A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Hillsdale holiday homes

Exterior

1. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is HK$2,153
HK$4,107 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
TV

2. 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 HK$2,589
HK$5,025 total
includes taxes & fees
2 Sept - 3 Sept
Treetop Hideaway in Tyringham
Smart TV, books

3. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,542
HK$4,951 total
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups
Smart TV

4. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,673
HK$3,543 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
4 bedrooms, travel cot, WiFi, bed sheets

5. 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 HK$3,989
HK$6,848 total
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
Outdoor dining

6. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,464
HK$4,347 total
includes taxes & fees
9 Aug - 10 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

7. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
Stockbridge In-town Escape
Coffee/tea maker, fridge, microwave, oven

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (37 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$2,266
HK$3,390 total
includes taxes & fees
10 Aug - 11 Aug
Home in Great Barrington
3 bedrooms, iron/ironing board, WiFi, bed sheets

9. 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 HK$3,444
HK$5,599 total
includes taxes & fees
7 Sept - 8 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

10. 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 HK$1,765
HK$2,681 total
includes taxes & fees
8 Sept - 9 Sept
Cozy Riverside Berkshires Retreat
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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 HK$1,373
HK$2,497 total
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
TV, fireplace, printers

12. 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 HK$4,462
HK$10,452 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining

13. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$5,757
HK$10,065 total
includes taxes & fees
10 Aug - 11 Aug
Hancock Village Inn Near Jiminy Peak
Exterior

14. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is HK$2,110
HK$4,355 total
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Coffee/tea maker, fridge, microwave, oven

15. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is HK$549
HK$1,614 total
includes taxes & fees
9 Aug - 10 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
TV, DVD player, books, video library

16. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is HK$981
HK$2,142 total
includes taxes & fees
10 Aug - 11 Aug
1800s Carriage house in Berkshires / Hudson Valley
Interior

17. The entire Stephentown Hotel! 28 person occupancy

The entire Stephentown Hotel! 28 person occupancy
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Great property"
United States
Peter T.
The price is HK$9,060
HK$15,183 total
includes taxes & fees
13 Aug - 14 Aug
The entire Stephentown Hotel! 28 person occupancy
Coffee/tea maker, fridge, microwave, stovetop

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,381
HK$4,397 total
includes taxes & fees
9 Aug - 10 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Outdoor dining

19. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is HK$2,165
HK$4,445 total
includes taxes & fees
8 Sept - 9 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
Coffee/tea maker, fridge, microwave, oven

20. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,982
HK$11,554 total
includes taxes & fees
17 Aug - 18 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
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 Hillsdale Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Property is aging and needs attention. Still a nice place to stay."
James 4-night trip
Posted 5 hours ago
The Red Lion Inn

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
264
Accommodation
664 Vacation Homes
Lowest Price
HK$1,614
Highest Price
HK$15,183

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