Hillsdale Hotel & Accommodation Deals 2026 from NZ$109 - Fully Refundable Options

A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Our top choices for Hillsdale hotels

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

A snow-covered landscape with a house and a sign that reads "the brooks".

1. The Brooks Motel

Hillsdale

Nelson

NZ$290

includes taxes & fees

21 Oct - 22 Oct

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A house with a stone patio and wooden stools.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

2. Little Cat Lodge

Copake Falls

Kees

NZ$304

includes taxes & fees

2 Nov - 3 Nov

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

3. Quality Inn Great Barrington

Great Barrington

Joan

NZ$152

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A kitchenette with a microwave, coffee maker, and coffee cups.

A hotel room with two beds, a desk, a TV, and a window with curtains.

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

NZ$203

includes taxes & fees

25 Oct - 26 Oct

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

5. the Alander

Copake

Thomas

NZ$288

includes taxes & fees

20 Oct - 21 Oct

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Bruce

NZ$285

includes taxes & fees

2 Nov - 3 Nov

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden wall with a white pendant light fixture.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

7. Prospect Berkshires

Egremont

Conor

NZ$676

includes taxes & fees

2 Nov - 3 Nov

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

8. Monument Mountain Motel

Great Barrington

Andrea

NZ$119

includes taxes & fees

1 Nov - 2 Nov

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

9. The Little Lion

Great Barrington

Lidia

NZ$206

includes taxes & fees

21 Oct - 22 Oct

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

10. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

NZ$157

includes taxes & fees

18 Oct - 19 Oct

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

11. East Rock Inn

Great Barrington

ERIK

NZ$289

includes taxes & fees

7 Nov - 8 Nov

A red building with a sign reading "Shaker Mill Inn."

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

12. Shaker Mill Inn

West Stockbridge

Mervin

NZ$270

includes taxes & fees

1 Nov - 2 Nov

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

13. Granville House

Housatonic

Marcia

NZ$504

includes taxes & fees

18 Oct - 19 Oct

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

14. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Bob

NZ$231

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

15. Quality Inn Lee - Lenox South

Lee

Christine

NZ$184

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a built-in oven, microwave, and stainless steel range hood.

A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

An outdoor seating area with a stone table and wicker furniture.

A hallway with a staircase, a framed painting, a mirror, and a potted plant.

16. Howard Hotel

Hudson

Elizabeth

NZ$206

includes taxes & fees

2 Nov - 3 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A covered porch with wicker furniture and hanging flower baskets.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

17. The Red Lion Inn

Stockbridge

Stephan

NZ$401

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A wooden deck with a staircase leading to a covered porch.

A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

A cozy living room with a gray sofa, wooden ceiling beams, a black TV stand, and a dining area with a table and chairs.

18. Micosta Leisure Inn

Hudson

Kim

NZ$199

includes taxes & fees

2 Nov - 3 Nov

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

A two-story house with a porch, a front door, and a mailbox.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

A room with a white door, a window, and a wall with various framed pictures.

19. Changing Times Boutique Country Lodging

Craryville

Thomas

NZ$398

includes taxes & fees

13 Oct - 14 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

20. The Yankee Inn

Lenox

William

NZ$211

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 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.

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Hillsdale Town Hall

This historic former library now serves as Hillsdale's administrative centre with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.

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Community Library

The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.

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Mosquito Island

Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.

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Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.

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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

A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top Hillsdale Hotel Reviews

Recent Reviews in Hillsdale

Berkshire Mountain Lodge

10/10 Excellent

"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"

Quality Inn Lee - Lenox South

8/10 Good

"Wonderful location. Nearby Norman Rockwell museum. Perfect for a stopover."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Nice little cabin, well situated to sightseeing"

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Went here for our 24th Wedding Anniversary!! We picked the area so we could go to the Norman Rockwell museum. To our surprise we were upgraded to a Villa. Thank you so much Becky for the accommodations. We will be back!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"

Pocketbook Hotel and Bath

8/10 Good

"."

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. We will be back!"

St. Charles Hotel

8/10 Good

"The St. Charles hotel is a good place to stay if you are looking for a great location to stay. It's within walking distance of restaurants and close to places to visit. However the WiFi network does kick out a lot."

More cheap accommodation in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

NZ$109

25 Oct - 26 Oct

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

NZ$152

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

NZ$205

4 Nov - 5 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

NZ$211

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

St. Charles Hotel

16 Park Place Hudson NY

NZ$301

22 Oct - 23 Oct

includes taxes & fees

6.6/10 (990 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

NZ$486

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (87 reviews)

Frequently asked questions

What is the best area to stay in Hillsdale?

