Cottages in Hampshire County

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

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, (34 reviews)
"Great location, beautiful view completely relaxing "
United States
Carlos T.
The price is AED 364
AED 1,053 total
includes taxes & fees
30 Apr - 1 May
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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, (22 reviews)
"This cottage was so cozy! So close to Great Barrington too. Loved being in the woods and hearing the trees. The place was clean and the owner answered questions quickly. We will definitely be back!"
United States
Aaron B.
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, (14 reviews)
"Wonderful place. Would stay, again!"
United States
Kristi B.
Brimfield Waterfront cottage
Exterior

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, (8 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, (212 reviews)
"Beautiful property and accommodations. "
United States
Matt D.
The Clearing - Quiet - Close To Nature
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
The price is AED 661
AED 1,070 total
includes taxes & fees
22 Apr - 23 Apr
Brookside cottage near the mountains and outdoor recreation
Exterior

2-bedroom cottage close to skiing with gas fireplace

2-bedroom cottage close to skiing with gas fireplace
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 skiing with gas fireplace
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
House (3 Bedrooms) | Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

Westfield Vacation Rental w/ Porch, Pets Welcome!
3.0 star property
Westfield
Westfield Vacation Rental w/ Porch, Pets Welcome!
Outdoor dining

Massachusetts Vacation Rental w/ Deck

Massachusetts Vacation Rental w/ Deck
3.0 star property
Easthampton
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

3 Mi to Dtwn Springfield: Winter Retreat w/ Office

3 Mi to Dtwn Springfield: Winter Retreat w/ Office
3.0 star property
Forest Park
3 Mi to Dtwn Springfield: Winter Retreat w/ Office
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)
"Area on the Lake was great. We really enjoyed the outdoor space and the deck. We were allowed to bring our dog which was a bonus. The house was fine but a little dust that i just cleaned up with supplies in the house. The large sun room window was excellent for watching the action on the lake."
United States
Paul N.
Private Island - Largest Fresh Water Reservoir in Mass
Living area

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
Amherst
Beautiful 2-bedroom cottage on Robert Frost Trail
Property grounds

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
Holland
10.0 out of 10, Exceptional, (86 reviews)
"Great stay beautiful property"
United States
Blake B.
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
Exterior

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
Beachwood Cottage
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
Terrace/patio

Waterfront Cottage 10 Min From Great Barrington

Waterfront Cottage 10 Min From Great Barrington
New Marlborough
10.0 out of 10, Exceptional, (100 reviews)
"Beautiful house and beautiful view. Loved all the tissues! Clean, warm and cozy space. Everything we needed. We’ll be back. "
United States
Matthew P.
Waterfront Cottage 10 Min From Great Barrington
Exterior

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Monterey
10.0 out of 10, Exceptional, (1 review)
"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

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AED 3,640
AED 6,600 total
includes taxes & fees
4 May - 5 May
Berkshires farm, 30+ guests, 50 acres
House (4 Bedrooms) | Interior

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
3.0 star property
Charlemont
10.0 out of 10, Exceptional, (1 review)
"Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which was a bit too firm! Would definitely rent here again "
United States
Amy
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"This is a quiet location, close to the airport. I've stayed here multiple times, the staff has always been very helpful. "
Arthur Edward Ouimet 1-night trip
Posted 1 hour ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Frequently asked questions

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How can I find cheap cottages in Hampshire County?
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