Cottages in Hampshire County

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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Hampshire County

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

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Westfield Vacation Rental w/ Porch, Pets Welcome!
Stylish single-story home with a gabled roof and a cozy front porch.

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Sun-dappled Retreat - Walk to Wickaboag Lake!
Enjoy cooking in this well-lit kitchen with ample counter space and a central island.

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!
Historic Huntington Home - Walk to Westfield River
Kitchen features a large window, refrigerator, stove, and dishwasher, with a ceiling fan for ventilation.

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Charlemont Retreat on Chickley River w/ EV Charger
Enjoy the serene surroundings and well-maintained deck adjacent to this house.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
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...
Charlemont Retreat on Chickley River w/ EV Charger
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cozy cabin with a fireplace, dining area, and forest views.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Historic Home w/ Modern Updates on < 4 Acres
Cozy retreat with a large bed, nightstand, and dresser, offering a view of the outdoors.

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
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). "
Cavalier Cottage B&B
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Lakefront Granby Escape w/ Private Dock & Kayaks!
Cozy living room with a fireplace, sofa, and coffee table, surrounded by rustic charm.

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Relax on the porch amidst a serene garden and wooded surroundings, complete with a cozy fireplace.

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

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Relax in a serene garden setting surrounded by mature trees and lush greenery, with a stone fire pit and Adirondack chairs.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
House (2 Bedrooms) | Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (1 Bedroom) | Front of property

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

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Luxury Vacation Rental in the Berkshires!
Enjoy cooking in this well-equipped kitchen with a range hood, double oven, and granite countertop.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cottage (1 Bedroom) | Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Stockbridge Home: Walk to Town Beach!
House (3 Bedrooms) | Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
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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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.