Cottages in Hampshire County

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Cottages in Hampshire County

Our top choices for Hampshire County cottages

Massachusetts Vacation Rental w/ Deck
Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

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!
Front of property

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
Historic Huntington Home - Walk to Westfield River
Private kitchen

Historic Huntington Home - Walk to Westfield River

3.0 star property
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."
Historic Huntington Home - Walk to Westfield River
Historic Home w/ Modern Updates on < 4 Acres
Interior

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
Charlemont Retreat on Chickley River w/ EV Charger
Interior

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
Quaint Massachusetts Home w/ Yard & Grill!
Interior

Quaint Massachusetts Home w/ Yard & Grill!

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

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Spacious Historic Home in the Berkshires!
Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Granby Escape w/ Private Dock & Kayaks!
Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Interior

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

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

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ 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.
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

Find out more about Hampshire County

Find out more about Hampshire County

Hampshire County Cottages information

Number of reviews
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?
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.