10/10 Excellent
"This is a remodeled and updated classic motel. Knowing that there was no breakfast provided we made use of the microwave and fridge by bring items for our own breakfast. We had the deluxe room and it was super clean and comfy and the owners were very helpful at the check-in with suggestions and the offer of morning coffee in the office. For the area this is a great bargain and we would stay again if we are back in the vicinity."
Lynn 1-night trip
Posted 3 hours ago
River Valley Inn

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Vacation Apartments in Hampshire County

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