Explore 46 Luxury Hotels in The Berkshires
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Best Luxury Hotels in The Berkshires
Hotel On North
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is $130 per night from Apr 6 to Apr 7
$130
includes taxes & fees
$116 per night
Apr 6 - Apr 7
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, dry ...
9.4/10 Exceptional! (697 reviews)
"Staff was very helpful and kind"
Reviewed on Mar 28, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
The price is $513 per night from Apr 3 to Apr 4
$513
includes taxes & fees
$460 per night
Apr 3 - Apr 4
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
9.2/10 Wonderful! (80 reviews)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."
Reviewed on Jul 27, 2024
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $99 per night from Apr 9 to Apr 10
$99
includes taxes & fees
$88 per night
Apr 9 - Apr 10
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
9/10 Wonderful! (1,002 reviews)
"We highly recommend it!! My husband go there often for work and we usually stayed there. Very nice place!!"
Reviewed on Mar 28, 2025
Save an average of 15% on thousands of hotels when you're signed in
The Orchards Hotel
222 Adams Rd, Williamstown, MA
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal ...
8.4/10 Very Good! (441 reviews)
"A little dated. Restaurant shut down for renovations, disappointing"
Reviewed on Mar 9, 2020
Lantern House Motel
256 Stockbridge Road, Great Barrington, MA
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and a picnic area are also provided.
8.2/10 Very Good! (454 reviews)
Avoid staying here if you can.
"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 ..."
Reviewed on Nov 22, 2021
Sunset Inn
150 Housatonic Street, Lee, MA
The price is $94 per night from Apr 22 to Apr 23
$94
includes taxes & fees
$84 per night
Apr 22 - Apr 23
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area and express check-out are also ...
7.4/10 Good! (380 reviews)
A great price and perfect for our stay
"The room was clean and perfect for our stay."
Reviewed on Mar 18, 2025
Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is $66 per night from Apr 3 to Apr 4
$66
includes taxes & fees
$59 per night
Apr 3 - Apr 4
A hot tub is featured at this motel, along with free self parking. WiFi in public areas is free. Express check-out is also provided.
7/10 Good! (600 reviews)
"Great location. Pleasant staff."
Reviewed on Oct 13, 2024
1896 House Country Inn & Motels
910 Cold Spring Road, Williamstown, MA
The price is $127 per night from Apr 23 to Apr 24
$127
includes taxes & fees
$113 per night
Apr 23 - Apr 24
A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...
6.4/10 (328 reviews)
"Great"
Reviewed on Jan 25, 2025
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.
More 4 star hotels in The Berkshires
General Williams Estate House Lenox/Stockbridge
Stockbridge
9.6/10 Exceptional! (100 reviews)
Garden Gables Inn
135 Main St, Lenox, MA
9.2/10 Wonderful! (57 reviews)
The Berkshires Luxury Hotels
Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the The Berkshires luxury hotels are the plush oasis you’ve been looking for.
Choose from the best luxury hotels in The Berkshires to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.
We want you to enjoy your next vacation in style and the top luxury resorts in The Berkshires will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in The Berkshires, and plan your next opulent escape.
The Berkshires hotels essential information
Accommodation | 1,060 hotels |
|---|---|
Lowest Price | $66 |
Highest Price | $513 |
Popular hotels | The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Orchards Hotel, Lantern House Motel, Wagon Wheel Inn, Hotel On North, 1896 House Country Inn & Motels, The Yankee, Trademark Collection by Wyndham, Sunset Inn |
Popular Luxury Stays in The Berkshires
Popular places to visit
Tanglewood Music Center
5/5(150 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
Jiminy Peak Mountain Resort
4.5/5(98 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.
Mount Greylock
4.5/5(91 reviews)
Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.
Recent The Berkshires Hotel Reviews By Fellow Wanderers
Hotel On North
5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Staff was very helpful and kind"
A verified traveler stayed at Hotel On North
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 6 days ago
Travelocity Verified Review
"We highly recommend it!! My husband go there often for work and we usually stayed there. Very nice place!! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
5 out of 5
Posted 7 days ago
Travelocity Verified Review
"The location to jimney peak was great."
