Cottages in Hampshire County

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Top Cities in Hampshire County

Aerial panorama of Northampton, Massachusetts, United States on a beautiful day
CottagesCottages

Northampton

Northampton
Great Sacandaga Lake From Hadley Mountain
CottagesCottages

Hadley

Hadley

Our top choices for Hampshire County cottages

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 AED 551
AED 1,287 total
includes taxes & fees
1 Jun - 2 Jun
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances

Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances
Chester
Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances
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 AED 496
AED 868 total
includes taxes & fees
7 Jun - 8 Jun
Brookside cottage near the mountains and outdoor recreation
Exterior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
New Marlborough
9.6 out of 10, Exceptional, (23 reviews)
"Great location close to Butternut. The house had everything we needed for a three night stay, and I received a quick response from the owner when I had a question. We would rent again!"
United States
Lisa S.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

Brimfield Waterfront cottage

Brimfield Waterfront cottage
Brimfield
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful place. Would stay, again!"
United States
Kristi B.
Brimfield Waterfront cottage
Exterior

Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!
Pittsfield
10.0 out of 10, Exceptional, (4 reviews)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
United States
Cade Z.
Lake Views & Dock Access - Pittsfield Cottage!
Exterior

2-bedroom cottage close to hiking and swimming with AC

2-bedroom cottage close to hiking and swimming with AC
New Marlborough
10.0 out of 10, Exceptional, (4 reviews)
"Super cozy house in good location and seamless booking experience. Would definitely stay again."
United States
Adela C.
2-bedroom cottage close to hiking and swimming with AC
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!
3.0 star property
Becket
A-frame Cabin w/ Furnished Deck in Becket!
Terrace/patio

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
United States
Tracey A.
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Outdoor dining

Massachusetts Vacation Rental w/ Deck

Massachusetts Vacation Rental w/ Deck
3.0 star property
Easthampton
Massachusetts Vacation Rental w/ Deck
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass
Otis
8.6 out of 10, Excellent, (9 reviews)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
Exterior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough
9.2 out of 10, Wonderful, (44 reviews)
"Could not have been more relaxing or enjoyable."
United States
Raymond B.
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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 AED 551
AED 1,272 total
includes taxes & fees
31 May - 1 Jun
Trainmaster's Inn - Caboose
Exterior

Relax by the Lake - Cozy Lakefront Retreat with Scenic Views

Relax by the Lake - Cozy Lakefront Retreat with Scenic Views
Charlton
9.6 out of 10, Exceptional, (10 reviews)
"This property was the cleanest vrbo I’ve ever stayed at, the host was very caring and accommodating. I highly recommend this place, they even had snacks for us to enjoy. Great view of the lake and exactly as described. Great value and place to stay!"
United States
Andrew N.
Relax by the Lake - Cozy Lakefront Retreat with Scenic Views
Exterior

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature
Cummington
10.0 out of 10, Exceptional, (214 reviews)
"Beautiful property and accommodations. "
United States
Matt D.
The Clearing - Quiet - Close To Nature
Outdoor dining

Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access!
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Clean cabin close to Sherwood shoppe for food and supplies. "
United States
Lynn F.
Cozy Becket Cottage Escape w/ Lake Access!
Outdoor dining

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Becket
10.0 out of 10, Exceptional, (1 review)
"We spent a lovely, relaxing weekend in this well kept and well situated property. Hoping to come back again."
United States
Jeffrey N.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Exterior

Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock
Lanesboro
10.0 out of 10, Exceptional, (118 reviews)
"We really enjoyed our stay here. The location was perfect & the cottage was absolutely charming!We hope to return soon. "
United States
Cheryl B.
Charming historic cottage on scenic road to Mt. Greylock
Exterior

East Otis Vacation Rental w/ Private Deck & BBQ!

East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis
9.8 out of 10, Exceptional, (11 reviews)
"Lovely location. Quiet getaway. "
United States
Sam F.
East Otis Vacation Rental w/ Private Deck & BBQ!
Terrace/patio

Waterfront Cottage 10 Min From Great Barrington

Waterfront Cottage 10 Min From Great Barrington
New Marlborough
10.0 out of 10, Exceptional, (101 reviews)
"very comfortable, great location on the lake, and near good hiking and nice towns"
United States
John M.
Waterfront Cottage 10 Min From Great Barrington
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"Nice room and restaurant options. Good value for the money. Would stay there again if the opportunity arises."
Tom 1-night trip
Posted less than an hour ago
Publick House Historic Inn and Country Motor Lodge

Frequently asked questions

Why book your cottage in Hampshire County with Expedia?
Expedia has some great cottages in Hampshire County, so get ready for an unforgettable stay on nature's doorstep. If you're sticking to a budget, select how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Hampshire County?
With Expedia's helpful filter tool, locating cheap cottages in Hampshire County has never been simpler. To find properties that are friendly on the wallet, narrow your search by amenities, budget and star rating.