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The Best Hotels in the Berkshire Hills

Doug Kerr via Flickr

The Berkshire Hills epitomise country life at its most idyllic. The landscape is serene and beautiful, with hills and mountains to add interest to the lush green. And there are miles of walking trails running all over them. But this is a place of cultured leisure, so there’s plenty to do too: world-class theatre and music festivals, great restaurants and some impressive museums. Our guide to the best hotels in the Berkshire Hills will give you ideas for the perfect bases from which to explore this glorious region.

Massachusetts Office of Travel

Some of the best hotels in the Berkshire Hills have been converted from the grand ‘cottages’ built by the well-to-do elite of Boston and New York, who have always come here to escape the city heat in summer. Our Guru’s recommendations for the best hotels in the Berkshire Hills also includes some spoiling spas and peaceful country inns.

Doug Kerr via Flickr

The Berkshires have been associated with New England and a tradition of idealism and intellectualism, which is why this relatively rural region has so many impressive museums, but being equidistant between Boston and New York, the culture has been gradually settling down to represent a mid point between both cities. Norman Rockwell’s Museum is just outside Stockbridge, his former home, and Tanglewood in Lenox is the summer home to the Boston Symphony Orchestra for example. Williamstown has a well known Shakespeare Company, plus the Clark Art Institute, a particularly beautiful and well appointed art museum.

Use our guide to the best hotels in the Berkshire Hills and start planning your trip now!

The Best Hotels in the Berkshire Hills

For stunning views


  • Wheatleigh is a magnificent 19th century château-style mansion with 19 rather grand rooms and a very good French restaurant. Set within its own 22 acres of grounds there is beauty wherever you look and plenty to do, including play golf, fish, go cycling or horse riding, or skiing, or even hot air ballooning.

The Most Romantic Hotels in the Berkshire Hills

Applegate Inn

  • The Applegate Inn in Lee is a period property with some lovely antique furnishings and fireplaces in each of the 11 bedrooms. There’s also beautiful gardens and a heated outdoor pool.
  • The Gateways Inn is an easy walk from downtown Lenox, with 11 Shakespeare themed bedrooms and an old world charm. There’s a great restaurant with live music.

For a complete escape


  • Ivy clad and castle-like, Blantyre, outside Lenox, is a grand hotel set on its own 220 acre estate. There are just 23 rooms, most with four-poster beds, chandeliers, antiques and floral fabrics, plus there’s a magnificent dining room and a luxurious spa.
  • The Inn at Stockbridge is a small, Georgian style mansion set in 12 acres of beautiful gardens. The 15 rooms and suites have antique furniture and elegant decor. The restaurant has its own kitchen gardens.
  • The Cranwell Resort, Spa and Golf Course is a Tudor style mansion surrounded by 380 acres of its own beautiful Berkshires land. As well as the stunning mountain views, the resort has 114 large, classic rooms, business and fitness facilities and a great spa and pool.

The Best Value Hotels in the Berkshire Hills

Red Lion Inn

  • The Red Lion Inn in Stockbridge is an historic boutique hotel with 108 rooms and wonderful New England hospitality. There’s an old world charm here, think birdcage lifts, antique furnishings, fireplaces and a grand piano. Plus the views are fantastic. Rooms start form around £120 per night.

Still not sure which of our Guru’s recommendations for the best hotels in the Berkshire Hills might be perfect for you? Contact one of our friendly Gurus for advice, or widen the net and check out all our Massachusetts recommendations.

