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Our top choices for Hillsdale hotels

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (138 reviews)
"Nice "
United States
Daljit
The price is AU$202
includes taxes & fees
17 June - 18 June
The Brooks Motel

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is AU$203
includes taxes & fees
9 June - 10 June
Berkshire Lake Lodge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
"beautiful inn"
United States
Maura
The price is AU$245
includes taxes & fees
21 June - 22 June
Blackberry River Inn

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
"Had a great stay. Beautiful location."
United States
Joan
The price is AU$283
includes taxes & fees
21 June - 22 June
Gedney Farm

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is AU$565
includes taxes & fees
9 June - 10 June
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (418 reviews)
"Below average B&B"
United States
Larry
The price is AU$171
includes taxes & fees
12 June - 13 June
Locust Tree Bed and Breakfast LLC

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332 reviews)
"Wonderful fantastic "
United States
Bryron
The price is AU$284
includes taxes & fees
2 July - 3 July
Pilgrim Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AU$194
includes taxes & fees
11 June - 12 June
Quality Inn Lee - Lenox South

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (415 reviews)
"Nice place for a stay"
United States
Jay
The price is AU$166
includes taxes & fees
9 June - 10 June
Sunset Inn

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (824 reviews)
"Quiet"
United States
William
The price is AU$109
includes taxes & fees
22 June - 23 June
FairBridge Inn Express

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (378 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AU$271
includes taxes & fees
9 June - 10 June
Chambery Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is AU$113
includes taxes & fees
14 June - 15 June
Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AU$521
includes taxes & fees
14 June - 15 June
Devonfield Inn B&B

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, (1,002 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is AU$218
includes taxes & fees
22 June - 23 June
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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
9.2 out of 10, Wonderful, (906 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is AU$240
includes taxes & fees
11 June - 12 June
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (101 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is AU$214
includes taxes & fees
14 June - 15 June
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (681 reviews)
"Five Star stay!"
United States
Adeline
The price is AU$232
includes taxes & fees
14 June - 15 June
Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (863 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AU$125
includes taxes & fees
9 June - 10 June
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (968 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is AU$233
includes taxes & fees
7 July - 8 July
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Good location and great breakfast."
United States
Linda
The price is AU$232
includes taxes & fees
14 June - 15 June
Hampton Inn & Suites Berkshires-Lenox
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

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 accommodation in Hillsdale

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Thrilling Ski Resorts: Hillsdale is a haven for ski enthusiasts, featuring excellent slopes and resorts for an adrenaline-packed adventure.
  • Picturesque Nature: Explore stunning national parks, serene lakes, and nature reserves, perfect for outdoor adventures and relaxation.
  • Cultural Entertainment: Enjoy a vibrant atmosphere filled with arcade games, live performances, and weekly cultural events.
  • Charming Towns: Wander through friendly local towns that boast beautiful scenery and inviting vibes.
  • Varied Accommodation: Choose from delightful bed and breakfasts or unique agritourism properties tailored for every traveller.

Find great hotels near Hillsdale

Discover the charm of Hillsdale, New York, with a range of delightful accommodation options tailored for every traveller. From inviting bed and breakfasts to unique agritourism properties, Hillsdale's hotels cater to families, pet owners, and adventure seekers alike. Whether you're searching for the best Hillsdale hotels or the cosy ambiance of a hillside retreat, you're sure to find the perfect spot to relax and enjoy your getaway.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 22.5km from Hillsdale, this 3.5-star resort is ideal for families and adventure seekers alike. With a vibrant atmosphere that welcomes LGBTQIA travellers, the property offers a plethora of onsite activities, including mini-golf and an arcade game room for kids. Adventure enthusiasts can explore nearby hiking trails, ski resorts, and snowboarding opportunities, ensuring an action-packed getaway. The resort’s child-friendly amenities, such as free cribs and shared playgrounds, make it a perfect choice for families wishing to create lasting memories.
  • Quality Inn: Located 12.9km from Hillsdale, Quality Inn is a practical choice for business travellers and adventure lovers. The hotel provides essential business amenities, catering to those on a work trip while still wanting to enjoy the great outdoors. Guests can take advantage of nearby skiing, snowboarding, and hiking opportunities, ensuring that there's never a dull moment. The Quality Inn strikes a balance between professional convenience and recreational pursuits, making it an excellent choice for those who want to blend work and play.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 14.5km from Hillsdale, this hotel combines business efficiency with a welcoming vibe for LGBTQIA guests. It features comprehensive business facilities, including a 24-hour business centre, meeting rooms, and conference spaces, making it suitable for corporate travellers. The modern accommodations and convenient amenities ensure a comfortable stay while allowing guests to unwind after a day of meetings. With its strategic location, this hotel is perfect for those who seek a productive visit to the area.

Where to stay near Hillsdale

Hillsdale, New York, offers an enchanting escape for adventure lovers and those seeking a relaxing vibe. Explore nearby ski resorts for thrilling slopes, or wander through charming towns that exude a friendly atmosphere and stunning scenery. Enjoy alfresco dining with a delightful evening breeze, and take in the captivating city views. Whether you’re after a romantic getaway or a family-friendly adventure, Hillsdale and its surroundings promise memorable experiences for every traveller.

