Best Luxury Hotels in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Luxury Hotels

Top The Berkshires Luxury Hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is RM1,661
RM2,009 total
includes taxes & fees
26 Aug - 27 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel
Terrace/patio

The Orchards Hotel

2.5 star property
8.6 out of 10, Excellent, (442)
The Orchards Hotel
Lantern House Motel
Gazebo

Lantern House Motel

2.5 star property
8.2 out of 10, Very good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (617)
"Convenient location for my trip"
The price is RM292
RM326 total
includes taxes & fees
14 Aug - 15 Aug
Wagon Wheel Inn
Hotel On North
Lobby lounge

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (752)
"Staff were excellent and welcoming."
The price is RM802
RM896 total
includes taxes & fees
14 Aug - 15 Aug
Hotel On North
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (432)
"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"
1896 House Country Inn & Motels
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is RM568
RM634 total
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (400)
"No frills but it was a great stay!"
The price is RM466
RM520 total
includes taxes & fees
26 Aug - 27 Aug
Sunset Inn
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (568)
"The staff, room and property was wonderful! "
The price is RM476
RM532 total
includes taxes & fees
4 Sept - 5 Sept
Maple Terrace Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (782)
"My stay was perfect. I can't wait to stay there again. "
The price is RM334
RM374 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham 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.

Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"A"
Carolyn 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham