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A getaway from the bustle of city life, Berkshire has everything for a great romantic retreat for you and a loved one. Enjoy the pastoral scenery surrounded by the Berkshire Hills, and take a trip to the Clark Institute to enjoy some of the best in fine art. Within the quiet, quirky town of North Adams is The Porches Inn. This boutique inn is across the street from the Massachusetts Museum of Contemporary Art, and has whimsical decor and onsite gardens and a pool! Breakfast in the morning greets you at the Brook Farm Inn. Enjoy their library and their beautiful gardens, and go to the art galleries and the Ventfort Hall Mansion & Gilded Age Museum. The Lanesborough Country Inn gives you a relaxing and elegant vacation, where you'll enjoy the privacy of your own log cabin with a kitchenette. A complete romantic getaway awaits you and your loved one in Berkshire!

Showing 1-15 of 19 Romantic Resorts

Birchwood Inn

Lenox, Massachusetts, United States
$209
1-844-934-1851

Take a break from the stress of everyday life and treat your sweetheart to an unforgettable getaway. Stay in a luxurious king room with a comfortable... more

Resort features:
  • Family
  • Wedding
  • Nature
  • Romantic
  • Luxury
  • Mountain
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

The Inn at Stockbridge

Stockbridge, Massachusetts, United States
$150
1-888-466-7865

The Inn at Stockbridge is everything you're looking for in a relaxing and romantic getaway. Together with your sweetheart you can escape the... more

Resort features:
  • Golf
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns
  • Spa

The Cornell Inn Lenox

Lenox, Massachusetts, United States
$135
1-413-637-4800

Take your loved one to someplace special; a charming inn, surrounded by gardens and trees awaits at The Cornell Inn Lenox. This is a place that offers... more

Resort features:
  • Family
  • Reunions
  • Nature
  • Romantic
  • Ski/Snowboard
  • Historical
  • Boutique
  • Holiday
  • Bed & Breakfasts, Inns

Red Lion Inn

Stockbridge, Massachusetts, United States
$113
413-298-5545

From the moment you arrive at The Red Lion Inn, you and your sweetheart will fall in love with the old-world charm of this historic Massachusetts inn.... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

The Porches Inn

North Adams, Massachusetts, United States
$252
413.664.0400

Escape from the overwhelming crowds of the city and discover the quirky, artsy town of North Adams, Massachusetts when you stay at The Porches Inn.... more

Resort features:
  • Family
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Bed & Breakfasts, Inns

Brook Farm Inn

Lenox, Massachusetts, United States
$185
1 (413) 637-3013

Brook Farm Inn offers couples the chance to escape the hustle-bustle of everyday life. Here, you can take things as slow as you'd like with breakfast... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

Cranwell Spa & Golf Resort

Lenox, Massachusetts, United States
$195
1-800-272-6935

Whether relaxing together in your spacious suite, soaking in the outdoor pool, or enjoying a round of challenging onsite golf, you and your sweetheart... more

Resort features:
  • Family
  • Golf
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Health
  • Cabins, Cottages, and Chalets
  • Holiday
  • Spa

The Lanesborough Country Inn

Lanesborough, Massachusetts, United States
$69
1-413-442-1009

Fall in love all over again in the heart of the Berkshires! Lanesboro Country Inn offers a charming getaway for couples of all ages. You will love the... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Cabins, Cottages, and Chalets
  • Holiday
  • Bed & Breakfasts, Inns

Kemble Inn

Lenox, Massachusetts, United States
$200
1.800.353.4113

Fall in love all over again at the Kemble Inn, the ideal Berkshires destination. This charming inn offers stunning mountain views and a truly elegant... more

Resort features:
  • Meetings
  • Holiday
  • Honeymoon
  • Luxury
  • Romantic
  • Wedding

Brookside & Pondside Country Motel

Williamstown, Massachusetts, United States
$69
1-413-458-1896

Brookside & Pondside Country Motel offers natural beauty and country space that are perfect for couples seeking a romantic getaway. Featuring... more

Resort features:
  • Golf
  • Nature
  • Romantic

Maple Terrace Motel

Williamstown, Massachusetts, United States
$78
1-413-458-9677

Maple Terrace Motel is the right place to bring your sweetheart for a little getaway. The relaxing location surrounded by the Berkshires lets you... more

Resort features:
  • Romantic
  • Pet Friendly
  • Mountain
  • Honeymoon

Hampton Terrace Bed and Breakfast Inn

Lenox, Massachusetts, United States
$175
800.203.0656

Take an absolutely perfect Berkshire romantic getaway at the Hampton Terrace Bed & Breakfast Inn. Let the inn decorate your suite with flowers,... more

Resort features:
  • Historical
  • Holiday
  • Luxury
  • Romantic
  • Bed & Breakfasts, Inns

Shaker Mill Inn

West Stockbridge, Massachusetts, United States
$109
1-877-385-2484

For a romantic bed and breakfast retreat at Shaker Mill Inn, opt for one out of two suites equipped with a gas fireplace, or the Honeymoon Suite --... more

Resort features:
  • Honeymoon
  • Romantic
  • Ski/Snowboard

The Rookwood Inn

Lenox, Massachusetts, United States
$210
1-800-223-9750

Nothing says “I love you” more then a romantic escape for two! At The Rookwood Inn in Lenox, Massachusetts, select from one of the available... more

Resort features:
  • Meetings
  • Family
  • Pet Friendly
  • Romantic
  • Wedding

Black Swan Inn

Lee, Massachusetts, United States
$150
+1 (413) 243-2700

Spend some time with your better half. Leave the hustle of your daily grind and relax at Black Swan Inn in Lee, Massachusetts. On the foothills of the... more

Resort features:
  • Family
  • Romantic
  • Ski/Snowboard
  • Luxury
  • Mountain
  • Lake
  • Honeymoon

Showing 1-15 of 19 Romantic Resorts

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