  • Great Barrington: Nestled 12.9km from Hillsdale, Great Barrington is a vibrant city renowned for its outdoor adventures. Visitors flock here for skiing, sports activities, and a plethora of thrilling experiences. The peak season runs from June to August, but the area is enchanting year-round. Nature enthusiasts will appreciate the stunning landscapes featuring lakes, mountains, and the nearby national state park, making it a perfect spot for outdoor explorations and relaxation.
  • Stockbridge: Located 20.9km from Hillsdale, Stockbridge is a cultural gem famed for its romantic ambiance and artistic flair. This city draws visitors primarily from July to September, offering a delightful mix of entertainment, including music concerts and theatrical performances. The nearby lakes, historic monuments, and serene shrines provide a picturesque backdrop for leisurely strolls and cultural immersion. Stockbridge is the ideal destination for those seeking an enriching and enchanting experience.
  • Copake: Just 8.0km away from Hillsdale, Copake is a fantastic choice for adventure seekers and outdoor enthusiasts. The city sees increased visitor numbers mainly in March, April, and July, with skiing and outdoor activities at the forefront of its appeal. With its proximity to breathtaking lakes, majestic mountains, and a national state park, Copake offers countless opportunities for exploration and excitement. It’s a perfect base for those eager to embrace both adventure and the beauty of nature.

Things to do in and around Hillsdale

Hillsdale offers a fantastic getaway for adventure lovers, particularly those keen on skiing, with excellent ski resorts and fields. In addition to outdoor activities, you'll find plenty of entertainment options, including arcade games and live performances, alongside a variety of weekly events that showcase the local culture. Whether you're hitting the slopes or enjoying the vibrant atmosphere, Hillsdale has something for everyone.

Shopping

In Hillsdale, you can visit local gems like Charles H. Baldwin & Sons, Hoffman's Pottery, and Ebenezer II Gifts and Antiques, all located 20.9km away. If you're up for a drive, these stores offer unique gifts and souvenirs to take home.

Recreation

At Tanglewood Music Center, immerse yourself in enchanting music concerts that elevate your spirit, located 25.7km from Hillsdale. Experience wellness and tranquillity at Lake Mansfield Park, 12.9km away, or enjoy outdoor activities at the Undermountain Golf Course, also 12.9km from Hillsdale.

Adventure

At Catamount Aerial Adventure Park, soar through the treetops on thrilling ziplines and tackle challenging ropes courses, all while soaking up the outdoor atmosphere. Experience exhilarating skiing at Catamount Ski Area, located 3.2km away, or enjoy a scenic hike along the Housatonic River Walk, situated 14.5km from Hillsdale.

Nightlife

For a vibrant night out near Hillsdale, catch a show at the Mahaiwe Performing Arts Center, just 12.9km away, or enjoy a performance at the Mac-Haydn Theatre, 20.9km down the road. The Ancram Opera House, 17.7km away, offers a charming cultural experience.

Booking tips and Expedia advantages for Hillsdale

To save money during your trip to Hillsdale, consider visiting in January or March to April when accommodation prices are lower. Tuesdays are the most budget-friendly days for stays, while Saturdays tend to be pricier. Use Expedia to search for eco-friendly hotels and sort options by price for the best deals. Additionally, package your hotel with flights and activities for extra savings. Enjoy free outdoor activities like hiking and explore local parks to make the most of your budget while experiencing the beauty of 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of accommodation you’re after. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some cash by combining your Hillsdale hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Hillsdale

Hillsdale, New York, is perfect for ski and adventure enthusiasts, offering a range of outdoor activities. Visitors can explore national and state parks, serene lakes, and nature reserves, making it a great spot for those seeking a mix of adventure and culture. Whether you're hitting the slopes or enjoying the breathtaking scenery, Hillsdale promises a memorable experience for all types of travellers.

  • National Shrine of the Divine Mercy: Located 20.9km from Hillsdale, this serene shrine offers a unique spiritual experience amidst beautiful surroundings. Visitors can engage in prayer, reflection, and admire the stunning architecture that reflects deep cultural significance.
  • Taconic State Park: Just 6.4km away, this national park is perfect for adventure enthusiasts. With its extensive hiking trails and breathtaking views, you can immerse yourself in nature, enjoy outdoor activities, and take in the picturesque scenery.
  • Copake Lake: Situated within Hillsdale, this lovely lake features a beautiful beach area, ideal for relaxation and romance. Enjoy outdoor activities like swimming or picnicking while soaking up the stunning views.

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 visit to Hillsdale, New York, you have several major airports to consider. Hartford, CT (BDL-Bradley Intl.) is 74.0km away, with nearby hotels like the 4-star Simsbury 1820 House and the 3.5-star Sheraton Hartford Hotel, both offering convenient access to the airport. Albany, NY (ALB-Albany Intl.) is 67.6km from Hillsdale, featuring quality accommodations such as The Landing Hotel at Rivers Casino & Resort and the DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 88.5km away, with options like the 3.5-star Thayer Hotel and the Crossroads Hotel, just 3.2km from the airport.

Frequently asked questions

Where is the best place to stay in Hillsdale?
Located 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Berkshires Untold and The Yankee Inn. See all available top hotels, or vacation rentals in Hillsdale.
What are some of the best holiday rentals that Hillsdale has to offer?
Cozy Riverside Berkshires Retreat: This holiday home rental outside of Hillsdale is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an electric kettle, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 family accommodation in Hillsdale?
Farm House Getaway on beautiful horse farm! is a country house with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Also, attractions in the area such as The Bookstore and Charles H. Baldwin & Sons are fun for children of all ages. Find more child-friendly accommodations in Hillsdale.
What's the best hotel for a romantic holiday in Hillsdale?
Farm House Getaway on beautiful horse farm! is a favourite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels 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?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn and The Red Lion Inn 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 67 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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