Find & compare luxury hotels in Stockbridge, MA

Best Luxury Hotels in Stockbridge

Lakehouse Inn

615 Laurel St., Lee, MA

$135

per night

May 9 - May 10

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a snack bar/deli are also on offer.

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

Get rates

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.

33 Main

33 Main Street, Lenox, MA

$377

per night

May 1 - May 2

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A lobby fireplace, a communal living room, and express check-in are also on offer.

Granville House

98 Division St, Housatonic, MA

Free Cancellation

Reserve now, pay when you stay

$200

per night

Apr 29 - Apr 30

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free full breakfast is served. A picnic area and luggage storage are also provided.

Pet friendly

Breakfast included

The Barrington

281 Main St., Level 3, Great Barrington, MA

$325

per night

Apr 27 - Apr 28

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Express check-out, luggage storage, and concierge services are also on offer.

The Inn at Stockbridge

30 East Street, Stockbridge, MA

Get rates

This bed & breakfast features an outdoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

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

26 Glendale Road, RR 183, Stockbridge, MA

$401

per night

Apr 29 - Apr 30

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

Devonfield Inn B&B

85 Stockbridge Rd., Lee, MA

$279

per night

Apr 28 - Apr 29

An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi in public areas. A business center, a terrace, and a garden are also on offer.

Seven Hills Inn

40 Plunkett Street, Lenox, MA

Get rates

This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a garden, and a library are also on offer.

Don't see what you're looking for?

See all available properties in Stockbridge

View all properties

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 Stockbridge

The Old Inn On The Green

134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA

$265

per night

Apr 28 - Apr 29

9/10 Wonderful! (70 reviews)

Stockbridge 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 Stockbridge luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Stockbridge 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 Stockbridge will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Stockbridge, and plan your next opulent escape.

Stockbridge hotels essential information

Accommodation	1,246 hotels
Lowest Price	$135
Highest Price	$401
Popular hotels	Lakehouse Inn, The Central Downtown Inn & Suites, 33 Main, Granville House, The Barrington, The Inn at Stockbridge, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Devonfield Inn B&B, Seven Hills Inn

Recent Stockbridge Hotel Reviews By Fellow Wanderers

The Black Swan Lee - Lenox, Ascend Hotel Collection

5 out of 5

Posted 5 days ago

Travelocity Verified Review

"Michelle that checked us in was fantastic!!! The Indian restaurant on premises was great. Everything at the hotel was immaculate. "

A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

5 out of 5

Posted 10 days ago

Travelocity Verified Review

"I would highly recommend the Yankee. The front desk person was kind and welcoming. As soon as I opened the door to my room, I was pleased to see how clean and cozy it was. The breakfast room was well stocked, and the pool was being enjoyed by families with children. I would definitely stay again. The property is on a main road with easy access to shopping . The only downside was the noisy heater. But I was warm!! Many thanks to all who work diligently to keep the Yankee a pleasant place for travelers. "

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham