A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Vacation Homes in Hampshire County

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Hampshire County vacation homes

1. Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
Goshen
9.6 out of 10, Exceptional, (25 reviews)
"This is a magical stay!"
United States
Ryan B.
Experience Three Sisters Sanctuary in Goshen, MA

2. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is AED 562
AED 677 total
includes taxes & fees
4 Nov - 5 Nov
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is AED 562
AED 874 total
includes taxes & fees
4 Nov - 5 Nov
Lovely 2nd Floor Apartment

4. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is AED 739
AED 1,453 total
includes taxes & fees
15 Nov - 16 Nov
Shelburne Falls on Main

5. Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room
Stephentown
10.0 out of 10, Exceptional, (1 review)
"Our family enjoyed our fall trip here."
United States
Aamina A.
Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

6. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AED 744
AED 1,052 total
includes taxes & fees
4 Nov - 5 Nov
Leaf-Peeper Paradise in the Berkshires

7. Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Spencer
10.0 out of 10, Exceptional, (215 reviews)
"Christine the owner is the perfect host. The rental is a perfect place to just get away and relax by the lake. Everything you could possibly need is there. Will definitely be heading back there for another getaway."
United States
GALE L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

8. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (155 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AED 727
AED 1,270 total
includes taxes & fees
4 Nov - 5 Nov
Big farmhouse in the foothills of the Berkshires

9. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was fantastic. Check in was super smooth and the host was very responsive. I would definitely stay here again in the future."
United States
Nicholas T.
The price is AED 661
AED 1,371 total
includes taxes & fees
4 Nov - 5 Nov
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

10. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is AED 598
AED 683 total
includes taxes & fees
4 Nov - 5 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

11. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.8 out of 10, Exceptional, (12 reviews)
"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"
United States
John
The price is AED 569
AED 1,270 total
includes taxes & fees
4 Nov - 5 Nov
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

12. Adorable 3-bedroom 2-bath House in quiet, safe, kid/pet friendly neighborhood.

Adorable 3-bedroom 2-bath House in quiet, safe, kid/pet friendly neighborhood.
Enfield
9.8 out of 10, Exceptional, (8 reviews)
"The perfect stay for our weekend trip. Easy check in and clean space. Good for kids to play in the fenced in back yard. We had a great stay! "
United States
Carly G.
Adorable 3-bedroom 2-bath House in quiet, safe, kid/pet friendly neighborhood.

13. Hilltop Escape with Views & Hot Tub

Hilltop Escape with Views & Hot Tub
New Marlborough
10.0 out of 10, Exceptional, (5 reviews)
"Amazing home. Beautifully and comfortably appointed"
United States
Theresa W.
Hilltop Escape with Views & Hot Tub

14. 3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC
Pine Point
9.4 out of 10, Exceptional, (13 reviews)
"Nice quiet stay, manager was very communicative and even came over quickly and let us in when we locked ourselves out."
United States
Bert S.
3-bedroom house in perfect Springfield with WiFi, AC

15. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.8 out of 10, Excellent, (25 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is AED 735
AED 1,459 total
includes taxes & fees
26 Nov - 27 Nov
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

16. Beautiful retreat in a lake community to the enjoy the summer season.

Beautiful retreat in a lake community to the enjoy the summer season.
Tolland
10.0 out of 10, Exceptional, (59 reviews)
"Everything about this home was great for a get away weekend with peace and quite."
United States
Barbara A.
Beautiful retreat in a lake community to the enjoy the summer season.

17. Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course
Williamstown
10.0 out of 10, Exceptional, (29 reviews)
"A unique, beautiful home with amazing views of Williamstown and the mountains beyond. A relaxing family getaway!"
United States
Robin A.
Contemporary Berkshire Home with Views of Taconic Golf Course

18. Leaves are turning and wish you were watching! Warm days, cool nights weather.

Leaves are turning and wish you were watching! Warm days, cool nights weather.
Charlemont
10.0 out of 10, Exceptional, (29 reviews)
"Our stay was perfect! It was centrally located for our needs. We would stay again our next trip to that area."
United States
Lynn T.
Leaves are turning and wish you were watching! Warm days, cool nights weather.

19. Sunny, vintage farmhouse in the center of quintessential New England farm town.

Sunny, vintage farmhouse in the center of quintessential New England farm town.
Granby
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay at the farmhouse. "
United States
Karen C.
Sunny, vintage farmhouse in the center of quintessential New England farm town.

20. RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes

RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes
Hancock
10.0 out of 10, Exceptional, (1 review)
"Terrific place. Great location to launch from in the summer time to do sight seeing throughout the area. Quiet and peaceful spot to begin and end days. Well appointed, newly updated, very comfortable. Host provided timely communications. Easy check in and check out. Would definitely stay again!"
United States
Joseph S.
RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes
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

Top Hampshire County Hotel Reviews

Explore a world of travel with Expedia