Find luxury hotels in Great Barrington, MA

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Luxury Hotels

Next weekend
In two weeks

Our top choices for Great Barrington luxury hotels

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is £274
includes taxes & fees
10 Mar - 11 Mar
The Old Inn On The Green

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is £210
includes taxes & fees
1 Apr - 2 Apr
The Inn at Stockbridge

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (147 reviews)
"Such a cozy, authentic New England hotel, with all its charm. "
United States
Maulik
The price is £207
includes taxes & fees
8 Mar - 9 Mar
The White Hart

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (294 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is £118
includes taxes & fees
14 Mar - 15 Mar
Lakehouse Inn

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (11 reviews)
"Nice room. "
South Korea
JeongHoon
The price is £396
includes taxes & fees
29 Mar - 30 Mar
9 Academy

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is £256
includes taxes & fees
29 Mar - 30 Mar
Hampton Terrace Inn

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is £279
includes taxes & fees
21 Mar - 22 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is £91
includes taxes & fees
12 Mar - 13 Mar
The Central Downtown Inn & Suites

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is £391
includes taxes & fees
22 Mar - 23 Mar
33 Main
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.

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.

Find out more about Great Barrington

Great Barringtonand its attractions for luxury travelers

Great Barrington, Massachusetts, offers a blend of natural beauty and cultural richness that luxury travellers will find irresistible. Begin your exploration at the stunning Mahaiwe Performing Arts Center, where you can enjoy a diverse range of performances in an elegant, historic setting. For a touch of leisure, the nearby Butternut Ski Area provides excellent skiing and snowboarding options during the winter months, with upscale amenities to ensure a comfortable experience. Art enthusiasts will appreciate the contemporary works on display at the Berkshire Museum, which also features a charming café perfect for a leisurely lunch. Outdoor lovers can hike the picturesque trails of Monument Mountain, offering breathtaking views that are especially delightful in the autumn foliage. Finally, the vibrant downtown area boasts an array of boutique shops and gourmet restaurants, ideal for indulging your palate after a day of exploration. For a luxurious stay, consider the hotels located in the heart of Great Barrington. Here, you can expect personalised service and thoughtfully designed accommodations that cater to your every need. Imagine unwinding in a plush suite with views of the surrounding hills, followed by a delightful dinner at a nearby fine dining hotel, where farm-to-table cuisine and exquisite wines await. With its unique blend of culture, nature, and elegance, Great Barrington is a destination that promises to pamper and inspire.

Find the best luxury hotels and resorts in Great Barrington

For travelers seeking an upscale experience in Great Barrington, Massachusetts, these two hotels offer unparalleled luxury and comfort. Each hotel boasts exquisite amenities designed to elevate your stay.

The Old Inn On The Green

  • Why it's great for a luxury retreat: The Old Inn On The Green is a luxurious haven for travellers, a perfect review rating of 9.2. Guests are treated to lavish amenities like deep soaking bathtubs and premium bedding, ensuring ultimate relaxation after a day of exploring. The inviting fireplace creates a cosy atmosphere, making it an ideal spot for a romantic getaway or peaceful retreat.
  • Other amenities: Beyond its sumptuous accommodations, The Old Inn On The Green features a beautiful terrace, perfect for enjoying fresh air and scenic views. Guests can indulge in complimentary breakfast options, including a continental spread, while the garden offers a tranquil space to unwind. Self-parking is available for ease of access, and daily housekeeping ensures a well-maintained environment throughout your stay. Each room also benefits from air conditioning and toiletries to enhance your comfort.
  • Nearby attractions: Questing - 4.1 km, Dry Hill - 4.5 km, New Marlborough Town Hall - 5.4 km

