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Filled with rich history, the Catskills Region of New York is home to the legendary town of Woodstock, the site of the famous music festival that took place in August of 1969. Staying at Twin Gables in Woodstock will offer full access to this famous town while providing great lodging options! Learn about Rip Van Winkle and visit the history trail while staying at Washington Irving Inn located in Hunter. Wolff’s Maple Breeze Resort in Catskill is located on Cauterskill Road, one of the oldest roads in America! It is very likely that George Washington crossed it at some point during the early years of the United States. To learn more about the rich history of this area, stay in the Catskills during your next New York historical getaway.

Showing 1-15 of 15 Historical Resorts

Villa Roma Resort and Conference Center

Callicoon, New York, United States
$150
1-866-452-9559

The Villa Roma has been around for a long time. When you stay here, learn about its humble beginnings as a small hotel-style bed & breakfast and... more

Resort features:
  • All-Inclusive
  • Family
  • Golf
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Ski/Snowboard
  • Pet Friendly
  • Luxury
  • Mountain
  • Lake
  • Historical
  • Honeymoon
  • Holiday
  • Spa
  • Timeshare
  • Villas and Condos

Rocking Horse Ranch Resort

Highland, New York, United States
$149
1-866-980-7688

When Rocking Horse Ranch Resort was first built in 1958, it offered a strong rustic environment and was truly centered around horses. While that all... more

Resort features:
  • All-Inclusive
  • Beach
  • Family
  • Meetings
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Mountain
  • Lake
  • Historical
  • Dude Ranch
  • Holiday
  • Spa
  • Villas and Condos
  • Waterpark

Winter Clove Inn

Round Top, New York, United States
$95
1-866-452-9609

Winter Clove Inn is more than a getaway; it's history is stemmed from the Revolutionary War. Once H.B. Whitcomb opened his farmhouse to summer guests,... more

Resort features:
  • All-Inclusive
  • Family
  • Golf
  • Reunions
  • Wedding
  • Nature
  • Romantic
  • Ski/Snowboard
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

Albergo Allegria

Windham, New York, United States
$99
1-866-520-6166

Listed on the National Register of Historical Places for Greene County, Albergo Allegria is fully restored to its former 1892 glory including the... more

Resort features:
  • Family
  • Golf
  • Nature
  • Romantic
  • Ski/Snowboard
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

Crystal Brook Resort

Round Top, New York, United States
$69
1-866-932-0522

The Catskill areas in New York have plenty of history surrounding them. While at the Crystal Brook Resort, ask the friendly staff for information on... more

Resort features:
  • All-Inclusive
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Ski/Snowboard
  • Mountain
  • Historical
  • Honeymoon
  • Holiday
  • Villas and Condos

The Mountain Brook

Tannersville, New York, United States
$150
1-866-708-9562

Built in 1940s, the The Mountain Brook represents the historic and architectural past of one of America's most distinctive regions. Today, it's the... more

Resort features:
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ski/Snowboard
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday

Baumann's Brookside Summer Resort

Greenville, New York, United States
$103
1-866-658-6039

History buffs will love planning a trip to Baumann's Brookside Summer Resort thanks to it's close proximity to so many historic mansions and museums.... more

Resort features:
  • All-Inclusive
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Mountain
  • Historical

Glen Falls House

Round Top, New York, United States
$67
1.866.822.5778

Vacation at the Glen Falls House and visit the many nearby historical sites. Thomas Cole House, Bronck Museum and Barns, Olana, and Clermont State... more

Resort features:
  • All-Inclusive
  • Cabins, Cottages, and Chalets
  • Family
  • Reunions
  • Golf
  • Historical
  • Nature
  • Wedding

Spillian

Fleischmanns, New York, United States

History buffs are sure to revel in the accommodations of Spillian! Each room takes on a different theme, each with furnishings and architectural... more

Resort features:
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Romantic
  • Ski/Snowboard
  • Historical
  • Villas and Condos

Beds on Clouds

Windham, New York, United States
$84
1-518-734-4692

This charming Victorian bed and breakfast was originally built in 1854, when Windham was called Osbornville, and was once home to Postmaster General... more

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

Andes Hotel and Restaurant

Andes, New York, United States
$85
1.845.676.3980

Walk along the trails of many that have come to the Catskills before. Writers, artists, painters, and nature enthusiasts have long come to admire the... more

Resort features:
  • Family
  • Fishing
  • Ski/Snowboard
  • Mountain
  • Historical

Catskill Lodge

Windham, New York, United States
$69
(518) 261-7150

Built in 1893, the Catskill Lodge has been recently renovated and gleams with historic splendor. Each room is a masterpiece of period decor; yet... more

Resort features:
  • Historical
  • Mountain
  • Nature
  • Ski/Snowboard

Twin Gables of Woodstock

Woodstock, New York, United States
$90
1-845-679-9479

Established in 1926, Twin Gables of Woodstock is the oldest Bed & Breakfast in the Woodstock area. The Victorian house features period furniture... more

Resort features:
  • Historical
  • Mountain
  • Nature
  • Romantic

Wolff's Maple Breeze Resort

Catskill, New York, United States
$151
1-800-777-9653

Wolff's Maple Breeze Resort has a long and rich history which they're proud to share. It is believed that the land on which it is situated was... more

Resort features:
  • All-Inclusive
  • Family
  • Reunions
  • Fishing
  • Historical
  • Holiday
  • Lake
  • Nature

Washington Irving Inn

Hunter, New York, United States
$140
1-518-589-5560

Built in the 1890s, the antique Washington Irving Inn is rich in architecture and named after one of America's earliest authors. Stay in the Rip Van... more

Resort features:
  • Historical
  • Honeymoon
  • Mountain
  • Nature
  • Romantic
  • Cabins, Cottages, and Chalets

Showing 1-15 of 15 Historical Resorts

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