Find Luxury Hotels in The Berkshires, MA

    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

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sep - 7 Sep

Top The Berkshires Luxury Hotels

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

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 AED 1,137
AED 1,375 total
includes taxes & fees
23 Sep - 24 Sep
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, (624)
"Convenient location for my trip"
The price is AED 400
AED 447 total
includes taxes & fees
1 Sep - 2 Sep
Wagon Wheel Inn
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (761)
"Quite and good location to around towns"
The price is AED 584
AED 652 total
includes taxes & fees
28 Sep - 29 Sep
Hotel On North
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (436)
"I've stayed there before when there were different owners. Thy were way more professional and accessible. "
1896 House Country Inn & Motels
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1008)
"Wonderful place to stay"
The price is AED 440
AED 491 total
includes taxes & fees
1 Sep - 2 Sep
The Yankee, Trademark Collection by Wyndham
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (402)
"No frills but it was a great stay!"
The price is AED 384
AED 429 total
includes taxes & fees
2 Sep - 3 Sep
Sunset Inn
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (572)
"Excellent place. Bountiful view. "
The price is AED 459
AED 513 total
includes taxes & fees
7 Sep - 8 Sep
Maple Terrace Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is AED 290
AED 324 total
includes taxes & fees
1 Sep - 2 Sep
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.

Luxury 4-star hotels in The Berkshires

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (491)
The price is AED 762
AED 851 total
includes taxes & fees
15 Sep - 16 Sep
The Williams Inn
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia