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Our top choices for Hillsdale hotels

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (892 reviews)
"Great place to stay. Nice bar with outdoor fireplace."
United States
Joseph
4 days ago
$103 nightly
The price is $115
Apr 12 - Apr 13
Total with taxes and fees
Berkshires Untold

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (897 reviews)
"Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight."
United States
Leslieann H
8 days ago
$108 nightly
The price is $120
May 10 - May 11
Total with taxes and fees
Berkshire Mountain Lodge

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
3.5 star property
South Lee
9.0 out of 10, Wonderful, (861 reviews)
"Incredible for incredibly difficult time for our family. This has been absolutely amazing."
United States
Chris
8 days ago
$130 nightly
The price is $145
Apr 13 - Apr 14
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (23 reviews)
"We had an incredible time relaxing by using all the amenities."
United States
Kate
November 29th, 2025
$285 nightly
The price is $319
Apr 20 - Apr 21
Total with taxes and fees
Prospect Berkshires

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, (999 reviews)
"Rooms were clean. Our room had 2 queen beds. There are several breakfast."
United States
SANDEEP
February 2nd, 2026
$118 nightly
The price is $132
May 10 - May 11
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (133 reviews)
"Will definitely consider staying there again. The room is clean."
United States
Michael
January 29th, 2026
$112 nightly
The price is $126
Apr 13 - Apr 14
Total with taxes and fees
The Brooks Motel

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (75 reviews)
"Rooms are warm. Beds are soft."
United States
Alexandra
10 days ago
$189 nightly
The price is $212
Apr 12 - Apr 13
Total with taxes and fees
Little Cat Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Room temperature was good. Breakfast coukd improve."
United States
Kathy
7 days ago
$99 nightly
The price is $111
Apr 19 - Apr 20
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (754 reviews)
"Nice warm pool and hot tub. Good little fitness center."
United States
Fawn
January 2nd, 2026
$107 nightly
The price is $120
Apr 20 - Apr 21
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Room was comfortable. Staff accommodated a request to change rooms."
United States
Nathaniel
13 days ago
The Yankee, Trademark Collection by Wyndham

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (776 reviews)
"Staff was lovely, everything was easy, clean and comfortable."
United States
Helena
March 8th, 2026
$152 nightly
The price is $170
Apr 14 - Apr 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,000 reviews)
"The Quality Inn in Great Barrington is a good value play."
United States
Leslie
9 days ago
$67 nightly
The price is $75
Apr 26 - Apr 27
Total with taxes and fees
Quality Inn Great Barrington

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (214 reviews)
"Delightful and well appointed stay! Close to so many things and very cozy."
United States
Jackie
10 days ago
$140 nightly
The price is $157
Apr 12 - Apr 13
Total with taxes and fees
the Alander

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck Village
8.4 out of 10, Very Good, (860 reviews)
"The room was very nice clean and fresh."
United States
Noel
December 27th, 2025
$159 nightly
The price is $180
Apr 13 - Apr 14
Total with taxes and fees
Beekman Arms and Delamater Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (838 reviews)
"Very clean and cozy in a great location!"
United States
Lidia
4 days ago
$67 nightly
The price is $74
Apr 12 - Apr 13
Total with taxes and fees
Monument Mountain Motel

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"Can't wait to go back again. Feels like going back in time."
United States
Susan
6 days ago
$189 nightly
The price is $211
Apr 12 - Apr 13
Total with taxes and fees
The Red Lion Inn

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
Saugerties
9.4 out of 10, Exceptional, (367 reviews)
"Great for a quick getaway. Nice sized rooms, heated bathroom floors. Overall great experience."
United States
Stephen
3 days ago
$294 nightly
The price is $326
Apr 13 - Apr 14
Total with taxes and fees
Diamond Mills Resort

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (98 reviews)
"Beautiful home with warm. The rooms were tastefully designed."
United States
Nicole
2 days ago
$174 nightly
The price is $194
Apr 12 - Apr 13
Total with taxes and fees
Granville House

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington."
United States
Laura
5 days ago
$120 nightly
The price is $134
Apr 28 - Apr 29
Total with taxes and fees
East Rock Inn

Mirbeau Inn & Spa

Mirbeau Inn & Spa
4.0 star property
Rhinebeck Village
9.6 out of 10, Exceptional, (316 reviews)
"The spa is always top notch. The rooms are always clean."
United States
christian
January 4th, 2026
$428 nightly
The price is $484
Apr 12 - Apr 13
Total with taxes and fees
Mirbeau Inn & Spa
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Stay near popular Hillsdale attractions

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.

