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
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Hillsdale family-friendly hotels

1. 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.
€76
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires

2. 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.
€186
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville
€192
includes taxes & fees
31 Aug - 1 Sept
Changing Times Boutique Country Lodging

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
€136
includes taxes & fees
31 Aug - 1 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC

5. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
  • Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
€68
includes taxes & fees
9 Sept - 10 Sept
Econo Lodge Lee - Great Barrington

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
€122
includes taxes & fees
15 Sept - 16 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

7. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
€109
includes taxes & fees
9 Sept - 10 Sept
Best Western Plus Berkshire Hills Inn & Suites

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
€129
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

9. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
€273
includes taxes & fees
4 Sept - 5 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.

10. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
€332
includes taxes & fees
23 Sept - 24 Sept
Hudson NY’S Country Serenity Guest Suite.
View all properties

Choose what matters most at family-friendly hotels in Hillsdale

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillsdale Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Fine place to stay in the Lenox area."
Anthony 1-night trip
Posted 5 hours ago
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"If you're looking for a nice basic hotel with breakfast and free parking, I highly recommend this Quality Inn in Great Barrington, MA. Our room was clean, comfortable, and well priced. Breakfast included a nice variety of hot and cold food items. The scrambled eggs and sausage links were very tasty, and so were the make-your-own waffles. The staff were very nice. I look forward to returning. Note: A freight rail line runs through Great Barrington once a day."
Roberta 1-night trip
Posted 11 hours ago
Quality Inn Great Barrington
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"Very great stay and cleanest!"
Nancy 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Saugerties
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
St. Charles Hotel

St. Charles Hotel

8/10 Good
"A no-frills hotel, but super pet-friendly and with the friendliest , most helpful staff. Very close to Warren St,ots of shops and restaurants around!"
Gabriela 1-night trip
Posted 2 days ago
St. Charles Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 3 days ago
The Yankee Inn
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 3 days ago
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Lenox

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.