Cottages in Hampshire County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Hampshire County cottages

House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!
3.0 star property
Becket
A-frame Cabin w/ Furnished Deck in Becket!
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

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!
House (3 Bedrooms) | Front of property

Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River
3.0 star property
Huntington
10.0 out of 10, Exceptional, (1 review)
"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
Exterior

Cavalier Cottage B&B

Cavalier Cottage B&B
3.0 star property
Shelburne Falls
9.0 out of 10, Wonderful, (2 reviews)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
United States
jennifer
Cavalier Cottage B&B
House (2 Bedrooms) | Interior

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.0 star property
Williamsburg
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (4 Bedrooms) | Front of property

Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres
3.0 star property
Royalston
10.0 out of 10, Exceptional, (2 reviews)
"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 (1 Bedroom) | Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
3.0 star property
Great Barrington
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
House (2 Bedrooms) | Interior

Sun-dappled Retreat - Walk to Wickaboag Lake!

Sun-dappled Retreat - Walk to Wickaboag Lake!
3.0 star property
West Brookfield
Sun-dappled Retreat - Walk to Wickaboag Lake!
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!
House (3 Bedrooms) | Interior

Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!
3.0 star property
Williamstown
Luxury Vacation Rental in the Berkshires!
House (3 Bedrooms) | Interior

Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Otis
Berkshires Cabin 2 Mi to Appalachian Trail!
House (5 Bedrooms) | Front of property

Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!
3.0 star property
Pittsfield
Spacious Historic Home in the Berkshires!
House (3 Bedrooms) | Front of property

Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay

Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay
3.0 star property
Housatonic
Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay
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
House (2 Bedrooms) | Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake!
3.0 star property
Stockbridge
2.0 out of 10, (1 review)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
House (2 Bedrooms) | Interior

Serene Riverfront Stay! 'the Mill River Cabin

Serene Riverfront Stay! 'the Mill River Cabin
3.0 star property
Mill River
Serene Riverfront Stay! 'the Mill River Cabin
House (1 Bedroom) | Interior

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
Charlemont
6.0 out of 10, (1 review)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
United States
Christopher
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (3 Bedrooms) | Interior

1 Mi to Dtwn: Beautiful Home in Williamstown!

1 Mi to Dtwn: Beautiful Home in Williamstown!
3.0 star property
Williamstown
1 Mi to Dtwn: Beautiful Home in Williamstown!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

Lakefront Granby Escape w/ Private Dock & Kayaks!
3.0 star property
Granby
Lakefront Granby Escape w/ Private Dock & Kayaks!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hampshire County Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"Loved it?"
Lisa 1-night trip
Posted 10 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
5
Accommodation
86 Cottages
Lowest Price
Highest Price

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.