A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
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In four months
Jan 1 - Jan 3

Top Cities in Hampshire County

A paved pathway flanked by red foliage and a wooden bridge.
CottagesCottages

Amherst

Amherst

Our top choices for Hampshire County cottages

A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

1. 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, (48 reviews)
"Great place, amazing lake!"
United States
megan g.
The price is CA $180
CA $458 total
includes taxes & fees
Sep 20 - Sep 21
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A wooden deck with a table and chairs, a window, and a view of the forest.

2. Cozy Becket Cottage Minutes from Lake Beaches

Cozy Becket Cottage Minutes from Lake Beaches
Sherwood Forest
9.0 out of 10, Wonderful, (4 reviews)
"It is a very cozy little cottage in a great location. The host was very responsive and the cottage overall clean. Wiould stay there again."
United States
Driss Z.
Cozy Becket Cottage Minutes from Lake Beaches
A stone building with a snow-covered roof and windows, surrounded by snow-laden bushes.

3. 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, (121 reviews)
"The Stone Schoolhouse was great! The perfect space upstairs. The location felt peaceful and remote while at the same time being close by everything you need. The hosts have done an excellent job of preserving the history of the building. I would recommend it as a place to stay for anyone planning a stay in the Berkshires"
United States
Alysia W.
Charming historic cottage on scenic road to Mt. Greylock
A deck with wicker furniture, a fire pit, and a view of a lake.

4. Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass
Otis
8.6 out of 10, Excellent, (10 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
A house with a brick chimney, a porch, and a grassy yard with two Adirondack chairs.

5. The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature
Cummington
10.0 out of 10, Exceptional, (228 reviews)
"Beautiful property and accommodations. "
United States
Matt D.
The Clearing - Quiet - Close To Nature
A cabin with a wooden deck, a staircase, and a small porch area.

6. 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!
A two-story house with a covered porch, surrounded by a lush green landscape and tall trees.

7. 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, (33 reviews)
"It was a great stay!"
United States
Joseph C.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
A rustic cabin with a stone foundation, a wooden exterior, and a chimney.

8. LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Monterey
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed a family vacation with our little dog at the lake! We chose the area to be close to extended family and found it to be perfect- comfortable house, beautiful clean lake and close to hiking, stores, and other activities."
United States
Abbey P.
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
A two-story house with a covered porch and a fire pit in the yard.

9. Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey
9.8 out of 10, Exceptional, (9 reviews)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
United States
Eric S.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
A deck with wicker furniture and a potted plant, surrounded by a wooden railing and a house with large windows.

10. 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

11. Massachusetts Vacation Rental w/ Deck

Massachusetts Vacation Rental w/ Deck
3.0 star property
Easthampton
Massachusetts Vacation Rental w/ Deck
A small, single-story house with a sloped roof, a front door, and two windows. It is surrounded by a grassy yard and trees.

12. Brimfield Waterfront cottage

Brimfield Waterfront cottage
Brimfield
10.0 out of 10, Exceptional, (22 reviews)
"The host was wonderful, location was perfectly distanced from Brimfield Flea Market, and the view from the porch was gorgeous! Lovely place to stay. "
United States
Jessica P.
Brimfield Waterfront cottage

13. Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.6 out of 10, Exceptional, (11 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
Trainmaster's Inn - Caboose
A lakeside property with a dock, a small boat, and a grassy area with a wooden deck.

14. Relax by the Lake - Cozy Lakefront Retreat with Scenic Views

Relax by the Lake - Cozy Lakefront Retreat with Scenic Views
Charlton
9.8 out of 10, Exceptional, (15 reviews)
"The place was great! We'd love to come back when it's warmer so we can take advantage of the water."
United States
Phil B.
Relax by the Lake - Cozy Lakefront Retreat with Scenic Views
A rustic cabin with a red exterior, a wooden deck, and a stone wall.

15. Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough
9.2 out of 10, Wonderful, (48 reviews)
"Could not have been more relaxing or enjoyable."
United States
Raymond B.
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

16. Brimfield Bungalow by the lake close to Sturbridge

Brimfield Bungalow by the lake close to Sturbridge
Brimfield
10.0 out of 10, Exceptional, (19 reviews)
"We had a great time staying in this home. It was very cozy and comfortable. The owner was very accommodating. I would stay here again!"
United States
Kara K.
Brimfield Bungalow by the lake close to Sturbridge
A single-story house with a front porch, a small staircase, and a white picket fence.

17. Cheerful 2 bedroom cottage with lake access close to Sturbridge line

Cheerful 2 bedroom cottage with lake access close to Sturbridge line
Brimfield
9.8 out of 10, Exceptional, (6 reviews)
"Clean and charming!"
United States
Delores L.
Cheerful 2 bedroom cottage with lake access close to Sturbridge line
A lakeside deck with a dock extending into the water, surrounded by trees and a grassy area with outdoor furniture.

18. Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
Holland
10.0 out of 10, Exceptional, (92 reviews)
"Stunning water view!"
United States
donna d.
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

19. Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!
Pittsfield
9.4 out of 10, Exceptional, (6 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!
A deck with a table and chairs, overlooking a lake with boats and a dock.

20. Picturesque Cottage with Sunroom on Ashmere Lake!

Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale
9.6 out of 10, Exceptional, (26 reviews)
"We will be back! Loved the peace and quiet, the relaxing deck, and use of kayaks. We had an amazing time!"
United States
Angela
Picturesque Cottage with Sunroom on Ashmere Lake!
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

The Ellery

The Ellery

10/10 Excellent
"Great location. Comfortable beds. Delicious breakfast. Very helpful staff."
Patricia 1-night trip
Posted 4 hours ago
The Ellery

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
571
Accommodation
124 Cottages
Lowest Price
CA $458
Highest Price
CA $458

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