Cottages in Hampshire County

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Hampshire County cottages

Outdoor dining

Cottage in Easthampton

Massachusetts Vacation Rental w/ Deck
3.0 star property
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Cottage in Westfield

Westfield Vacation Rental w/ Porch, Pets Welcome!
3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
House (4 Bedrooms) | Interior

Cottage in Charlemont

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
3.0 star property
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

Cottage in Forest Park

3 Mi to Dtwn Springfield: Winter Retreat w/ Office
3.0 star property
3 Mi to Dtwn Springfield: Winter Retreat w/ Office
House (4 Bedrooms) | Interior

Cottage in Royalston

Historic Home w/ Modern Updates on < 4 Acres
3.0 star property
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

Cottage in West Brookfield

Sun-dappled Retreat - Walk to Wickaboag Lake!
3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!
House (4 Bedrooms) | Interior

Cottage in Windsor

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

Cottage in Great Barrington

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
House (3 Bedrooms) | Front of property

Cottage in Huntington

Historic Huntington Home - Walk to Westfield River
3.0 star property
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

Cottage in Gill

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

Cottage in Charlemont

Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
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

Cottage in Williamstown

Luxury Vacation Rental in the Berkshires!
3.0 star property
Luxury Vacation Rental in the Berkshires!
House (5 Bedrooms) | Interior

Cottage in Whitingham

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Exterior

Cottage in Shelburne Falls

Cavalier Cottage B&B
3.0 star property
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

Cottage in Lee

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
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

Cottage in Stockbridge

Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
House (2 Bedrooms) | Interior

Cottage in Becket

A-frame Cabin w/ Furnished Deck in Becket!
3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
House (5 Bedrooms) | Front of property

Cottage in Pittsfield

Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Cottage (4 Bedrooms) | Interior

Cottage in Glendale

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
3.0 star property
10.0 out of 10, Exceptional, (1 review)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
House (2 Bedrooms) | Interior

Cottage in Granby

Lakefront Granby Escape w/ Private Dock & Kayaks!
3.0 star property
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?
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.