Red and Green Norway Maple Trees and Wood Fence

Top Hillsdale Hotel Reviews

More cheap stays in Hillsdale

Hotels in Hillsdale with star-rating

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Outdoor Adventure: Hillsdale is perfect for skiing, hiking, and exploring beautiful national parks and lakes.
  • Thrilling Activities: Experience zip line adventures for an adrenaline rush amidst stunning scenery.
  • Serene Wellness Retreats: Enjoy relaxation and rejuvenation at local wellness retreats surrounded by nature.
  • Charming Accommodations: Stay at cozy bed & breakfasts and agritourism properties with warm hospitality.
  • Family-Friendly Atmosphere: Hillsdale offers picnic spots and activities ideal for families and couples.

Find great hotels near Hillsdale

Discover the charming accommodations in Hillsdale, New York, where a blend of agritourism properties and cozy bed & breakfasts await. Perfect for families and adventure seekers, you'll find pet-friendly options and warm hospitality at places like the Hillsdale House Inn and Brooks Motel. Whether you're seeking a relaxing retreat or an active getaway, Hillsdale offers a variety of lodging to make your stay memorable.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the scenic Berkshires, about 14 miles from Hillsdale, this 3.5-star resort boasts a remarkable guest rating of 9.0. It’s perfect for families seeking a memorable vacation experience, complete with ski access and a variety of child-friendly amenities. Guests can enjoy an on-site mini-golf course, arcade game room, and a playground designed for children. The resort's cozy accommodations and inviting atmosphere make it an ideal choice for those looking to unwind after a day of skiing or exploring the beautiful surroundings.
  • Quality Inn Great Barrington: A budget-friendly option located just 8 miles from Hillsdale, the Quality Inn Great Barrington offers an excellent guest rating of 8.4. This hotel is a great fit for adventurous travelers and business guests alike, providing easy access to outdoor activities such as hiking, biking, and various winter sports. With ski rentals and lessons available nearby, you can easily dive into the region's outdoor offerings. The friendly staff and comfortable accommodations ensure a pleasant stay for all guests.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 9 miles from Hillsdale, this budget-friendly hotel has a solid guest rating of 8.8. Ideal for business travelers, the Holiday Inn Express Hotel & Suites combines convenience with comfort. Guests will appreciate the modern amenities and complimentary breakfast that kick-starts your day. This hotel’s strategic location enables easy access to nearby business districts and local attractions, making it a smart choice for those on the go.

Where to stay near Hillsdale

Hillsdale, New York, offers a perfect blend of outdoor adventure and serene relaxation. Visitors can enjoy skiing and exploring the scenic views of the surrounding areas. Nearby attractions provide a friendly atmosphere ideal for families and couples alike, with plenty of picnic spots to unwind. Don't miss the charming Hillsdale College, which adds to the area's character. Whether you're seeking adventure or a peaceful getaway, Hillsdale has something for everyone.

  • Great Barrington: Situated 8 miles from Hillsdale, Great Barrington is a vibrant city that attracts visitors year-round. However, the peak travel season falls between June and August. Known for its exceptional outdoor activities, Great Barrington is a haven for adventure seekers, particularly those interested in skiing and sports. The area boasts stunning landscapes, with nearby lakes and mountains, making it perfect for both relaxation and recreation. Don’t miss the chance to explore the local ski resorts and take in the natural beauty of the surrounding national state park.
  • Craryville: Located just 3 miles from Hillsdale, Craryville is a charming city that offers a moderately seasonal travel experience, with visitor numbers peaking throughout the year. Outdoor enthusiasts flock here for its adventure and skiing opportunities. The ski fields and resorts are popular attractions, drawing in those eager for winter sports. Craryville is surrounded by picturesque lakes and mountains, providing plenty of options for hiking and exploring the great outdoors. Its proximity to national state parks ensures visitors can soak in the beauty of nature while enjoying various recreational activities.
  • Copake: About 5 miles from Hillsdale, Copake is a delightful city that experiences a diverse flow of visitors throughout the year, with peak travel times in March to April and July. It is known for its outdoor and adventure experiences, particularly skiing. With ski resorts and fields at your fingertips, Copake is ideal for those looking to hit the slopes. The area is also home to beautiful lakes and mountains, making it a great spot for hiking and sightseeing. Explore the nearby national state park to truly appreciate the natural wonders that Copake has to offer.

