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

Hillsdale Vacation Rentals

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Check prices for these dates

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

Our top choices for Hillsdale vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

1. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is ￥23,771
￥30,173 total
includes taxes & fees
Aug 9 - Aug 10
The Brooks Motel: Exceptional Suite
Desk, iron/ironing board, WiFi, bed sheets

2. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥25,038
￥31,592 total
includes taxes & fees
Aug 9 - Aug 10
The Brooks Motel: Exceptional Suite
Exterior

3. 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 ￥47,066
￥87,501 total
includes taxes & fees
Aug 9 - Aug 10
Gorgeous Mountain Views Retreat: Family & Nature
Exterior

4. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is ￥21,153
￥23,692 total
includes taxes & fees
Aug 9 - Aug 10
Micosta Leisure Inn
House (4 Bedrooms) | Interior

5. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is ￥37,874
￥117,325 total
includes taxes & fees
Aug 9 - Aug 10
Mtn-view Retreat in Huson Valley: Great for Groups
Lobby

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,050 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ￥16,940
￥22,462 total
includes taxes & fees
Aug 30 - Aug 31
Berkshire Mountain Lodge
TV, fireplace, printers

7. 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 ￥89,710
￥210,485 total
includes taxes & fees
Aug 13 - Aug 14
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

8. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is ￥15,546
￥20,959 total
includes taxes & fees
Aug 9 - Aug 10
All comforts of home
Interior

9. 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 ￥35,798
￥54,854 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Riverside Berkshires Retreat
Property grounds

10. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,830
￥22,400 total
includes taxes & fees
Aug 16 - Aug 17
All the comforts of home
3 bedrooms, iron/ironing board, WiFi, bed sheets

11. 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 ￥69,251
￥112,756 total
includes taxes & fees
Sep 1 - Sep 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

12. 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 ￥42,787
￥64,786 total
includes taxes & fees
Aug 12 - Aug 13
Home in Great Barrington
Property grounds

13. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥39,618
￥64,073 total
includes taxes & fees
Aug 9 - Aug 10
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Coffee/tea maker, fridge, microwave, stovetop

14. Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is ￥97,934
￥181,614 total
includes taxes & fees
Aug 9 - Aug 10
Berkshire House Stay: 5BR/5BA
Interior

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

Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (2 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 ￥32,645
￥46,731 total
includes taxes & fees
Sep 7 - Sep 8
Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake
Interior

16. 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 ￥27,732
￥50,449 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

17. Beautiful Yacht on Catskill Creek

Beautiful Yacht on Catskill Creek
Catskill
10.0 out of 10, Exceptional, (22 reviews)
"So much fun for me and my boys to stay. AJ and Melissa are great hosts!"
United States
Amy G.
The price is ￥24,959
￥52,092 total
includes taxes & fees
Aug 9 - Aug 10
Beautiful Yacht on Catskill Creek
Exterior

18. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (266 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is ￥25,399
￥34,245 total
includes taxes & fees
Sep 8 - Sep 9
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
House (3 Bedrooms) | Interior

19. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥35,497
￥87,817 total
includes taxes & fees
Aug 9 - Aug 10
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Coffee/tea maker, fridge, microwave, oven

20. 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 ￥11,410
￥33,279 total
includes taxes & fees
Aug 10 - Aug 11
NEW RENO - Chalet-style farm loft near Tanglewood
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 4 hours ago
The Red Lion Inn

Find out more about Hillsdale

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

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

Frequently asked questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

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

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Hillsdale?

With 49 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.