Search Vacation Homes in Sandisfield

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In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Sandisfield vacation homes

Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$429 nightly
The price is $486
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$613 nightly
The price is $628
Dec 28 - Dec 29
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Home in Great Barrington
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Dec 22 - Dec 23
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$346 nightly
The price is $387
Dec 22 - Dec 23
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Smart TV, fireplace
Sun Filled Lake House Living

Sun Filled Lake House Living

Sun Filled Lake House Living
2.0 star property
Avon
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
$244 nightly
The price is $258
Jan 7 - Jan 8, 2026
Total with taxes and fees
Sun Filled Lake House Living
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
$339 nightly
The price is $358
Dec 22 - Dec 23
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Private kitchen
Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
2.0 star property
Torrington
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$450 nightly
The price is $503
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
Goshen
$450 nightly
The price is $510
Dec 21 - Dec 22
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
$424 nightly
The price is $480
Dec 29 - Dec 30
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Game room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 21 - Dec 22
Total with taxes and fees
Family Ski Getaway in the Berkshires
Property grounds
3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
$281 nightly
The price is $314
Jan 12 - Jan 13, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley
Millerton
10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
$486 nightly
The price is $550
Dec 22 - Dec 23
Total with taxes and fees
Modern Ranch Retreat in Hudson Valley
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$496 nightly
The price is $554
Jan 4 - Jan 5, 2026
Total with taxes and fees
Great Barrington Get Away
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
$1,193 nightly
The price is $1,332
Dec 21 - Dec 22
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Hillsdale
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
$1,125 nightly
The price is $1,260
Jan 19 - Jan 20, 2026
Total with taxes and fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$524 nightly
The price is $585
Dec 21 - Dec 22
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$1,071 nightly
The price is $1,214
Dec 21 - Dec 22
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
$1,587 nightly
The price is $1,773
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
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 Sandisfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Spacious room and loved pool and hot tub!"
Deanna 5-night trip
Posted 1 day ago
Berkshire Mountain Lodge

Find out more about Sandisfield

Sandisfield Vacation Homes information

Number of reviews
327
Accommodation
384 Vacation Homes
Lowest Price
$257
Highest Price
$1,773

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