  • Wheatleigh 19 rooms from £326


    Magnificent late 19th Century mansion in the beautiful scenery of Lenox, Massachusetts. The public and private rooms within this chateau-style hotel blend ornate grandeur with subtly modern furnishings. The French restaurant is the best in the area, and a lake and pool feature in the 22-acre grounds

    Active Holiday  -  Activites on offer include golf, horse riding, biking, fishing, hot-air ballooning and skiing.
    Country Escape  -  The hotel is set in 22 acres of landscaped gardens, and features an outdoor pool and a lake
    Swimming Pool  -  The outdoor swimming pool is hidden in the gardens, surrounded by leafy trees and colourful flowers
    Views  -  Great views from hotel
    Recommended by  -  Mr & Mrs Smith
    Check prices
  • Blantyre 23 rooms from £215


    Grand hotel set in a sprawling 220-acre estate just outside Lenox, Massachusetts. The ivy-clad, castle-like building features traditional rooms with four-poster beds, chandeliers, antiques and floral fabrics. The dining room is magnificent, the spa luxurious, and plenty of activities are on offer.

    Back to Nature  -  The hotel is set in a 220-acre country estate with woodland and manicured gardens, perfect for exploration and relaxation
    Active Holiday  -  The perfect active holiday- skiing, snow-shoeing, ice-skating, swimming, golf and tennis are all available on-site
    Country Escape  -  The ivy-clad building resembles a traditional English manor or castle on a sprawling estate
    Spa  -  The Potting Shed, featuring a greenhouse with a hot tub, steam room, sauna, outdoor pool, and an array of treatments
    Recommended by  -  Kiwi Collection, Mr & Mrs Smith, Tablet, Relais & Chateaux
    Check prices
  • The Inn at Stockbridge 15 rooms from £197


    A classic, Georgian-style House, set on 12 acres of beautiful gardens. Antique furnishing, elegant drapes and warm colours lend a romantic air to the suites. On-site restaurant uses produce fresh from the kitchen garden. Unwind in style.

    Great walks  -  Beautiful walks in the neary Berkshire Botanical Gardens.
    Sights nearby  -  Norman Rockwell Museum .
    Swimming Pool  -  Outdoor seasonal pool.
    Full of character
    Check prices
  • Applegate Inn 11 rooms from £161

    Lee, Massachusetts

    Built at the end of America’s 'Gilded Age', the Inn is a Select Registry property and the decor is in keeping with this period. Think antique furnishings and bedroom fireplaces. Enjoy the outdoor heated pool and beautiful gardens while lying in a hammock. Ultimate pampering and relaxation!

    Great walks  -  Great walking and hiking at Pleasant Valley Wildlife Sanctuary and Berkshire Scenic Treks & Canoe Tours.
    Swimming Pool  -  Outdoor, heated pool- seasonal.
    Full of character
    Romantic  -  Good for couples.
    Check prices
  • Cranwell Resort, Spa and Golf Course 114 rooms from £150

    Lenox (Massachusetts)

    Tudor-style mansion rests in 380 acres of the Berkshires offering exquisite service, activities and business and fitness facilities. Large classic rooms have balconies. Sloane’s Tavern is a casual eatery, Mansion Dining offers stunning mountain views. Much to do for all, or relax at the spa or pool.

    Secluded setting  -  For escaping.
    Views  -  Great views from hotel
    Romantic  -  Good for couples.
    Birdwatching  -  Good birding near the hotel.
    Check prices
  • The Red Lion Inn 108 rooms from £115

    Stockbridge (Massachusetts)

    1773 boutique welcomes guests with fireplace, grand piano and New England hospitality. Hop in the birdcage lift and enter old-world charm rooms with antique furnishings, large beds and modern bathrooms. Widow Bingham's Tavern and Lion's Den Pub both serve American dishes. A great countryside break.

    Towelling robes
    Romantic  -  Good for couples.
    Views  -  Great views from hotel
    Full of character
    Check prices
  • Gateways Inn 11 rooms from £138


    This luxurious Inn right in the heart of the action is an easy walk to downtown Lenox, and to live entertainment. The plush Shakespearean themed bedrooms furnished with antique pieces give an old world feel. Live musical performances enhance the already mouthwatering dining experience!

    Romantic  -  Good for couples.
    Full of character
    Four poster beds  -  For romantics.
    Quirky  -  An experience!
    Check prices


Written by Kat Parr Mackintosh

posted Monday, 28th November 2016
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