The best area to stay in Hillsdale is in and around the town centre, particularly near the intersection of Routes 23 and 22.This area is the heart of Hillsdale, where you'll find the majority of the town's shops, eateries, and local services. It's quite walkable, making it easy to pop into a cafe, browse a boutique, or pick up essentials. The general layout is a classic small-town main street, with buildings lining the roads and a few side streets branching off.Couples looking for a relaxing getaway often find this area ideal. It offers easy access to local establishments for dining and drinks, and many accommodations in this central zone provide a comfortable base for exploring the surrounding countryside or simply enjoying a quiet weekend.For those seeking a more secluded experience but still wanting to be close to amenities, staying slightly outside the immediate town centre, perhaps a short drive along Route 23 towards Catamount Mountain, can be a good option.

What are the best hotels in Hillsdale that travellers recommend?

For a highly recommended hotel in Hillsdale, consider The Brooks Motel.The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with the modern and clean rooms. The customer service also receives excellent remarks. For those interested in outdoor activities, the motel is conveniently located near a ski area and Catamount Aerial Adventure Park, which is just 2.0 km away. The rooms feature premium bedding, Egyptian cotton sheets, and air conditioning, with some even offering a fireplace.

What are the best budget hotels in Hillsdale?

For a highly-rated budget hotel in Hillsdale, consider The Brooks Motel.The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with modern and clean rooms. The customer service also receives excellent feedback. This motel offers useful amenities such as free WiFi and complimentary toiletries. For those interested in winter sports, there are ski areas, ski lifts, ski runs, and cross-country skiing all conveniently located nearby. Pets are also welcome to stay free of charge, and free self-parking is available.

What are the best hotels in Hillsdale near Catamount Aerial Adventure Park?

For a well-located hotel near Catamount Aerial Adventure Park in Hillsdale, The Brooks Motel is a highly-rated option.The Brooks Motel, with a 7.4 rating, is conveniently situated just 2.0 km from Catamount Aerial Adventure Park. This motel is particularly suitable for families and offers a range of amenities including free WiFi, free self-parking, and complimentary toiletries. Guests frequently praise the super comfy and clean beds, the modern and clean rooms, and the excellent customer service. For those interested in winter sports, the motel is also very close to various ski facilities, including ski areas, lifts, runs, downhill, and cross-country options. Additionally, it features kitchens in its rooms and welcomes pets at no extra charge.

When is the best time to go to Hillsdale?

The best time to visit Hillsdale is during the summer (June to August) for outdoor activities and autumn (September to October) for the stunning fall foliage.Summer in Hillsdale offers warm, sunny days superb for enjoying the natural beauty of the region. This is an ideal time for couples and families who want to explore hiking trails, visit local farms, or enjoy swimming in nearby lakes. The weather is generally pleasant for outdoor dining and wandering through the small town centre.Autumn transforms Hillsdale into a picturesque landscape, with the surrounding hills ablaze with red, orange, and gold leaves. This season is particularly popular with couples seeking a romantic getaway and anyone who appreciates scenic drives and photography.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 hotel booking in Hillsdale with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Hillsdale hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Hillsdale?

Prices for hotels in Hillsdale often vary, but you can find a great deal from NZ$109 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 our cheapest rates.

Explore a world of travel with Expedia

Book Hotels in Hillsdale on Expedia.com

Search Hillsdale hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillsdale

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Hillsdale hotels

1. The Brooks Motel

2. Little Cat Lodge

3. Quality Inn Great Barrington

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

5. the Alander

6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

7. Prospect Berkshires

8. Monument Mountain Motel

9. The Little Lion

10. Travelodge by Wyndham Great Barrington Berkshires

11. East Rock Inn

12. Shaker Mill Inn

13. Granville House

14. The Black Swan Lee - Lenox, an Ascend Collection Hotel

15. Quality Inn Lee - Lenox South

16. Howard Hotel

17. The Red Lion Inn

18. Micosta Leisure Inn

19. Changing Times Boutique Country Lodging

20. The Yankee Inn

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Community Library

Mosquito Island

Roe Jan Brewing Co.

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Recent Reviews in Hillsdale

Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Cornell Inn, Lenox & The Berkshires

Pocketbook Hotel and Bath

Hotel On North

St. Charles Hotel

More cheap accommodation in Hillsdale

FairBridge Inn Express

Quality Inn Great Barrington

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

The Yankee Inn

St. Charles Hotel

Pocketbook Hotel and Bath

Frequently asked questions

Explore a world of travel with Expedia

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