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

Cottages in Hampshire County

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Hampshire County cottages

Terrace/patio

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, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is HK$1,020
HK$2,574 total
includes taxes & fees
20 Sept - 21 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Outdoor dining

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
Exterior

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
Outdoor dining

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
Exterior

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
Exterior

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!
Exterior

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!
Exterior

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
Exterior

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
Terrace/patio

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
Outdoor dining

11. Massachusetts Vacation Rental w/ Deck

Massachusetts Vacation Rental w/ Deck
3.0 star property
Easthampton
Massachusetts Vacation Rental w/ Deck
Exterior

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
Interior

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
Exterior

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
Exterior

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!
Exterior

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
Exterior

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
Property grounds

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!
Exterior

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!
Outdoor dining

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

Wellsworth Hotel

Wellsworth Hotel

8/10 Good
"The hotel was built in a former optical factory and the exterior is quite unique and beautiful. Unfortunately the interior seems to have lost most of its charm during this transformation and it generally felt a bit dated (very early 2000s vibe) and perhaps a bit past its heyday. That being said, the staff was pleasant, it seemed fairly well maintained and clean, and the pool and fitness center were nice amenities. It is also only a 25-30 minute drive to Brimfield, so a nice location if you’re coming to the antique market."
Laura 4-night trip
Posted less than an hour ago
Wellsworth Hotel

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
620
Accommodation
123 Cottages
Lowest Price
HK$2,574
Highest Price
HK$2,574

Frequently asked questions

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