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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Hillsdale holiday homes

Dining

Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful home in a very quiet and peaceful neighborhood. Well stocked kitchen, bathrooms etc. immaculately clean! "
United States
denise g.
The price is HK$1,212
HK$4,685 total
includes taxes & fees
25 Feb - 26 Feb
Super Comfortable Water-view Home in Saugerties
Outdoor dining

Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties
Saugerties
9.6 out of 10, Exceptional, (11 reviews)
"The home was amazing! Do recommend."
United States
Cole B.
The price is HK$2,325
HK$4,967 total
includes taxes & fees
25 Feb - 26 Feb
Charming 2-bedroom Waterfront home with boat access in Saugerties
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (39 reviews)
"Cute house in a great location. Thanks for the stay!"
United States
Nicole S.
The price is HK$1,329
HK$3,178 total
includes taxes & fees
3 Mar - 4 Mar
Brand New House w gated backyard that is located right at the Saugerties Village
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is HK$830
HK$1,105 total
includes taxes & fees
2 Mar - 3 Mar
All the comforts of home
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,400
HK$2,385 total
includes taxes & fees
25 Feb - 26 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (8 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is HK$1,250
HK$2,667 total
includes taxes & fees
26 Feb - 27 Feb
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,582
HK$2,475 total
includes taxes & fees
26 Feb - 27 Feb
Family Ski Getaway in the Berkshires
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$844
HK$2,634 total
includes taxes & fees
25 Feb - 26 Feb
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,259
HK$2,105 total
includes taxes & fees
25 Feb - 26 Feb
Home in Great Barrington
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,337
HK$5,080 total
includes taxes & fees
25 Feb - 26 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor pool, a heated pool

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (30 reviews)
"The home was as described. Exceptional. It was immaculate and well stocked."
United States
judy h.
The price is HK$4,728
HK$8,513 total
includes taxes & fees
4 Mar - 5 Mar
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,261
HK$4,014 total
includes taxes & fees
25 Feb - 26 Feb
Artists’ Hideaway in Old Chatham
Terrace/patio

Vintage charm with modern conveniences on the water in Saugerties, NY!

Vintage charm with modern conveniences on the water in Saugerties, NY!
Saugerties
9.4 out of 10, Exceptional, (6 reviews)
"We had a great time at your house . The view was so relaxing and lovely. The kitchen was fully functional and the neighbors were very quiet. Thanks "
United States
keren m.
The price is HK$1,641
HK$3,308 total
includes taxes & fees
11 Mar - 12 Mar
Vintage charm with modern conveniences on the water in Saugerties, NY!
Outdoor dining

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
7.8 out of 10, Good, (7 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$2,103
HK$3,868 total
includes taxes & fees
25 Feb - 26 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is HK$964
HK$2,752 total
includes taxes & fees
8 Mar - 9 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries
TV, fireplace, printers

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, (3 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$4,424
HK$10,380 total
includes taxes & fees
26 Feb - 27 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, offices

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
8.8 out of 10, Excellent, (3 reviews)
"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "
United States
raquel p.
The price is HK$1,019
HK$3,248 total
includes taxes & fees
25 Feb - 26 Feb
Catskill Stay w/ Deck & Fire Pit
TV, video games

New! The Den on Denniston, with game room, movie theater, fire pit and more. Close To HITS Horse show & Hunter Mountain skiing

New! The Den on Denniston, with game room, movie theater, fire pit and more. Close To HITS Horse show & Hunter Mountain skiing
Saugerties
10.0 out of 10, Exceptional, (1 review)
"My wife and I spent an evening in this wonderful space and we couldn't have been more pleased! 10/10 would recommend."
United States
Lionel J.
The price is HK$1,309
HK$3,776 total
includes taxes & fees
2 Mar - 3 Mar
New! The Den on Denniston, with game room, movie theater, fire pit and more. Close To HITS Horse show & Hunter Mountain skiing
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is HK$1,094
HK$2,147 total
includes taxes & fees
25 Feb - 26 Feb
Hudson Hot Tub & Pet Escape
Fridge, microwave, oven, stovetop

Modern getaway in Catskills

Modern getaway in Catskills
Cairo
10.0 out of 10, Exceptional, (13 reviews)
"The host was accommodating and the house was very nice!"
United States
Ken B.
The price is HK$3,860
HK$6,576 total
includes taxes & fees
5 Mar - 6 Mar
Modern getaway in Catskills
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Room was spotless! Kitchen was so helpful. Pool was a major hit with the kids and was warm even though it was February! They spent hours in the pool and outdoor hot tub. Will definitely stay here again!"
April 1-night trip
Posted 12 hours ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
218
Accommodation
641 Vacation Homes
Lowest Price
HK$1,105
Highest Price
HK$10,380

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