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Check prices for these dates

Tonight
6 Jan - 7 Jan
Tomorrow
7 Jan - 8 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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Our top choices for Hillsdale hotels

Egyptian cotton sheets, premium bedding, memory-foam beds, desk
The Brooks Motel

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (124)
"So peaceful and beautiful. Very clean ! "
United States
Asanda
The Brooks Motel
Balcony
Chatham Travel Lodge

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (214)
"Room is clean but bed uncomfortable"
United States
Vivian
The price is NZ$225
includes taxes & fees
7 Jan - 8 Jan
Chatham Travel Lodge
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is NZ$806
includes taxes & fees
20 Jan - 21 Jan
Inn at Kenmore Hall
In-room safe, blackout curtains, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.2 out of 10, Very good, (14)
"lovely place!"
United States
Samyuktha
The price is NZ$405
includes taxes & fees
27 Jan - 28 Jan
Pocketbook Hotel and Bath
John Harney Suite
The White Hart

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (145)
"Amazing stay. Incredible staff, attention to detail. Beyond expectations "
United States
Jeanette
The price is NZ$468
includes taxes & fees
12 Jan - 13 Jan
The White Hart
Front of property
it's a good thing

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
8.2 out of 10, Very good, (25)
"Lynn was a wonderful & accommodating host. Tje"
United States
Julie-Anne
it's a good thing
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is NZ$798
includes taxes & fees
20 Jan - 21 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Restaurant
Little Cat Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat Lodge
Indoor pool
Comfort Inn Saugerties

Comfort Inn Saugerties

Comfort Inn Saugerties
2.5 star property
Saugerties
7.2 out of 10, Good, (715)
"This hotel is accommodating homeless people in the cold weather. ( I appreciate the need). I would have liked to know that before… my stay was diminished because I felt like I was staying at a homeless shelter and not a hotel that I paid $$ for. We won’t stay there again. "
United States
Janet
The price is NZ$277
includes taxes & fees
12 Jan - 13 Jan
Comfort Inn Saugerties
In-room dining
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (653)
"The room was clean and the service adequate"
United States
David
The price is NZ$144
includes taxes & fees
20 Jan - 21 Jan
Econo Lodge Lee - Great Barrington
Indoor pool
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1002)
"Easy check in, friendly staff. "
United States
Daniel
The price is NZ$211
includes taxes & fees
7 Jan - 8 Jan
Howard Johnson by Wyndham Saugerties
View from room
Diamond Mills Resort

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
Saugerties
9.4 out of 10, Exceptional, (349)
"Amazing view from the room. We had a great stay. "
United States
Adam
The price is NZ$410
includes taxes & fees
7 Jan - 8 Jan
Diamond Mills Resort
Exterior
Overlook Hotel

Overlook Hotel

Overlook Hotel
2.0 star property
Saugerties
8.6 out of 10, Excellent, (26)
"Owners were super friendly and location was great! "
United States
Elliott
The price is NZ$384
includes taxes & fees
13 Jan - 14 Jan
Overlook Hotel
Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is NZ$484
includes taxes & fees
8 Jan - 9 Jan
The Inn at Stockbridge
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (461)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is NZ$131
includes taxes & fees
7 Jan - 8 Jan
Berkshire Travel Lodge
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (194)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is NZ$252
includes taxes & fees
7 Jan - 8 Jan
the Alander
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is NZ$250
includes taxes & fees
7 Jan - 8 Jan
Inn at Silver Maple Farm
The Garden Suite
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is NZ$981
includes taxes & fees
7 Jan - 8 Jan
9 Academy
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1007)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is NZ$189
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is NZ$159
includes taxes & fees
22 Jan - 23 Jan
Berkshire Inn
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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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

3.0/5 (2 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
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Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.
See properties

Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale
Red and Green Norway Maple Trees and Wood Fence

Top Hillsdale Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 20 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap accommodation in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is NZ$152 per night from 7 Jan to 8 Jan
NZ$152
7 Jan - 8 Jan
includes taxes & fees
7.4/10 Good! (827 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?
Based on Expedia's traveller preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other options for your trip to the area are The Yankee, Trademark Collection by Wyndham and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Hillsdale.
What are some of the best holiday rentals that Hillsdale has to offer?
Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Hillsdale is located on a river, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Hillsdale.
If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?
Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.
What's the best dog-friendly place to stay in Hillsdale?
The Brooks Motel is a top dog-friendly option for your stay. Hudson valley and The Berkshires Cottage is another good option for you and your pet. See more pet-friendly hotel accommodations in Hillsdale.
What are some accommodation options with pools in Hillsdale?
The Yankee, Trademark Collection by Wyndham: Offers a seasonal outdoor pool, an indoor pool and buffet. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Berkshire Mountain Lodge are a couple of other choices that feature an on-site pool. View all hotels with pools in Hillsdale.
What's it like staying in Hillsdale?
Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 65 hotels and other accommodation options to choose from. Find out more about Hillsdale.
What should I see while I'm in Hillsdale?
The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.
What's the seasonal weather in Hillsdale?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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