Vacation Homes in Hampshire County

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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

Top Cities in Hampshire County

Main Street Stroll
Vacation HomesVacation Homes

Northampton

Northampton

Compare Vacation Homes in Hampshire County with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 850 total
includes taxes & fees
9 Feb - 10 Feb
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (204)
"Such a cozy cabin for a perfect weekend stay with friends. Located close to multiple ski spots around the area, coming back to the cabin after to relax with hot cocoa and a fire going on. Right down the street is a shop that sells delicious sandwiches too. Owners of the property were super nice and quick to respond with any questions we had. Hoping to come back soon and check this place out during the summer time to enjoy the lake life!"
Peace and quiet on the lake
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Best night's sleep on king size sleigh bed

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

9.8 out of 10, Exceptional, (96)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is SAR 544
SAR 775 total
includes taxes & fees
11 Feb - 12 Feb
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (24)
"Great charming place to stay. Plenty of room to relax, play games, watch TV, and warm up by the wood-burning stove. Owner is very responsive and friendly and less than 10 minutes from Berkshire East. "
Charlemont Retreat on Chickley River w/ EV Charger
Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshires Lakefront Retreat
Sunsets on the lake

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"It was just as shown in the listing. Overall was very clean and comfortable. Futon took a little figuring out to get set up and securing the shower curtain to prevent spilling water on the bathroom floor took a do-over and some clean-up, but in general was very happy with our stay and the host was very courteous and responsive."
The price is SAR 484
SAR 809 total
includes taxes & fees
9 Feb - 10 Feb
Lovely 2nd Floor Apartment
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Welcome to family fun and dining, directly on the lake!

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (104)
"Came to visit family in CT"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

Comfortable Berkshires retreat on mtn resort, SISO

The price is SAR 1,208
SAR 2,494 total
includes taxes & fees
9 Feb - 10 Feb
Comfortable Berkshires retreat on mtn resort, SISO
Charming 4Bds+1crib house with patio Amherst Center
Pool

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is SAR 893
SAR 1,705 total
includes taxes & fees
3 Mar - 4 Mar
Charming 4Bds+1crib house with patio Amherst Center
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

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

10.0 out of 10, Exceptional, (64)
"We had a wonderful stay, thank you! "
The price is SAR 1,178
SAR 2,251 total
includes taxes & fees
12 Feb - 13 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Home in Great Barrington
Interior

Home in Great Barrington

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful experience and stay. "
The price is SAR 750
SAR 1,186 total
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington
Spacious 5-bedroom house steps from UMass Campus, with large backyard.
Dining room

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Spacious 5-bedroom house steps from UMass Campus, with large backyard.
Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths
Dining

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths
Amherst, Perfect Location, UMass, Smith, MHC!
The Valley is known for our picturesque red tobacco barns and expansive cornfields.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
Country Living just minutes from Everything!
It may be cold outside, but it's warm & cozy inside!

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (88)
"We have been staying here at least once a year to ski at the nearby mountains for the past several years. The home is spotless and the amenities are top notch. The house has everything you need to cook a great meal, a huge TV for a cozy movie night, comfortable king beds and the awesome, squeaky clean hot tub. The home is far enough out of town so you feel like you're getting away, while being minutes away from attractions, restaurants and stores. Thank you for sharing your home! We're already...
Hearts Desire is a furnished whole house in a small, colorful garden center.
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Massachusetts Vacation Rental w/ Deck
Easthampton Vacation Rental | 3BR | 1BA | 988 Sq Ft | 3 Steps

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (19)
"Property was nice, clean, easy access to many places. Huge back yard, we had 5 adults, plenty of room for us. It was winter, so we did not utilize the screen porch or the deck so much, this would be a great place for summer visits. Overall, not a bad choice if you want a place to stay in Easthampton. "
Massachusetts Vacation Rental w/ Deck
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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