Hillsdale hotels from HK$686

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28 Dec - 29 Dec
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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, (120)
Stay at this inviting Hillsdale motel near Catamount Aerial Adventure Park. Enjoy premium bedding after a day of skiing and snowboarding in the area. Convenient amenities include free WiFi and parking.
"Unbearably hard bed, very small room, particle board decor, icy cold cement floor. We checked out within minutes of arriving. "
United States
Carmen
The Brooks Motel
Terrace/patio
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)
Escape to this elegant retreat offering free continental breakfast and WiFi near Clinton Vineyards. Rooms feature refrigerators and microwaves, while outdoor spaces include a garden and terrace. Stanford Recreation Park and Rhinecliff Station are conveniently accessible.
"Lynn was a wonderful & accommodating host. Tje"
United States
Julie-Anne
it's a good thing
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
Relax at this inviting lodge near Catamount Ski Area featuring a seasonal outdoor pool and restaurant. After adventures, unwind in the sauna or garden, or sip drinks at the bar while enjoying free breakfast, WiFi, and parking.
"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
Exterior
Chatham Travel Lodge

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (214)
Peaceful countryside motel offers daily housekeeping, free WiFi, and complimentary parking. Explore nearby attractions like The Mac-Haydn Theatre or Shaker Museum, with convenient access to Hudson Station and airport.
"Room is clean but bed uncomfortable"
United States
Vivian
The price is HK$901
HK$1,010 total
includes taxes & fees
30 Dec - 31 Dec
Chatham Travel Lodge
Desk, iron/ironing board, free cots/infant beds, rollaway beds
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, (652)
Set in Lee, this motel offers fun mini golf on the property and free continental breakfast each morning. Just a short drive from Greenock Country Club and shopping at Lee Premium Outlets, guests appreciate the attentive staff and convenient free parking.
"The room was clean and the service adequate"
United States
David
The price is HK$581
HK$649 total
includes taxes & fees
11 Jan - 12 Jan 2026
Econo Lodge Lee - Great Barrington
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 HK$3,303
HK$3,623 total
includes taxes & fees
5 Jan - 6 Jan 2026
Inn at Kenmore Hall
Lobby
Pilgrim Inn

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332)
Experience countryside tranquility at this golf-adjacent hotel in Lee, where free WiFi and parking enhance your stay. Explore nearby Lee Library and Animagic Museum, or embrace seasonal activities like cross-country skiing and snowboarding.
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is HK$622
HK$695 total
includes taxes & fees
1 Jan - 2 Jan 2026
Pilgrim Inn
Business centre
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)
Luxurious B&B featuring a seasonal outdoor pool and beautiful terrace surrounded by nature. Enjoy complimentary breakfast before hiking nearby trails or kayaking. Just minutes from Tanglewood Music Centre with free WiFi and parking for seamless exploration.
"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 HK$2,968
HK$3,590 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Restaurant
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)
Surprisingly peaceful despite highway proximity, this hotel offers relaxing amenities including a sauna and garden. The helpful staff, convenient location near Kiwanis Ice Arena, plus in-room refrigerators make for a comfortable stay.
"Easy check in, friendly staff. "
United States
Daniel
The price is HK$956
HK$1,071 total
includes taxes & fees
25 Jan - 26 Jan 2026
Howard Johnson by Wyndham Saugerties
Iron/ironing board, free cots/infant beds, free rollaway beds, free WiFi
Comfort Inn Saugerties

Comfort Inn Saugerties

Comfort Inn Saugerties
2.5 star property
Saugerties
7.2 out of 10, Good, (714)
Conveniently situated in Saugerties, this welcoming hotel offers free breakfast and WiFi. The indoor pool provides year-round relaxation, while Kiwanis Ice Arena and HITS-on-the-Hudson are just minutes away.
"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 HK$989
HK$1,107 total
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn Saugerties
Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (144)
Set in Salisbury near Mount Frissell, this historic hotel welcomes you with free breakfast and WiFi. After exploring nearby Hanging Rock Park, relax in the garden or enjoy a drink at the bar while savouring the terrace views.
"Great charming place, friendly, helpful staff"
United States
David
The price is HK$2,195
HK$2,524 total
includes taxes & fees
4 Jan - 5 Jan 2026
The White Hart
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
8.0 out of 10, Very good, (11)
Experience modern comfort in Hudson's historic district, complete with a relaxing full-service spa and convenient cafe. Just minutes from Hudson Area Library and within walking distance of local attractions, this refined retreat offers complimentary WiFi.
"lovely place!"
United States
Samyuktha
The price is HK$1,516
HK$2,065 total
includes taxes & fees
19 Jan - 20 Jan 2026
Pocketbook Hotel and Bath
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374)
Experience tranquility at this peaceful B&B in Lee, where deep-tissue massages and aromatherapy await. Just a 10-minute drive from Tanglewood Music Centre, guests enjoy access to a hot tub, terrace, and snack bar while exploring nearby Berkshire attractions.
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Centre, with hiking trails waiting for exploration.
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is HK$699
HK$781 total
includes taxes & fees
30 Dec - 31 Dec
Sunset Inn
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is HK$1,249
HK$1,465 total
includes taxes & fees
30 Dec - 31 Dec
Lakehouse Inn
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (91)
Discover this charming B&B in Housatonic offering complimentary full breakfast, WiFi, and parking. Conveniently located near Monument Mountain and its reservation, this business-friendly getaway provides a perfect base for exploring local attractions.
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is HK$1,546
HK$1,727 total
includes taxes & fees
1 Jan - 2 Jan 2026
Granville House
Premium bedding, pillow-top beds, minibar, in-room safe
Diamond Mills Resort

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
Saugerties
9.4 out of 10, Exceptional, (347)
"Amazing view from the room. We had a great stay. "
United States
Adam
The price is HK$1,420
HK$1,785 total
includes taxes & fees
4 Jan - 5 Jan 2026
Diamond Mills Resort
American cuisine
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (191)
Discover tranquility at this countryside lodge featuring the North Star restaurant serving American cuisine for dinner. Enjoy free WiFi and parking while exploring nearby Undermountain Golf Course and Copake Town Park. Rooms offer rainfall showerheads for extra comfort.
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is HK$1,088
HK$1,219 total
includes taxes & fees
5 Jan - 6 Jan 2026
the Alander
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
This charming 4-star retreat offers complimentary self-parking and WiFi in a serene setting. Explore nearby Mount Frissell and Scoville Memorial Library, or enjoy seasonal outdoor adventures like snowboarding and canoeing.
"Nice room. "
South Korea
JeongHoon
The price is HK$3,837
HK$4,413 total
includes taxes & fees
5 Jan - 6 Jan 2026
9 Academy
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
Devonfield Inn B&B offers massages, free breakfast, and complimentary WiFi near Greenock Country Club. The charming property features a lovely terrace and garden, with free parking for easy exploration of nearby attractions.
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
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.
See properties

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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Clean room, friendly staff"
Dawn 1-night trip
Posted 2 days ago
Courtyard by Marriott Lenox Berkshires

More cheap stays in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is HK$614 per night from 30 Dec to 31 Dec
HK$614
HK$686 total
30 Dec - 31 Dec
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 64 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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