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

Hillsdale Hotel Guide - Family Friendly Hotels in Hillsdale, New York

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Check availability on Hillsdale Family Friendly Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Hillsdale family-friendly hotels

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A dining area with a wooden table, chairs, and a colorful striped rug.
A snow-covered landscape with a house and a sign that reads "the brooks".
A bathroom with an orange floral wallpaper, a round mirror, a white sink, and a coffee maker.

1. The Brooks Motel

The Brooks Motel
Hillsdale
€146
includes taxes & fees
9 Nov - 10 Nov
The Brooks Motel
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.
A room with a bed, a small table, and a chair. There is a window with blinds and a door leading to another room.
A bathroom with a blue wall, a white bathtub, a shower curtain, a stack of white towels on a shelf, and three black bottles on the wall.
A modern living room with a grey sofa, a patterned rug, and a dining area with orange chairs.

2. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
€175
includes taxes & fees
11 Oct - 12 Oct
The Brooks Motel: Exceptional Suite
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.
A cozy living room with a grey sofa, a wooden coffee table, a fireplace, and a television mounted above it.
A red cabin with a screened porch, a small deck, and a barbecue grill in a wooded area.
A wooden cabin with a porch, a grill, and a flower planter.

3. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
€349
includes taxes & fees
12 Oct - 13 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A two-story house with a front porch, surrounded by lush greenery and trees.
A bedroom with a bed centered under a black ceiling beam, flanked by two bedside tables with lamps, a window with a view of trees, and a radiator on the left wall.
A living room with a sofa, coffee table, and a colorful rug.
A wooden dining room with a large table and chairs, a colorful rug, and a staircase leading to another level.

4. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
€675
includes taxes & fees
11 Oct - 12 Oct
Perfect House In Hillsdale, Brings Friends & Fam
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A modern kitchen with white cabinets and a built-in knife block.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

5. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
€590
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A bathroom with a white tiled floor, a wooden vanity with drawers, a white toilet, a bathtub, and a shower with a handheld showerhead.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

6. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
€60
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
A modern hotel lobby with seating areas, tables, and a reception desk.
A modern bathroom with a large mirror, a sink, and a shower.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A hotel room with two beds, a desk, a TV, and a window with curtains.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
€93
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
€106
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A room with multiple arcade games, including 'American Idol' and 'Toy Taxi'.
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.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.
€143
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.
A modern bathroom with a white sink, a toilet, and a bathtub.

10. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
  • Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
€79
includes taxes & fees
18 Oct - 19 Oct
Travelodge by Wyndham Great Barrington Berkshires
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Choose what matters most at family-friendly hotels in Hillsdale

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillsdale Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night."
alan 1-night trip
Posted 21 hours ago
Hotel On North
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"
Woodward 2-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 2 days ago
The Yankee Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Nice Inn/B&B in Lenox MA, about a mile from downtown."
Anne 1-night trip
Posted 2 days ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

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!"
Joanne 1-night trip
Posted 3 days ago
The Red Lion Inn
St. Charles Hotel

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."
James 2-night trip
Posted 4 days ago
St. Charles Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 4 days ago
Quality Inn Great Barrington
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"The room was clean and staff very pleasant and helpful. I would stay again."
Shirley 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

What's Hillsdale like for family-friendly holidays?
The relaxing destination of Hillsdale is a great choice if you've been considering a holiday with the children. The horse riding, coffee shops and libraries are just a few things that make this an attractive spot for a family holiday. Take to the air and fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) from the city centre.
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.
When's the best time to book a family-friendly holiday 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.
What's there to see and do with your family in Hillsdale?
Catamount Ski Area, Roe Jan Brewing Co. and Community Library are interesting attractions that you and your family will enjoy exploring while you are staying in Hillsdale. Make sure that you have lots of time for activities such as Ski Butternut and Lake Taghkanic State Park.