Hillsdale Hotels

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Hillsdale hotels

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (69)
"Nice motel, very clean, comfortable beds, i enjoyed my stay "
The price is €143
includes taxes & fees
1 Apr - 2 Apr
The Brooks Motel

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (99)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is €175
includes taxes & fees
1 Apr - 2 Apr
Blackberry River Inn

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (119)
"Beautiful and rustic, less than 15 minutes to Butternut and Great Barrington."
The price is €263
includes taxes & fees
7 Apr - 8 Apr
Gedney Farm

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (83)
"Beautiful place to stay "
The price is €296
includes taxes & fees
30 Mar - 31 Mar
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (375)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is €112
includes taxes & fees
29 Mar - 30 Mar
Locust Tree Bed and Breakfast LLC

Pilgrim Inn

2.5 star property
5.8 out of 10, (304)
"Very comfortable and in a convenient location"
The price is €72
includes taxes & fees
1 Apr - 2 Apr
Pilgrim Inn

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1057)
"Rooms wer clean and staff accomodating"
The price is €87
includes taxes & fees
13 Apr - 14 Apr
Quality Inn

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is €85
includes taxes & fees
30 Mar - 31 Mar
Sunset Inn

FairBridge Inn Express

2.5 star property
5.4 out of 10, (710)
"Friendly staff and quick checkin "
The price is €71
includes taxes & fees
29 Mar - 30 Mar
FairBridge Inn Express

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is €248
includes taxes & fees
4 Apr - 5 Apr
Chambery Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is €67
includes taxes & fees
30 Mar - 31 Mar
Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is €258
includes taxes & fees
30 Mar - 31 Mar
Devonfield Inn B&B

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1096)
"Beautiful views of the lake with cozy rooms. Staff is excellent. "
The price is €96
includes taxes & fees
3 Apr - 4 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection

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

3.5 star property
9.0 out of 10, Wonderful, (612)
"I loved it so much to do"
The price is €136
includes taxes & fees
31 Mar - 1 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (629)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is €155
includes taxes & fees
30 Mar - 31 Mar
Hilton Garden Inn Lenox Pittsfield

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is €61
includes taxes & fees
29 Mar - 30 Mar
Wagon Wheel Inn

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (716)
"No issues"
The price is €71
includes taxes & fees
29 Mar - 30 Mar
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (443)
"We had a great time at the hotel. My sons and I loved spending time in the pool and the hot tub. The bedroom was spacious, the kitchen had everything we needed, and the bathroom was ample and clean."
The price is €154
includes taxes & fees
30 Mar - 31 Mar
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1047)
"Some bathroom fixtures are old and rust stained. A light refresh of some inexpensive items would go a long way to make the place look well maintained. The staff was excellent. Friendly and professional. The breakfast area was clearly well maintained a it was spotless. "
The price is €131
includes taxes & fees
8 Apr - 9 Apr
Hampton Inn & Suites Berkshires-Lenox

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (696)
"Nice stay at the property, the rooms are huge… the wooden floors do creek a bit so you can hear people walking around but if you don’t mind that, it’s a pretty cool hotel, nicely decorated. "
The price is €113
includes taxes & fees
1 Apr - 2 Apr
Hotel On North
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.
Don't see what you're looking for?
See all available properties in Hillsdale
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Hillsdale

Quaint Hillsdale is calling! Discover its coffee, library, horse riding and more.

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 19.2 mi (31 km) from the heart of Hillsdale, Life House Berkshires is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Hillsdale is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. 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 hotel for families in Hillsdale?

Holiday House Motel is a property with free parking and free WiFi, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Catamount Aerial Adventure Park.

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's the best hotel for a trip to the slopes in Hillsdale?

Little Cat Lodge is a top hotel for a winter getaway, and features ski storage and free WiFiThis hotel is adjacent to Catamount Ski Area. The Brooks Motel is another good choice for your winter getaway. See all ski hotels 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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and Howard Johnson by Wyndham Saugerties 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 70 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.