Sandisfield, MA Vacation Homes from AED 746

A forested mountain range with autumn foliage.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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 Sandisfield vacation homes

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

1. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

AED 1,223 total

includes taxes & fees

3 Nov - 4 Nov

A hot tub with a string of lights above it, set against a dark night sky.

2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

AED 1,396 total

includes taxes & fees

12 Oct - 13 Oct

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

AED 1,426 total

includes taxes & fees

14 Oct - 15 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

4. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

AED 2,085 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Great Barrington

HEATHER G.

AED 1,277 total

includes taxes & fees

13 Oct - 14 Oct

A wooden cabin interior with a bench, a rug, and a hanging plant.

6. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

Thomas C.

AED 774 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

7. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

AED 1,618 total

includes taxes & fees

12 Oct - 13 Oct

A house with a porch, a garden with pink flowers, and a stone wall along the road.

8. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

AED 1,281 total

includes taxes & fees

12 Oct - 13 Oct

A staircase with a wooden handrail and a white wall with a light switch.

9. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

AED 1,128 total

includes taxes & fees

26 Oct - 27 Oct

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

AED 1,288 total

includes taxes & fees

13 Oct - 14 Oct

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

11. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mark M.

AED 2,577 total

includes taxes & fees

19 Oct - 20 Oct

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

12. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

AED 3,206 total

includes taxes & fees

18 Oct - 19 Oct

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

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

Great Barrington

Roberta

AED 4,879 total

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a sofa, armchair, coffee table, and TV.

14. Spacious Central Berkshires Home for Groups

Lee

Beth S.

AED 2,168 total

includes taxes & fees

12 Oct - 13 Oct

A spacious kitchen with a large island, wooden beams, and pendant lighting.

15. Linny's - Private Dock - Lake Access - Firepit

West Suffield

Patricia S.

A living room with a sofa, armchairs, a coffee table, and a television.

16. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

AED 2,325 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

17. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."

Margaret A.

AED 746 total

includes taxes & fees

20 Oct - 21 Oct

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

18. Sun Filled Lake House Living

Avon

Joseph C.

AED 983 total

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a front porch, surrounded by lush greenery and trees.

19. Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

Annetta D.

AED 2,630 total

includes taxes & fees

11 Oct - 12 Oct

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

20. Ellie’s Overlook, best view in the Berkshires!

Richmond

AED 2,538 total

includes taxes & fees

14 Oct - 15 Oct

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Sandisfield Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sandisfield vacation homes

1. Real Estate: Therapy - Lake, Laundry, Love it

2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing