Cottages in Hampshire County

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Featured Cottages in Hampshire County

Outdoor dining
Massachusetts Vacation Rental w/ Deck

Massachusetts Vacation Rental w/ Deck

3.0 star property
Easthampton
Massachusetts Vacation Rental w/ Deck
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!
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)
"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!
Interior
Cozy Springfield Vacation Rental Near Downtown

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Forest Park
Cozy Springfield Vacation Rental Near Downtown
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)
"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
Exterior
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!
Interior
Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Windsor
Massachusetts Vacation Rental w/ Deck & Grill
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!
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)
"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
Interior
Quaint Massachusetts Home w/ Yard & Grill!

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Gill
Quaint Massachusetts Home w/ Yard & Grill!
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)
"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
Interior
Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!

3.0 star property
Williamstown
Luxury Vacation Rental in the Berkshires!
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)
"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
Terrace/patio
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Lee
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Interior
Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge
Stockbridge Home: Walk to Town Beach!
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!
Interior
Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!

3.0 star property
Pittsfield
Spacious Historic Home in the Berkshires!
Front of property
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)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"Yes"
lorraine 1-night trip
Posted 23 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
5
Accommodation
84 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?
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