A verified traveler stayed at Vacation Village in the Berkshires
Explore More Ways to Travel with Travelocity
Explore More Ways to Travel with Travelocity
- Explore More
- Other Hotel Types
- Other Accommodation Types
- Explore Neighborhoods in The Berkshires
- Luxury hotels in other cities
An attraction
- Hotels near Tanglewood Music Center
- Hotels near Jiminy Peak Mountain Resort
- Hotels near National Shrine of the Divine Mercy
- Hotels near Williams College
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Ski Butternut
- Hotels near The Clark Art Institute
- Hotels near Lee Premium Outlets
- Hotels near Norman Rockwell Museum
- Hotels near Mount Greylock
- Hotels near Jacob's Pillow
- Hotels near Bousquet Ski Area
- Hotels near The Mount
- Hotels near Naumkeag Museum
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near Hancock Shaker Village
- Hotels near Housatonic River Walk
- Hotels near Berkshire Botanical Garden
- Hotels near Williamstown Theatre Festival
- Hotels near Shakespeare and Company
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Natural Bridge State Park
- Hotels near Berkshire Museum
- Hotels near Otis Reservoir
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Pyramid Lake
- Hotels near Lake Mansfield Park
- Hotels near Wyndhurst Golf & Club
- Hotels near Housatonic River
- Hotels near Barrington Stage Company
- Hotels near Lenox Library
- Hotels near Sterling and Francine Clark Art Institute
- Hotels near Berkshire Mountain Country Store
- Hotels near Goose Pond Reservation
- Hotels near Brodie Mountain
- Hotels near Kennedy Park
- Hotels near Pleasant Valley Wilderness Sanctuary
- Hotels near Otis Ridge
- Hotels near Taconic Golf Club
- Hotels near Western Gateway Heritage State Park
Types of Hotels
- Hotels with Air Conditioning in The Berkshires
- Hotels with Restaurants in The Berkshires
- Hotels with Free Parking in The Berkshires
- Ski Resorts and Hotels in The Berkshires
- Historic Hotels in The Berkshires
- Kid Friendly Hotels in The Berkshires
- Hotels with Free Breakfast in The Berkshires
- Golf Resorts & Hotels in The Berkshires
- Adventure Hotels in The Berkshires
- Hotels with Shopping in The Berkshires
- Hotels with Pools in The Berkshires
- Convention Center Hotels in The Berkshires
- Hotels on the Lake in The Berkshires
- Hotels with Bar in The Berkshires
- Spa Resorts & Hotels in The Berkshires
- Romantic Getaways & Hotels in The Berkshires
- Cheap Hotels in The Berkshires
- Pet Friendly Hotels in The Berkshires
- Hotels with Balconies in The Berkshires
- Hotels with Hot Tubs in The Berkshires
- Winery Hotels in The Berkshires
- Hotels with a Gym in The Berkshires
- Hotel Wedding Venues in The Berkshires
- Beach Resorts & Hotels in The Berkshires
- Hotels with an Indoor Pool in The Berkshires
- Hotels with Room Service in The Berkshires
- Hotels with smoking rooms in The Berkshires
- Hotels with Tennis Courts in The Berkshires
- Arcade Hotels in The Berkshires
- Hotels with Suites in The Berkshires
- Hotels with Kitchenettes in The Berkshires
- Hotels with Childcare in The Berkshires
- Boutique Hotels in The Berkshires
- Fishing Resorts & Hotels in The Berkshires
- Hotels with Airport Transfers in The Berkshires
- Oceanfront Hotels in The Berkshires
- Green Hotels in The Berkshires
- Hotels on the River in The Berkshires
- Hotels with a Lazy River in The Berkshires
- Casino Resorts & Hotels in The Berkshires
Areas of The Berkshires
- New England Hotels
- Upstate New York Hotels
- Lenox Hotels
- Northampton Hotels
- Williamstown Hotels
- The Catskills Hotels
- Hudson Hotels
- Rhinebeck Hotels
- Pittsfield Hotels
- Brattleboro Hotels
- Windsor Hotels
- Hudson Valley Hotels
- Great Barrington Hotels
- West Dover Hotels
- Troy Hotels
- Holyoke Hotels
- Stockbridge Hotels
- West Springfield Hotels
- Lee Hotels
- Bennington Hotels
- North Adams Hotels
- Wilmington Hotels
- Litchfield Hotels
- Greenfield Hotels
- Bloomfield Hotels
- Torrington Hotels
- Appalachian Mountains Hotels
- Avon Hotels
- Westfield Hotels
- Hancock Hotels
- Otis Hotels
- Red Hook Hotels
- Simsbury Hotels
- Western Massachusetts Hotels
- South Lee Hotels
- Coxsackie Hotels
- Rensselaer Hotels
- Lakeville Hotels
- Deerfield Hotels
- Charlemont Hotels
- New York City Luxury Hotels
- London Luxury Hotels
- Cabo San Lucas Luxury Hotels
- Los Angeles Luxury Hotels
- Las Vegas Luxury Hotels
- New Orleans Luxury Hotels
- Orlando Luxury Hotels
- Palm Springs Luxury Hotels
- Philadelphia Luxury Hotels
- Miami Luxury Hotels
- Atlanta Luxury Hotels
- Rome Luxury Hotels
- Sedona Luxury Hotels
- South Beach Luxury Hotels
- Bali Luxury Hotels
- Charleston Luxury Hotels
- Cancun Luxury Hotels
- Punta Cana Luxury Hotels
- Dallas Luxury Hotels
- Naples Luxury Hotels
More Ways To Wander The Berkshires
Most Popular
Hotels
Cape Cod Hotels with an Indoor PoolMartha's Vineyard Beach Resorts & HotelsCape Cod Casino Resorts & HotelsCape Cod Beach Resorts & HotelsWestern Massachusetts Hotels with Hot TubsCheap Hotels in North ShoreCape Cod Kid Friendly HotelsCape Cod Luxury HotelsCheap Hotels in Cape CodMartha's Vineyard Cheap HotelsCape Cod Hotels with Hot TubsWestern Massachusetts Golf Resorts & HotelsNorth Shore Luxury HotelsCheap Hotels in Nantucket IslandNorth Shore Hotels with Hot TubsCape Cod All Inclusive Resorts & HotelsCheap Hotels in Western MassachusettsCape Cod Pet Friendly HotelsCheap Hotels in Martha's Vineyard
Vacation Rentals