Title: Book the Best Stockbridge LUXURY Hotels - Upscale Hotels in Stockbridge, MA | Expedia.ca [Stockbridge Travel Guide](https://expedia.ca/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Vacation Rentals in Stockbridge](https://expedia.ca/Stockbridge-Vacation-Rentals.d162575.Travel-Guide-VacationRentals)[Flights to Stockbridge](https://expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)[Stockbridge Vacation Packages](https://expedia.ca/Stockbridge.d162575.Destination-Travel-Guides) ![Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA. Significant collection of the artist's original work & memorabilia on display in his hometown.](https://images.trvl-media.com/place/162575/de09378b-b417-4c3e-9c9a-1f58d65ad2fd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by William Keller ![](https://images.trvl-media.com/place/162575/de09378b-b417-4c3e-9c9a-1f58d65ad2fd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Stockbridge Luxury Hotels Tonight [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-22&endDate=2026-01-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-23&endDate=2026-01-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-23&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Stockbridge luxury hotels ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $428 CA $518 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (290 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $181 CA $213 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/8d37b75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (354 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $130 CA $145 total includes taxes & fees Feb 19 - Feb 20 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #10 Queen's Cottage | Living room](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (134 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/f5dca788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby CA $318 CA $356 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $581 CA $649 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Thayer House, Room 201, 1 King bed, Jetted tub](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/f1d5c4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Thayer House, Room 201, 1 King bed, Jetted tub | Living area](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/05269ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/755fb8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Inn On The Green [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) Great Barrington 9.2/10 Wonderful (90 reviews) "Beautiful Inn and outstanding chef" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $422 CA $509 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06®ionId=162575&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Find out more about Stockbridge ### Stockbridgeand its attractions for luxury travelers Stockbridge, Massachusetts, is a hidden gem for luxury travellers seeking a blend of culture, nature, and relaxation. Start your journey at the Norman Rockwell Museum, where you can admire the iconic works of the beloved American illustrator in a beautiful setting, perfect for art enthusiasts. Next, indulge in a serene afternoon at the elegant Kripalu Centre for Yoga & Health, offering world-class wellness programmes and spa treatments that cater to your need for rejuvenation. For those who enjoy the outdoors, the nearby Berkshire Botanical Garden provides a stunning backdrop for a leisurely stroll among diverse flora, ideal for a family outing. Don’t miss a visit to Tanglewood, the summer home of the Boston Symphony Orchestra, where you can experience exquisite live performances in an enchanting open-air venue. Finally, explore the charming streets of Stockbridge, dotted with boutique shops and fine dining options that offer locally-sourced cuisine. For luxury hotels, consider staying at the historic Red Lion Inn, where you can relish in the rustic elegance of its rooms while enjoying top hospitality. The inn's nearby key attractions makes it a perfect base for your explorations, allowing you to immerse yourself fully in the rich tapestry of Stockbridge. ### Find the best luxury hotels and resorts in Stockbridge For those seeking an indulgent escape in Stockbridge, Massachusetts, these exquisite hotels offer a blend of comfort and elegance, perfect for a luxurious getaway. [**The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood**](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) - **Why it's great for a luxury retreat:** The Stockbridge Country Inn stands out as a luxurious boutique experience, rated highly at 9.2, and offers guests an intimate and refined atmosphere. With amenities such as a private chef and resort views, this charming B&B is perfect for those seeking a personal touch. Guests can enjoy the warmth of their rooms, enhanced by plush premium bedding and luxurious bathrobes. - **Other amenities:** Beyond its luxurious accommodations, the inn provides a complimentary full breakfast daily, ensuring guests start their day in style. The hotel boasts an onsite art gallery, terrace for relaxation, and easy access to hiking and biking trails. With self-parking available, guests can explore the nearby Norman Rockwell Museum and the scenic landscapes surrounding the inn, making it a fantastic base for cultural adventures. - **Nearby attractions:** Housatonic River - 0.1 km, Chesterwood - 1 km, Norman Rockwell Museum - 1.5 km [**The Red Lion Inn**](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) - **Why it's great for a luxury retreat:** The Red Lion Inn perfectly embodies luxury with its charming historic