Gedney Farm

  • Why it's great for a luxury retreat: Gedney Farm stands out as a luxurious retreat, receiving an impressive guest review rating of 9.2. This charming hotel features upscale amenities such as air conditioning and a warm fireplace, creating a perfect ambiance for relaxation. Guests can enjoy meals at the on-site restaurant with stunning garden views, ensuring a delightful dining experience in a serene setting.
  • Other amenities: In addition to its luxurious offerings, Gedney Farm provides a range of features to enhance guests' stays. The hotel includes a lovely terrace for outdoor relaxation, alongside free daily breakfast options to start your day right. For those interested in winter sports, snowshoeing and skiing are available nearby, while self-parking ensures convenience during your stay. Daily housekeeping and complimentary toiletries add to the overall comfort and attention to detail that guests can expect.
  • Nearby attractions: Questing - 4.5 km, Dry Hill - 4.8 km, New Marlborough Town Hall - 5.8 km

Top Great Barrington Hotel Reviews

Frequently asked questions

What are the top-rated luxury hotels in Great Barrington?
In Great Barrington, The Old Inn On The Green stands out among the top-rated luxury hotels.

The 4-star Old Inn On The Green, with a 9.2 rating, is known for its complimentary continental breakfast and the comfort of deep soaking bathtubs available in its rooms. Customers frequently praise the wonderful and delicious food served here.
Which area of Great Barrington is best to stay in for luxury hotels?
The best area to stay in Great Barrington for luxury hotels is the town centre, particularly along Main Street and its immediate surroundings.

This area is the heart of Great Barrington, offering a blend of historic charm and modern conveniences. You'll find a selection of upscale hotels situated amongst boutique shops, art galleries, and acclaimed restaurants. The architecture is a mix of Victorian and Colonial styles, giving the town a distinctive New England feel. Everything is quite walkable, making it easy to explore the local offerings on foot.

Couples seeking a refined getaway will find the town centre particularly appealing. Many luxury hotels here offer high-end amenities like gourmet dining, well-appointed spas, and comfortable lounges, great for a relaxing escape.
How much does a luxury hotel in Great Barrington cost?
Luxury hotel prices in Great Barrington vary, but you can find a great deal from £54 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates.
Which luxury hotels in Great Barrington are good for families?
For families seeking luxury accommodation in Great Barrington, The Old Inn On The Green is a top recommendation.

The 4-star Old Inn On The Green, with a 9.2 rating, provides a comfortable stay with amenities such as air conditioning, fireplaces, and deep soaking bathtubs. Guests frequently praise the wonderful and delicious food, and the hotel offers complimentary continental breakfast.
What are the best luxury hotels in Great Barrington with a pool?
For a luxury hotel in Great Barrington featuring a pool, The Old Inn On The Green is an excellent option.

The 4-star Old Inn On The Green, with a 9.2 rating, offers a seasonal outdoor pool. Guests frequently praise the wonderful and delicious food served, and rooms include amenities such as premium bedding and a deep soaking bathtub. Complimentary continental breakfast is also provided.
What luxury activities and experiences are there in Great Barrington?
The best area to stay in Great Barrington for luxury activities and experiences is right in the town centre, particularly around Main Street and Railroad Street.

This area is the heart of Great Barrington, offering a blend of upscale dining, boutique shopping, and access to cultural venues. You'll find a selection of high-end restaurants focusing on farm-to-table cuisine, art galleries showcasing local and regional artists, and unique independent shops. The historic Mahaiwe Performing Arts Centre is also located here, hosting a variety of live performances.

Couples looking for a sophisticated getaway will find the town centre particularly appealing. You can easily stroll between gourmet restaurants for dinner, browse art galleries, or catch a show without needing to drive. Many of the most sought-after hotels and inns, which often feature amenities like spa services and fine dining, are also situated within easy walking distance of these attractions.

For those interested in outdoor pursuits combined with luxury, staying slightly outside the immediate town centre but within a short drive offers access to private estates and resorts that provide activities like guided fly-fishing, horse riding, or access to exclusive hiking trails.
How can I save on a luxury hotel in Great Barrington with Expedia?
There are plenty of ways to save on a luxury hotel in Great Barrington. Join One Key™, our free travel rewards programme, to unlock Member Prices across a range of hotels. Typically, booking in advance will help you save on hotel bookings. If you're feeling spontaneous, be sure to check for last-minute deals.
Is it cheaper to book a luxury Great Barrington hotel and flights as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my luxury hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Great Barrington for you.

Explore a world of travel with Expedia