Cottages in Hampshire County

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Top Cities in Hampshire County

Amherst Farm Winery is a small family owned winery offering an impressive list of fruity wines. We found this impressive old man on the grounds!
CottagesCottages

Amherst

Amherst

Compare 118 Cottages in Hampshire County with updated reviews, rates, and availability.

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (1)
"We were staying for an event in Adams and didn't need much... Stepping inside the cottage was a delight!! A great deal of thought and design has gone into making this little old lake cottage, into a lovely, friendly and comfortable place to stay. I hope we will have cause to return. "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (190)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

9.8 out of 10, Exceptional, (25)
"House and property were beautiful, well stocked and perfectly situated close to everything but also quiet and scenic. Owner was fantastic to deal with. She was helpful and accommodating, even had a sweet card and little gift to welcome us. Would definitely stay here again!! "
Cozy Berkshire cottage with fireplace.
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.2 out of 10, Wonderful, (5)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is AED 551
AED 1,219 total
includes taxes & fees
24 Jun - 25 Jun
Trainmaster's Inn - Caboose
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (109)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"2nd time here so I give it excellent review."
The price is AED 496
AED 967 total
includes taxes & fees
23 Jun - 24 Jun
Perfect Vacation Get Away - Historical New Marlborough
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard

10.0 out of 10, Exceptional, (1)
"Nice to have a Vrbo versus hotel in a quiet neighborhood. Heater wasn’t working and owner had someone there within a hour to fix it. We left our laptop and owner notified us immediately. Placed worked out great for our business trip."
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (2)
"This home is so adorable! Very clean. 4 bedrooms and 2 baths are a plus. Great location...beautiful view of the lake. "
Lake Views & Dock Access - Pittsfield Cottage!
Beachwood Cottage
Fridge, microwave, stovetop, coffee/tea maker

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"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."
Beachwood Cottage
Entire cottage in Berkshire Villiage
Books, stereo

Entire cottage in Berkshire Villiage

3.0 star property
9.4 out of 10, Exceptional, (3)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Interior

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.8 out of 10, Exceptional, (13)
"Just a nice lake house!!"
The price is AED 551
AED 1,305 total
includes taxes & fees
21 Jul - 22 Jul
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Brimfield Waterfront cottage
Property grounds

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (4)
"Warm and cozy. It was so nice to sit out on the porch with a complimetary bottle of wine and cookies from our host. He came to make sure we got into the home. It was very kind and thoughtful. Great location. We would love to stay here again. Highly recommend this cottage. "
Brimfield Waterfront cottage
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (108)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Grandparent’s Cottage 250 steps to the lake
Living area

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Property grounds

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is AED 4,087
AED 6,822 total
includes taxes & fees
25 Jun - 26 Jun
Berkshires farm, 30+ guests, 50 acres
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
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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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?
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