Hampshire County Holiday Rentals

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Top Cities in Hampshire County

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Holiday RentalsHoliday Rentals

Southampton

Southampton

Our top choices for Hampshire County holiday rentals

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$1,022
HK$1,483 total
includes taxes & fees
10 Jun - 11 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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$1,410
HK$2,153 total
includes taxes & fees
22 Jun - 23 Jun
The Creation Station is a cozy place so make yourself at home.
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$1,660 total
includes taxes & fees
9 Jun - 10 Jun
Newly Built Barn Loft in Pioneer Valley
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$1,387
HK$1,656 total
includes taxes & fees
16 Jun - 17 Jun
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
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$1,413 total
includes taxes & fees
9 Jun - 10 Jun
comfort, luxury, privacy
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$1,954 total
includes taxes & fees
11 Jun - 12 Jun
Serene 1-bedroom suite on 75 acre horse property
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$3,849 total
includes taxes & fees
9 Jun - 10 Jun
Button's Modern Luxury Walkup Downtown Northampton
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,390 reviews)
"So clean and spacious, had everything you need for a nice getaway"
United States
Melissa
The price is HK$1,010
HK$1,214 total
includes taxes & fees
14 Jun - 15 Jun
Vacation Village in the Berkshires
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$761
HK$851 total
includes taxes & fees
10 Jun - 11 Jun
Huttopia Berkshires
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is HK$910
HK$1,576 total
includes taxes & fees
9 Jun - 10 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, (30 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,375
HK$2,033 total
includes taxes & fees
11 Jun - 12 Jun
Dove Cabin up in the Trees
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, (39 reviews)
"Nice place. "
United States
Liz Y.
The price is HK$1,175
HK$2,791 total
includes taxes & fees
15 Jun - 16 Jun
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"Everything great!"
United States
Andrew P.
The price is HK$3,134
HK$4,717 total
includes taxes & fees
12 Jun - 13 Jun
Bear Creek Cabin
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, (147 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
1 Jul - 2 Jul
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is HK$1,868
HK$2,857 total
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington
Pool

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is HK$1,861
HK$4,039 total
includes taxes & fees
9 Jun - 10 Jun
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Smart TV, fireplace, video games, books

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (40 reviews)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is HK$1,567
HK$2,986 total
includes taxes & fees
4 Jul - 5 Jul
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (32 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is HK$529
HK$1,119 total
includes taxes & fees
9 Jun - 10 Jun
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Sailing, kayaking, fishing

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Stafford Springs
The price is HK$1,481
HK$1,832 total
includes taxes & fees
14 Jun - 15 Jun
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,142
HK$2,912 total
includes taxes & fees
10 Jun - 11 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"As a solo female traveler, I was a bit surprised at the location of my “first” room. I was at the very end of the hall, next to the stair well and across from the trash room. The hallway did smell a bit because the trash room door was propped open but the room itself did not. I was not comfortable with the location so requested a room change - something closer to an elevator - more in the mix and was accommodated without question. The room was very clean, comfortable and I felt better in the new location ."
Lauren 1-night trip
Posted 2 hours ago
Sheraton Hartford Hotel at Bradley Airport