Hampshire County Holiday Rentals

  • 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

Top Cities in Hampshire County

Fall colors through the trees
Holiday RentalsHoliday Rentals

Southampton

Southampton

Our top choices for Hampshire County holiday rentals

1 bedroom, desk, iron/ironing board, travel cot

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, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is HK$1,411
HK$2,127 total
includes taxes & fees
1 Jun - 2 Jun
The Creation Station is a cozy place so make yourself at home.
Property grounds

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, (13 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 HK$1,497
HK$1,789 total
includes taxes & fees
16 Jun - 17 Jun
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is HK$1,023
HK$1,492 total
includes taxes & fees
2 Jun - 3 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (78 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is HK$952
HK$1,414 total
includes taxes & fees
1 Jun - 2 Jun
comfort, luxury, privacy
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (27 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is HK$1,234
HK$1,677 total
includes taxes & fees
1 Jun - 2 Jun
Newly Built Barn Loft in Pioneer Valley
Fridge, microwave, oven, stovetop

Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (7 reviews)
"The house was very comfortable and we enjoyed our visit very much "
United States
Debbie L.
Historic downtown house. Unscented products and sustainability practices.
Interior

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (4 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 HK$1,856
HK$3,824 total
includes taxes & fees
8 Jun - 9 Jun
Button's Modern Luxury Walkup Downtown Northampton
Outdoor dining

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, (28 reviews)
"the entire place was spotless and exactly like described. the owner brent was awesome. the horses was a great addition to see in the morning 10/10"
United States
Ty
The price is HK$1,034
HK$1,955 total
includes taxes & fees
11 Jun - 12 Jun
Serene 1-bedroom suite on 75 acre horse property
Outdoor dining

Historic downtown apartment. Unscented products and sustainability practices.

Historic downtown apartment. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (11 reviews)
"Quite a find in pricey Northampton. Within easy walking distance to restaurants and shops. Small but very comfortable. We didn't spend much time in the apartment, but it was perfect for what we needed."
United States
Jessica B.
Historic downtown apartment. Unscented products and sustainability practices.
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$762
HK$851 total
includes taxes & fees
2 Jun - 3 Jun
Huttopia Berkshires
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,383 reviews)
"The rooms are very spacious and home like. It is a great place to stay and relay"
United States
Celina
The price is HK$1,078
HK$1,290 total
includes taxes & fees
3 Jun - 4 Jun
Vacation Village in the Berkshires
Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is HK$956
HK$2,326 total
includes taxes & fees
7 Jun - 8 Jun
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Beautifully appointed and comfortable. "
United States
Emily Kate G.
The price is HK$1,011
HK$1,689 total
includes taxes & fees
15 Jun - 16 Jun
Lovely 2nd Floor Apartment
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (29 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,375
HK$2,042 total
includes taxes & fees
2 Jun - 3 Jun
Dove Cabin up in the Trees
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is HK$1,058
HK$1,852 total
includes taxes & fees
7 Jun - 8 Jun
Brookside cottage near the mountains and outdoor recreation
Terrace/patio

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (38 reviews)
"Nice place. "
United States
Liz Y.
The price is HK$1,175
HK$2,745 total
includes taxes & fees
1 Jun - 2 Jun
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
3 bedrooms, desk, iron/ironing board, travel cot

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is HK$1,742
HK$3,666 total
includes taxes & fees
11 Jun - 12 Jun
Townhouse with Pool Table - Renovated w/ King Bed
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is HK$1,175
HK$2,749 total
includes taxes & fees
1 Jun - 2 Jun
Trainmaster's Inn - Caboose
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,567
HK$2,849 total
includes taxes & fees
4 Jun - 5 Jun
Big farmhouse in the foothills of the Berkshires
Property grounds

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, (36 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,425
HK$3,500 total
includes taxes & fees
1 Jun - 2 Jun
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.
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

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

4/10 Poor
"I had 2 rooms they were not dirty just dumpy. Both bath tubs had rust in them. There was no pool as advertised. no hot breakfasts just grab bags to go. Restrooms In Lobby was locked had to ask for key from manager. Walls had scuffed marks. When speaking to manager about conditions made excuses what advertised said had no knowledge what was being said explained 3rd party was the blame. I asked for refund."
Gloria 1-night trip
Posted 2 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport