A forested mountain range with autumn foliage.

Sandisfield Vacation Rentals

  • 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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Sandisfield vacation rentals

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

1. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is ￥25,297
￥31,784 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Camper tucked into the woods
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

2. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is ￥38,688
￥89,076 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Cottage-Sunset On The Lake
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,175 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is ￥13,532
￥18,641 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

4. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"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!! "
United States
Samantha G.
The price is ￥43,267
￥89,631 total
includes taxes & fees
Nov 4 - Nov 5
Treetop Hideaway in Tyringham
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.

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,023
￥59,053 total
includes taxes & fees
Oct 7 - Oct 8
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

6. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (54 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is ￥19,897
￥37,567 total
includes taxes & fees
Oct 8 - Oct 9
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,297
￥60,006 total
includes taxes & fees
Oct 13 - Oct 14
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥13,738
￥52,386 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A sandy beach with a lake and forest in the background.

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is ￥32,991
￥51,838 total
includes taxes & fees
Oct 12 - Oct 13
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥35,103
￥54,908 total
includes taxes & fees
Oct 13 - Oct 14
Home in Great Barrington
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

11. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.6 out of 10, Excellent, (7 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is ￥14,207
￥22,041 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 1-bedroom studio in serene Great Barrington with AC
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

12. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥29,419
￥69,550 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
A staircase with a wooden handrail and a white wall with a light switch.

13. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 ￥32,119
￥50,163 total
includes taxes & fees
Oct 7 - Oct 8
Leaf-Peeper Paradise in the Berkshires
A house with a porch, a garden with pink flowers, and a stone wall along the road.

14. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great location"
United States
Will G.
The price is ￥29,213
￥55,080 total
includes taxes & fees
Oct 12 - Oct 13
Big farmhouse in the foothills of the Berkshires
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥21,792
￥37,930 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥64,111
￥110,769 total
includes taxes & fees
Oct 19 - Oct 20
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥31,570
￥55,541 total
includes taxes & fees
Oct 21 - Oct 22
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern living room with a sofa, armchair, coffee table, and TV.

18. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is ￥46,189
￥93,219 total
includes taxes & fees
Oct 12 - Oct 13
Spacious Central Berkshires Home for Groups
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

19. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is ￥80,297
￥137,846 total
includes taxes & fees
Oct 18 - Oct 19
Stylish Mid-century Modern Berkshires Cape
A wooden cabin with a porch, a grill, and a flower planter.

20. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥31,570
￥59,932 total
includes taxes & fees
Oct 7 - Oct 8
Ideal location for summer and winter activities with plenty of outdoor space.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sandisfield Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"
F. Cole 1-night trip
Posted 3 hours ago
The Cornell Inn, Lenox & The Berkshires

Find out more about Sandisfield

Search for holiday rentals in Sandisfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Sandisfield using one of the methods below:

  • View our selection of featured holiday rentals in Sandisfield
  • Use the map to find apartments and other holiday homes in the Sandisfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sandisfield while they last

Look no further and take a look at our great range of rental properties in Sandisfield!

Frequently asked questions

Can I find a vacation rental in Sandisfield?

Yes, we offer vacation rentals close to well known attractions in Sandisfield, or you can select a more remote option if you want a relaxing place to stay. Sandisfield is known for its forests and aquarium. Make sure you have time to check out the spas while you're in the area.

What are some of the best vacation rentals that Sandisfield has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: Visitors like this Sandisfield vacation home rental. It is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Sandisfield?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Sandisfield stay.

What can I see and do in Sandisfield?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Cookson State Forest. In the larger area, you’ll find Lake Garfield and Otis Reservoir.

What are vacation rentals like in Sandisfield?

Vacation rentals are privately owned properties you can book for several days or more in Sandisfield. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.