Hampshire County Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Top Cities in Hampshire County

Aerial panorama of Northampton, Massachusetts, United States on a beautiful day
Vacation HomesVacation Homes

Northampton

Northampton

Our top choices for Hampshire County vacation homes

Smart TV, fireplace, foosball, books

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Great Barrington
10.0 out of 10, Exceptional, (56 reviews)
"We had a great time at this house. The second living/play room was great for the 8 kids we had with us as it gave them a separate space to play. The large front and back yards also provided ample space to get outdoors. The house was clean and well suited for our large group. "
United States
Nathaniel H.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is CA $225
CA $373 total
includes taxes & fees
Mar 15 - Mar 16
Home in Great Barrington
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is CA $158
CA $275 total
includes taxes & fees
Mar 11 - Mar 12
Lovely 2nd Floor Apartment
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is CA $260
CA $409 total
includes taxes & fees
Mar 11 - Mar 12
Family Ski Getaway in the Berkshires
TV, foosball, table tennis

Elegant home w/ mountain views, trail to riverfront, hot tub, dog-friendly, bbq

Elegant home w/ mountain views, trail to riverfront, hot tub, dog-friendly, bbq
Readsboro
10.0 out of 10, Exceptional, (10 reviews)
"Excellent house for family hangout!"
United States
Amy S.
Elegant home w/ mountain views, trail to riverfront, hot tub, dog-friendly, bbq
Interior

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

Amore Estate - beautiful room with many places to explore and relax in.
Lenox
9.2 out of 10, Wonderful, (34 reviews)
"Great stay"
United States
Benjamin C.
Amore Estate - beautiful room with many places to explore and relax in.
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (20 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is CA $537
CA $1,314 total
includes taxes & fees
Mar 15 - Mar 16
Lake House in Sturbridge w/All the Views!
TV, DVD player, books, video library

Peace and quiet on the lake

Peace and quiet on the lake
Sherwood Forest
9.6 out of 10, Exceptional, (234 reviews)
"Great peaceful weekend in this beautiful home. "
United States
Becky F.
Peace and quiet on the lake
Fridge, microwave, oven, stovetop

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington
10.0 out of 10, Exceptional, (31 reviews)
"The Turning Point stay was excellent in every respect. We had a large group (11) and all had great sleeping locations, some with ensuite bathrooms, all in short distance to them. Kitchen was awesome for large group cooking and service. Nothing lacking! Location great for Great Barrington attractions, Guthrie Center, Breweries, food markets, Appalachian Trail hiking a 5 minute drive. Host Mike is very welcoming and responsive to any questions. We would definitely come to stay again!"
United States
Walter M.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
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, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is CA $244
CA $467 total
includes taxes & fees
Mar 11 - Mar 12
Big farmhouse in the foothills of the Berkshires
1 bedroom, desk, iron/ironing board, travel crib

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)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is CA $244
CA $381 total
includes taxes & fees
Mar 16 - Mar 17
The Creation Station is a cozy place so make yourself at home.
Interior

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, (9 reviews)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
The price is CA $168
CA $206 total
includes taxes & fees
Mar 11 - Mar 12
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Property grounds

Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
Goshen
10.0 out of 10, Exceptional, (6 reviews)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Property grounds

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Pittsfield
9.8 out of 10, Exceptional, (154 reviews)
"Perfect location for hosting large groups "
United States
Erica L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Terrace/patio

Berkshires Lakefront Retreat

Berkshires Lakefront Retreat
Sherwood Forest
10.0 out of 10, Exceptional, (19 reviews)
"Everything was great!"
United States
Michael M.
Berkshires Lakefront Retreat
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is CA $305
CA $750 total
includes taxes & fees
Mar 15 - Mar 16
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Exterior

Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!
Lenox
10.0 out of 10, Exceptional, (80 reviews)
"Excellent, wonderful host."
United States
Robert G.
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Easthampton
10.0 out of 10, Exceptional, (33 reviews)
"Love the place, amazing host!!"
United States
Catalina H.
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
TV, fireplace

Relaxing, Holiday Retreat, Pool, fireplace

Relaxing, Holiday Retreat, Pool, fireplace
Brimfield
10.0 out of 10, Exceptional, (33 reviews)
"The house is absolutely beautiful and so well appointed. The backyard and surrounding area is idyllic. We came for a family reunion and it was the perfect spot to gather and catch up with those we hadn't seen in years."
United States
Stephanie P.
Relaxing, Holiday Retreat, Pool, fireplace
Property grounds

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (89 reviews)
"House and location were perfect for our needs. Our family had a great time and would highly recommend this place to anyone!"
United States
Jim M.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Wonderful hotel staff, clean room, and amazing bar!"
Alexis 3-night trip
Posted 3 hours ago
Wellsworth Hotel

Find out more about Hampshire County

Hampshire County Vacation Homes information

Number of reviews
1,133
Accommodation
489 Vacation Homes
Lowest Price
CA $206
Highest Price
CA $1,314

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