character and elegant amenities, making it an ideal choice for travelers. With a strong review rating of 8.8, guests can enjoy romantic evenings by the fireplace and indulge in couples dining experiences. The Inn also offers 24-hour room service and luxurious Frette Italian sheets for an exceptional stay. - **Other amenities:** In addition to its luxurious offerings, The Red Lion Inn features outdoor pool access for relaxation, a spa providing rejuvenating treatments, and evening entertainment for delightful nights. Guests can also take advantage of concierge services, daily housekeeping, and complimentary toiletries to enhance their experience. The hotel is situated near various outdoor activities, including hiking, skiing, and snowboarding, allowing travelers to immerse themselves in the natural beauty of the region. - **Nearby attractions:** Housatonic River - 0.2 km, Berkshire Theatre Festival - 0.8 km, Naumkeag Museum - 1 km ## Top Stockbridge Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great property, very accommodating. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Room is great for families. Bit dated but clean and spacious." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "generally good" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Everything was very good. The room was clean and cozy." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Very clean...i dotted and t crossed" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "It’s an older property, but clean and comfortable. The staff was extremely friendly and welcoming. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Great place to stay if you enjoy paying less money and still sleeping well. Inexpensive, clean, quiet, and ridiculously convenient—just a short two-block stroll to the downtown strip for shopping and restaurants (close enough to walk, far enough to avoid the noise). Only 2.5 miles down a local road to Butternut ski mountain, so you’ll be on the slopes before your coffee fully kicks in. CVS shares the same parking lot, which is perfect in case you forget toothpaste, sunscreen, or your dignity. Most importantly—and let’s be honest, this matters—a beer, wine, liquor, and cheese shop is only one mile down the road. Priorities are clearly respected here. Rooms are clean, beds are super comfortable, and the décor politely reminds you that time exists. Free breakfast is solid but not life-changing: eggs, toast, sausage, waffles, yogurt, coffee, fruit—everything you need to function, nothing you’ll write poetry about. Bathroom fans are loud, but they drown out the 1 time per day freight train in the back yard, so net positive. Overall, a great stay, and for the cheap nightly price, it’s basically unbeatable unless you’re expecting chandeliers and a personal butler. Enjoy! " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ## Frequently asked questions ### What are the top-rated luxury hotels in Stockbridge? > This 4.5-star inn, with a 9.2 rating, offers premium bedding, air conditioning, and fireplaces for guest comfort. Its unique features include an onsite art gallery and the availability of a private chef, alongside its convenient location near the Norman Rockwell Museum and Chesterwood. ### Which area of Stockbridge is best to stay in for luxury hotels? > Main Street in Stockbridge is the central thoroughfare of the village, known for its quintessential New England charm. It's lined with historic buildings, art galleries, and independent shops, all within a short stroll of each other. The iconic Red Lion Inn is a prominent landmark here, anchoring much of the village's activity. > > > Couples looking for a refined and relaxing getaway will find this area particularly appealing. The high-end hotels here often feature fine dining, spa services, and beautifully appointed rooms. ### How much does a luxury hotel in Stockbridge cost? ### What are the best luxury hotels in Stockbridge with a pool? > The 4.5-star Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, with a 9.2 rating, offers an outdoor seasonal pool. Guests frequently comment on its premium bedding and the presence of amenities such as fireplaces and private chefs. ### What luxury activities and experiences are there in Stockbridge? > This central area is the heart of Stockbridge, known for its quintessential New England charm. You'll find a collection of upscale inns, art galleries, and boutiques lining Main Street, often housed in beautifully preserved historic buildings. It's very walkable, allowing you to easily explore the village on foot. > > > Couples looking for a refined getaway will find this area particularly appealing. Many of the luxury inns offer amenities such as fine dining restaurants, spa services, and beautifully landscaped gardens. You can enjoy a leisurely stroll to the Norman Rockwell Museum or visit [The Red Lion Inn](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) for a classic cocktail, both iconic Stockbridge experiences. > > > For those interested in the arts and culture, staying near the village centre provides easy access to the Berkshire Theatre Group's performances at The Unicorn Theatre or the Berkshire Botanical Garden, both just a short drive or pleasant walk away. ### How can I save on a luxury hotel in Stockbridge with Expedia? ### Is it cheaper to book a luxury Stockbridge hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Guest Houses in Alford ](https://www.expedia.ca/Alford-Guest-Houses.d3000421226-aaGuestHouses.Travel-Guide-Accommodation) - [Alford Hotels ](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - 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