Vacation Homes in Hampshire County

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Top Cities in Hampshire County

Compare 499 Vacation Homes in Hampshire County with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 859 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Village Carriage House - Super Private!!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat

Author Stephen Oates Once Owned

8.0 out of 10, Very Good, (1)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is SAR 821
SAR 1,508 total
includes taxes & fees
1 Apr - 2 Apr
Author Stephen Oates Once Owned

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,059
SAR 3,882 total
includes taxes & fees
4 Apr - 5 Apr
Hancock Village Inn at Jiminy Peak

PICON COZY

7.8 out of 10, Good, (60)
"Peaceful everything just as listed "
The price is SAR 281
SAR 638 total
includes taxes & fees
1 Apr - 2 Apr
PICON COZY

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

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

9.8 out of 10, Exceptional, (97)
"Great stay in Amherst again"
The price is SAR 544
SAR 775 total
includes taxes & fees
1 Apr - 2 Apr
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

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.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"Property was very nice. Quite area. Host was fantastic. "
Peace and quiet on the lake

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (69)
"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."
Lakeside Retreat Just You, The Lake & The View!

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (8)
"We had such a great time staying here with endless games and activities! We would gladly stay here again and recommend to anyone!"
GAMERS HAVEN, River Wine Inn!

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.8 out of 10, Exceptional, (11)
"Great overnight stay! "
The price is SAR 619
SAR 1,082 total
includes taxes & fees
6 Apr - 7 Apr
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (69)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!

Thomas's Cozy Duplex - Centrally Located

8.6 out of 10, Excellent, (10)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
Thomas's Cozy Duplex - Centrally Located

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.4 out of 10, Exceptional, (3)
"We were really only at the house for the late evenings, nights, and mornings. We found the kitchen well stocked to make breakfast (we bought the groceries). The beds were comfortable. Only a couple minor issues that we just handled. The temperature control was preprogrammed to go to 50 degrees in the evening and overnight. We couldn't seem to reprogram it; however, did get it to kick up warmer about midnight or so. The shower in the main floor bathroom was hard to get turned off so the...
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (3)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.
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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