Cottages in Hampshire County

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Top Cities in Hampshire County

Cottages in Hampshire County

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"2nd time here so I give it excellent review."
The price is SAR 563
SAR 1,053 total
includes taxes & fees
31 Jul - 1 Aug
Perfect Vacation Get Away - Historical New Marlborough

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 SAR 563
SAR 1,302 total
includes taxes & fees
31 Jul - 1 Aug
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"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!

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

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming 2-bedroom Lakefront cottage - Near Treehouse Brewery

Charming 2-bedroom Lakefront cottage - Near Treehouse Brewery

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (192)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (110)
"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

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (6)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (3)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck

Trainmaster's Inn - Caboose

9.4 out of 10, Exceptional, (6)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is SAR 563
SAR 1,241 total
includes taxes & fees
15 Jul - 16 Jul
Trainmaster's Inn - Caboose

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....

Westfield Vacation Rental w/ Porch, Pets Welcome!

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

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"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

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

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is SAR 6,481
SAR 9,557 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires farm, 30+ guests, 50 acres

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
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?
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.