
Vacation Homes in Hampshire County
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Our top choices for Hampshire County vacation homes

1. Experience Three Sisters Sanctuary in Goshen, MA
Experience Three Sisters Sanctuary in Goshen, MAGoshen
9.6 out of 10, Exceptional, (25 reviews)

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 8Brimfield
9.2 out of 10, Wonderful, (12 reviews)
The price is AED 562
AED 677 total
includes taxes & fees
4 Nov - 5 Nov

3. Lovely 2nd Floor Apartment
Lovely 2nd Floor ApartmentGreenfield
10.0 out of 10, Exceptional, (73 reviews)
The price is AED 562
AED 874 total
includes taxes & fees
4 Nov - 5 Nov

4. Shelburne Falls on Main
Shelburne Falls on MainShelburne Falls
10.0 out of 10, Exceptional, (1 review)
The price is AED 739
AED 1,453 total
includes taxes & fees
15 Nov - 16 Nov

5. Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room
Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game RoomStephentown
10.0 out of 10, Exceptional, (1 review)

6. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AED 744
AED 1,052 total
includes taxes & fees
4 Nov - 5 Nov

7. Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemoreSpencer
10.0 out of 10, Exceptional, (215 reviews)

8. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (155 reviews)
The price is AED 727
AED 1,270 total
includes taxes & fees
4 Nov - 5 Nov

9. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central ACBoston Road
9.0 out of 10, Wonderful, (14 reviews)
The price is AED 661
AED 1,371 total
includes taxes & fees
4 Nov - 5 Nov

10. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6Ware
9.8 out of 10, Exceptional, (27 reviews)
The price is AED 598
AED 683 total
includes taxes & fees
4 Nov - 5 Nov

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 RestaurantsSomers
9.8 out of 10, Exceptional, (12 reviews)
The price is AED 569
AED 1,270 total
includes taxes & fees
4 Nov - 5 Nov

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)

13. Hilltop Escape with Views & Hot Tub
Hilltop Escape with Views & Hot TubNew Marlborough
10.0 out of 10, Exceptional, (5 reviews)

14. 3-bedroom house in perfect Springfield with WiFi, AC
3-bedroom house in perfect Springfield with WiFi, ACPine Point
9.4 out of 10, Exceptional, (13 reviews)

15. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful SpringfieldBoston Road
8.8 out of 10, Excellent, (25 reviews)
The price is AED 735
AED 1,459 total
includes taxes & fees
26 Nov - 27 Nov

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)

17. Contemporary Berkshire Home with Views of Taconic Golf Course
Contemporary Berkshire Home with Views of Taconic Golf CourseWilliamstown
10.0 out of 10, Exceptional, (29 reviews)

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)

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)

20. RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes
RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to SlopesHancock
10.0 out of 10, Exceptional, (1 review)
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

Hotel UMass
8/10 Good
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