Things to do in Hillsdale

Hillsdale, New York, is an ideal destination for outdoor enthusiasts, offering a range of activities such as skiing at local resorts and exploring scenic ski fields. Visitors can also enjoy wellness retreats for relaxation and rejuvenation, as well as thrilling zip line adventures for an adrenaline rush. Whether you're hitting the slopes or seeking relaxation, Hillsdale provides a perfect blend of adventure and tranquility.

Shopping

In Hillsdale, you can find charming local shops offering unique gifts and souvenirs. If you're up for a drive, visit the Great Barrington Plaza, about 12 miles away, for a variety of retail stores and boutiques. The Hudson Valley Antique Center is also worth the trip for vintage finds.

Recreation

Explore the tranquil setting of the Hillsdale Wellness Center, where you can enjoy yoga classes and holistic therapies. For outdoor fun, visit nearby Bash Bish Falls State Park for hiking, offering scenic views and a refreshing escape into nature.

Adventure

In Hillsdale, explore the scenic trails of the Catamount Ski Area for hiking and mountain biking, offering breathtaking views. Experience exhilarating zip-lining adventures at the nearby Catamount Adventure Park, perfect for thrill-seekers looking to soar through the treetops amidst stunning landscapes.

Nightlife

The nightlife in Hillsdale offers cozy spots like The Hillsdale Tavern for a laid-back vibe. For something more lively, check out nearby bars featuring live music and dancing. Enjoy a relaxed evening with friends, savoring local brews and the friendly atmosphere that Hillsdale has to offer.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Hillsdale

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Hillsdale are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Hillsdale is Tuesday. The most expensive day to stay in Hillsdale is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool makes it easy to choose your budget, preferred location, and additional preferences. You can arrange your search results to display hotels from the lowest to the highest price, ensuring you find the most affordable options first. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Hillsdale with your flights and activities by choosing an Expedia package.

Find the best attractions near Hillsdale

Hillsdale, New York, is perfect for outdoor enthusiasts seeking adventure and culture. Visitors can enjoy skiing and various outdoor activities in stunning natural settings, including national parks, nature reserves, and beautiful lakes. Whether you're looking for thrilling adventures or a peaceful retreat, Hillsdale offers a variety of attractions that cater to all types of travelers eager to explore the great outdoors.

  • National Shrine of the Divine Mercy: Experience a serene atmosphere at this spiritual haven located 13 miles from Hillsdale. The shrine features beautiful architecture and tranquil gardens, inviting visitors to reflect and meditate amidst its cultural significance.
  • Norman Rockwell Museum: Situated 12 miles away, this museum showcases the iconic works of artist Norman Rockwell. Explore his timeless illustrations that capture the essence of American life, complemented by engaging exhibits that provide insight into his creative process.
  • Taconic State Park: Just 4 miles from Hillsdale, this stunning park offers breathtaking scenery and outdoor adventures. Enjoy hiking, picnicking, or simply soaking in the natural beauty of the Hudson Valley, making it ideal for nature lovers and thrill-seekers alike.

Best time to go to Hillsdale

The best time to visit Hillsdale can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Hillsdale falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Hillsdale falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighSlightly Low
February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighAverage
March34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July72.0°F (22.2°C)Light RainMostly SunnySlightly HighSlightly High
August70.0°F (21.1°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnySlightly LowSlightly High
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Hillsdale

When planning your trip to Hillsdale, New York, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is 46 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport. ALBany International Airport (ALB) is 42 miles from Hillsdale, featuring hotels such as The Landing Hotel at Rivers Casino & Resort, located 8 miles from the airport. For those considering White Plains, NY (HPN), located 77 miles away, hotels like The Opus Westchester offer convenient airport shuttle services. Each airport provides various accommodation options to ensure a comfortable stay during your visit.

