Cottages in Hampshire County

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Top Cities in Hampshire County

Cottages in Hampshire County

Cottage in Cummington

10.0 out of 10, Exceptional, (210)
"Very clean home. Grounds and pool are beautiful. My family and I enjoyed a relaxing weekend "
United States
Kimberly P.
The Clearing - Quiet - Close To Nature

Cottage in New Marlborough

9.6 out of 10, Exceptional, (18)
"Lovely cottage. Great for 2 couples. Lots of privacy for each but comfy gathering spots for dining and relaxing. Host was very responsive to questions. Great stay!"
United States
Lisa T.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Cottage in Stafford

9.8 out of 10, Exceptional, (29)
"FANTASTIC STAY! there was an issue after arrival that was QUICKLY addressed... rest of stay was amazing! Beautiful home. Great kayaks.. lots of fishing!QUICK AND PLEASANT COMMUNICATIONS.THANK YOU!!!"
United States
Michelle O.
The price is AED 430
AED 1,147 total
includes taxes & fees
8 Dec - 9 Dec
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Cottage in New Marlborough

10.0 out of 10, Exceptional, (99)
"very comfortable, great location on the lake, and near good hiking and nice towns"
United States
John M.
Waterfront Cottage 10 Min From Great Barrington

Cottage in Easthampton

3.0 star property
Massachusetts Vacation Rental w/ Deck

Cottage in Palmer

9.6 out of 10, Exceptional, (9)
"This place is a unique stay, that's for sure! If you are looking for an unforgettable experience, you should come. If you love trains, you should come. However, if you are not that fond of tight spaces or old-fashioned style and your traveling companions are looking for luxury and privacy, you might want to look elsewhere. The bathroom is a big tight (it's a caboose bathroom). But the location is really fun. And the owners are very accommodating! "
United States
Lisa B.
The price is AED 551
AED 1,165 total
includes taxes & fees
1 Dec - 2 Dec
Trainmaster's Inn - Caboose

Cottage in Otis

8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass

Cottage in Holland

10.0 out of 10, Exceptional, (86)
"We had a wonderful time. The cottage was super clean and exactly as advertised. The view of the lake from the front slider was beautiful. The water was very clean and we went swimming and kayaking every day. The sandy beach made it very easy to get into the water. Our Golden Retriever, Sunny, loved swimming and chasing the minnows by the shore. We enjoyed the local restaurants and.the seafood at the Maine Attraction was great.. We wished we could have stayed longer and plan to come back again...
United States
Bill K.
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!

Cottage in Westfield

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

Cottage in Charlemont

3.0 star property
10.0 out of 10, Exceptional, (1)
"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!

Cottage in Brimfield

10.0 out of 10, Exceptional, (13)
"Property is in excellent condition, just the right amount of space for us. "
United States
earl p.
Brimfield Waterfront cottage

Cottage in Forest Park

3.0 star property
Cozy Springfield Vacation Rental Near Downtown

Cottage in Royalston

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors."
United States
Melissa
Historic Home w/ Modern Updates on < 4 Acres

Cottage in West Brookfield

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

Cottage in Charlton

10.0 out of 10, Exceptional, (6)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
United States
michael C.
Cozy Lakefront Escape — Private and Relaxing with Scenic Views

Cottage in Lanesboro

10.0 out of 10, Exceptional, (118)
"Comfortable, unique, great hosts, and a perfect location!"
United States
Isabel A.
Charming historic cottage on scenic road to Mt. Greylock

Cottage in Windsor

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill

Cottage in Great Barrington

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Cottage in Huntington

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."
United States
Thomas
Historic Huntington Home - Walk to Westfield River

Cottage in New Marlborough

7.4 out of 10, Good, (3)
"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."
United States
Brenda A.
Light-filled cottage
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

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.