Search results; Over 1,000 homes in Middlefield

Home in Hinsdale
Sunny, Stylish Berkshire Mountain Retreat
5 beds
Aug 21 – 26
ﺩ.ﺇ10,332 for 5 nights
4.78 out of 5 average rating, 9 reviews
Guest favorite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 double beds
Sep 7 – 12
ﺩ.ﺇ4,107 for 5 nights
4.95 out of 5 average rating, 286 reviews
Top guest favorite
Home in Washington
Peaceful Retreat in the Berkshires
4 beds
Sep 9 – 14
ﺩ.ﺇ5,485 for 5 nights
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Guesthouse in Cummington
Clark Cottage
2 beds
Oct 5 – 10
ﺩ.ﺇ3,057 for 5 nights
5.0 out of 5 average rating, 117 reviews
Guest favorite
Guesthouse in Becket
Country Cabin
1 queen bed
Sep 3 – 8
ﺩ.ﺇ2,842 for 5 nights
4.93 out of 5 average rating, 277 reviews
Top guest favorite
Farm stay in Worthington
Like sleeping on a cloud
3 beds
Sep 3 – 8
ﺩ.ﺇ4,607 for 5 nights
4.98 out of 5 average rating, 40 reviews
Home in Hinsdale
Berkshire Lake-side Retreat
1 queen bed
Aug 31 – Sep 5
ﺩ.ﺇ3,746 for 5 nights
New place to stay
Home in Becket
Charming Home Nestled in the Berkshires
4 beds
Sep 2 – 7
ﺩ.ﺇ5,920 for 5 nights
4.81 out of 5 average rating, 69 reviews
Guest favorite
Home in Washington
Modern Berkshire Mountain Home
4 beds
Aug 19 – 24
ﺩ.ﺇ8,666 for 5 nights, originally ﺩ.ﺇ10,754
5.0 out of 5 average rating, 23 reviews
Superhost
Apartment in Chester
Quiet getaway in the Berkshires
3 double beds
Aug 31 – Sep 5
ﺩ.ﺇ2,312 for 5 nights
4.77 out of 5 average rating, 211 reviews
Top guest favorite
Cabin in Becket
WALK to lake! Dog friendly, Kayaks, A-Frame, Hike
Aug 24 – 29
ﺩ.ﺇ4,187 for 5 nights, originally ﺩ.ﺇ4,701
5.0 out of 5 average rating, 17 reviews
Guest favorite
Cottage in Becket
Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
6 beds
Sep 14 – 19
ﺩ.ﺇ4,056 for 5 nights, originally ﺩ.ﺇ4,634
4.93 out of 5 average rating, 230 reviews
Room in Washington
Stay with VeraNon-profit cancer,
Berkshires Oasis: 2nd Floor Wing (2 bedrooms)
Aug 18 – 23
ﺩ.ﺇ4,844 for 5 nights
Guest favorite
Apartment in Otis
Enjoy every season the Berkshires have to offer.
2 beds
Aug 24 – 29
ﺩ.ﺇ3,122 for 5 nights
4.95 out of 5 average rating, 111 reviews
Guest favorite
Home in Becket
Pristine Home In Becket Woods
5 beds
Aug 25 – 30
ﺩ.ﺇ6,126 for 5 nights, originally ﺩ.ﺇ6,834
4.9 out of 5 average rating, 42 reviews
Guest favorite
Home in Becket
Nerd Preservation Sanctuary
2 beds
Aug 24 – 29
ﺩ.ﺇ2,902 for 5 nights
4.96 out of 5 average rating, 85 reviews
Guest favorite
Home in Becket
Hot Tub, Canoe, Hike, Berkshires!
4 beds
Sep 28 – Oct 3
ﺩ.ﺇ3,689 for 5 nights, originally ﺩ.ﺇ4,242
4.98 out of 5 average rating, 64 reviews
Guest favorite
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
4 beds
Aug 24 – 29
ﺩ.ﺇ5,136 for 5 nights, originally ﺩ.ﺇ8,478
4.88 out of 5 average rating, 348 reviews