Cottages in Hampshire County

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Hampshire County cottages

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 (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

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 (4 Bedrooms) | Interior

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
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

Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill
3.0 star property
Windsor
Massachusetts Vacation Rental w/ Deck & Grill
House (4 Bedrooms) | Interior

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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
House (2 Bedrooms) | Interior

Quaint Massachusetts Home w/ Yard & Grill!

Quaint Massachusetts Home w/ Yard & Grill!
3.0 star property
Gill
Quaint Massachusetts Home w/ Yard & Grill!
House (4 Bedrooms) | Interior

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
Charlemont
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Stacy
Charlemont Retreat on Chickley River w/ EV Charger
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 (5 Bedrooms) | Interior

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Whitingham
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
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 (5 Bedrooms) | Front of property

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Lee
10.0 out of 10, Exceptional, (1 review)
"What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character."
United States
Mary
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
House (3 Bedrooms) | Interior

Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge
Stockbridge Home: Walk to Town Beach!
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!
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!
Cottage (4 Bedrooms) | Interior

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
3.0 star property
Glendale
10.0 out of 10, Exceptional, (1 review)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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.
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Top Hampshire County Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Stayed for nye. Great time. "
Shannon 1-night trip
Posted 2 days ago
Wellsworth Hotel

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
5
Accommodation
85 Cottages
Lowest Price
Highest Price

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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