Frequently asked questions

What is the best area to stay in Hillsdale?
The best area to stay in Hillsdale is in the village center, particularly around the intersection of Route 22 and Route 23.

This area is the heart of Hillsdale, offering easy access to local establishments and a pleasant, walkable environment. You'll find a few charming shops, cafes, and restaurants concentrated along these main roads. It provides a convenient base to explore the surrounding natural beauty and nearby towns.

Couples looking for a peaceful getaway will appreciate the village center's relaxed pace and access to local dining. It's an ideal spot for those who enjoy strolling through a small town and finding unique local treasures.

For travelers interested in outdoor activities, staying near the village center puts you within a short drive of hiking trails, nature preserves, and scenic drives.
What are the best hotels in Hillsdale that travelers recommend?
For travelers looking for a highly recommended hotel in Hillsdale, The Brooks Motel is an excellent option.

The Brooks Motel has a 7.6 rating and is praised by guests for its super comfy and clean beds, modern and clean rooms, and excellent customer service. This motel offers premium bedding, air conditioning, and fireplaces in the rooms. For those interested in winter sports, it's conveniently located near a ski area, with opportunities for cross-country skiing, downhill skiing, and access to ski lifts and runs. Additionally, it is just 1.2 miles from Catamount Aerial Adventure Park.
What are the top pet-friendly hotels in Hillsdale?
For pet-friendly hotels in Hillsdale, consider The Brooks Motel.

The Brooks Motel has a 7.6 rating and is a convenient option for travelers with dogs, as it offers a Dogs Only policy and allows pets to stay free. Guests frequently mention the super comfy and clean beds, as well as the modern and clean rooms. The customer service also receives excellent remarks. Additionally, it is located just 1.2 miles from Catamount Aerial Adventure Park and is convenient for those interested in various skiing activities, including downhill, cross-country, and ski lifts. See more pet-friendly hotels in Hillsdale
What are the best budget hotels in Hillsdale?
For a budget-friendly stay in Hillsdale, The Brooks Motel is an excellent option that travelers frequently recommend.

This motel has a 7.6 rating and is often praised for its super comfy and clean beds, as well as its modern and clean rooms. Guests consistently highlight the excellent customer service. Key amenities include free WiFi and complimentary self-parking. For those interested in winter sports, the motel is conveniently located near various ski areas, including cross-country, downhill, and ski lifts. View all budget hotels in Hillsdale
What are the best hotels in Hillsdale near Catamount Aerial Adventure Park?
For a great hotel in Hillsdale near Catamount Aerial Adventure Park, consider The Brooks Motel.

The Brooks Motel has a 7.6 rating and is conveniently located just 1.2 miles from Catamount Aerial Adventure Park. Guests often highlight the super comfy and clean beds, the modern and clean rooms, and the excellent customer service. This hotel offers free WiFi, free self-parking, and allows pets to stay free. It is also well-suited for those interested in skiing, with nearby access to ski areas, cross-country, downhill, ski lifts, and ski runs.
When is the best time to go to Hillsdale?
For most visitors, the best time to go to Hillsdale is during the summer months, from June to August, when the weather is ideal for outdoor activities, or in the fall, from September to October, for the foliage.

Summer in Hillsdale offers warm, sunny days, great for exploring the local hiking trails, swimming in nearby lakes, or visiting farmers' markets. The area thrives with outdoor events and opportunities to enjoy the natural beauty of the Berkshire foothills. Couples will find this period ideal for scenic drives, winery visits, and dining al fresco.

The fall season transforms Hillsdale into a picturesque landscape of vibrant colors, making it an excellent time for those who appreciate natural scenery and photography. The cooler temperatures are comfortable for exploring antique shops and art galleries, and many local farms offer apple picking and pumpkin patches.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Hillsdale.
How can I save on a Hillsdale hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Hillsdale hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Hillsdale hotel?
Prices for hotels in Hillsdale often vary, but you can find a great deal from $75 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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