Cottages in Hampshire County

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cottages in Hampshire County

The Clearing - Quiet - Close To Nature
Exterior

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (203)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature
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, (25)
"This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!"
The price is AED 430
AED 1,136 total
includes taxes & fees
5 Oct - 6 Oct
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, (10)
"The cabin was definitely cozy, the treats were a nice addition, and the kitchen had most of what we needed. Would return next time we plan to be in the area. Gus was great to communicate with! Thank you@"
Brimfield Waterfront cottage
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Outdoor dining

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

10.0 out of 10, Exceptional, (3)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Charming historic cottage on scenic road to Mt. Greylock
Exterior

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (115)
"What a lovely property! And Rich was just terrific!"
Charming historic cottage on scenic road to Mt. Greylock
Light-filled cottage
Exterior

Light-filled cottage

10.0 out of 10, Exceptional, (1)
"Beautiful, well-designed home deserves a 10 out of 10 for aesthetics. Very glad Jing (the host) and her family are sharing this jewel of a home with the rest of us. Jing was a quick, kind and cordial communicator. The house location was quiet and tranquil. Nearby lake was within walking distance and delightful."
Light-filled cottage
Massachusetts Vacation Rental w/ Deck
Outdoor dining

Massachusetts Vacation Rental w/ Deck

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

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.6 out of 10, Exceptional, (8)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is AED 551
AED 1,204 total
includes taxes & fees
5 Oct - 6 Oct
Trainmaster's Inn - Caboose
Westfield Vacation Rental w/ Porch, Pets Welcome!
House (3 Bedrooms) | Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
Exterior

Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

10.0 out of 10, Exceptional, (86)
"The home was cozy and comfortable. Very peaceful, tranquil location. Felt like we were the only ones on the lake. I highly recommend!"
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
Sun-dappled Retreat - Walk to Wickaboag Lake!
House (2 Bedrooms) | Front of property

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
House (3 Bedrooms) | Front of property

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
Historic Huntington Home - Walk to Westfield River
Historic Home w/ Modern Updates on < 4 Acres
House (4 Bedrooms) | Interior

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Cozy Springfield Vacation Rental Near Downtown
House (3 Bedrooms) | Interior

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 out of 10, Exceptional, (15)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Charlemont Retreat on Chickley River w/ EV Charger
House (4 Bedrooms) | Interior

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
Entire cottage in Berkshire Villiage
Exterior

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (7)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Quaint Massachusetts Home w/ Yard & Grill!
House (2 Bedrooms) | Interior

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is AED 3,471
AED 6,150 total
includes taxes & fees
3 Nov - 4 Nov
Berkshires farm, 30+ guests, 50 acres
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

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

10/10 Excellent
"Clean rooms, great breakfast and really nice staff! "
Cecile 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Frequently asked questions

Why book your cottage in Hampshire County with Expedia?
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How can I find cheap cottages in Hampshire County?
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