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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Sandisfield vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,084 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is AED 347
AED 470 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
Property grounds

2. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,308 total
includes taxes & fees
23 Aug - 24 Aug
Big farmhouse in the foothills of the Berkshires
Outdoor spa tub

3. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 654
AED 1,539 total
includes taxes & fees
8 Sep - 9 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 380
AED 568 total
includes taxes & fees
31 Aug - 1 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 224
AED 1,104 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
TV

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 AED 1,223
AED 2,364 total
includes taxes & fees
1 Sep - 2 Sep
Treetop Hideaway in Tyringham
Terrace/patio

7. 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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 463
AED 885 total
includes taxes & fees
31 Aug - 1 Sep
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

8. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
7 Sep - 8 Sep
Cheerful 3-bedroom cottage with woodstove
TV, fireplace, printers

9. 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, (7 reviews)
"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
The price is AED 2,079
AED 4,874 total
includes taxes & fees
27 Aug - 28 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 992
AED 1,502 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Coffee/tea maker, fridge, microwave, oven

11. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is AED 3,359
AED 5,628 total
includes taxes & fees
23 Aug - 24 Aug
Renovated Downtown Great Barrington House
Interior

12. 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, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 617
AED 1,493 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

13. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is AED 419
AED 770 total
includes taxes & fees
19 Sep - 20 Sep
Peaceful Meadow Retreat
Interior

14. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,155 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Riverside Berkshires Retreat
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is AED 1,185
AED 2,074 total
includes taxes & fees
31 Aug - 1 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Outdoor dining

16. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AED 1,478
AED 2,334 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 828 total
includes taxes & fees
1 Sep - 2 Sep
Peaceful and cozy 1 bed 1 bath in quaint Winchester
4 bedrooms, travel crib, WiFi, bed sheets

18. 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 AED 1,868
AED 3,206 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape
Exterior

19. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is AED 336
AED 1,030 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Attic 10 min to Llitchfield
Beach nearby, sun loungers, beach towels

20. 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, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is AED 856
AED 1,317 total
includes taxes & fees
14 Sep - 15 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Excellent staff interaction. Great price and excellent location."
Irene 2-night trip
Posted 2 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 Tolland State Forest and Lake Garfield.

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.