These grand historic resorts are outstanding choices for family reunions and multi-generational celebrations, offering a wealth of activities for all ages
Finding the perfect site for luxury multi-generational family vacations and celebrations is an essential part of travel planning. It’s important to identify a resort that the whole family will love.
All generations will enjoy reuniting and creating lifelong memories at the nation’s leading historic luxury resorts featuring an unforgettable blend of exquisite accommodations, stunning architecture, family-friendly activities and rich stories of their own. These legendary destination resorts offer opportunities to reconnect and enjoy shared experiences in settings filled with beautiful scenery, timeless elegance and an extraordinary sense of place.
Here are 11 grand family resorts to consider for your next multi-generational trip.
Chatham Bars Inn, Massachusetts
Beach destinations are popular choices for family reunions and multi-generational trips. Located on 25 oceanfront acres in Cape Cod, the award-winning Chatham Bars Inn has been a favorite choice for seaside family getaways since opening in 1914. Set on a quarter-mile private beach, the idyllic historic property offers a wide variety of recreational activities and beautifully decorated rooms and suites with stunning views.
The Chatham Bars Inn’s Kids Crew programs and Night Owls sessions for children ages 4-12 are available during the summer months, and exciting activities are also available for older kids. Family members can choose accommodations in the resort’s historic main inn or luxurious cottages and spa suites. The Forbes Five-Star Chatham Bars Inn features multiple dining options, and the hotel’s eight-acre produce farm is available to visit. Fun-filled activities include biking, tennis, swimming, whale-watching, sailing, and other adventures.
The Broadmoor, Colorado
The Broadmoor is an extraordinary luxury destination for family vacations and multi-generational celebrations. The historic Colorado Springs property first welcomed guests in 1918, and its iconic legacy continues as the world’s longest-running Forbes Five-Star and AAA Five Diamond resort. Stretching across 5,000 acres, The Broadmoor caters to multi-generational groups with lavish accommodations, outstanding dining venues, and an extensive array of amenities for all ages and interests.
Multi-generational families can choose from The Broadmoor’s 784 beautifully appointed rooms, suites, and cottages. The resort also operates three all-inclusive Wilderness Experiences well-suited for family reunions: the Orvis-endorsed Fly Fishing Camp, The Ranch at Emerald Valley and the mountaintop Cloud Camp, set at 9,000 feet. The Broadmoor features two championship golf courses, multiple pools, a world-class spa and fitness center, a nationally recognized tennis program, and a wide variety of activities, including mountain biking, hiking, pickleball, horseback riding and the seasonal Bee Bunch Children’s Camp for kids ages 3-11.
The Sagamore Resort, New York
Beautifully situated on its own private island, The Sagamore Resort has been catering to families since 1883. This gorgeous Lake George gem features grand public spaces, eight outstanding dining venues, and elegantly comfortable rooms and suites. The Sagamore’s multi-bedroom lodge condominiums and homes are also ideal for reuniting family groups.
The Sagamore’s lakefront setting amidst the splendor of the Adirondack Mountains provides 70 acres of fun with a wide array of year-round activities for families to enjoy. The award-winning luxury resort offers large indoor and outdoor pools, roped-off lake areas for swimming, golf, tennis, pickleball, fishing, hiking, sailing excursions on the resort’s 72-foot wooden touring vessel, and a superb spa and fitness center. The Sagamore’s 10,000-square-foot indoor Rec Center is loaded with games and attractions perfect for entertaining all ages. The resort’s concierge can help arrange additional activities and adventures in the Lake George area.
The Breakers, Florida
Founded in 1896 by Henry Flagler, The Breakers is set on 140 acres in Palm Beach, Florida. The oceanfront property is well-designed for multi-generational family vacations. Generations of upscale families have flocked to this amenity-packed luxury resort to start new traditions and make cherished memories together. This AAA Five Diamond Italian Renaissance-style masterpiece features 534 elegant guest rooms and suites, many with captivating views of the Atlantic Ocean. The Breakers’ intimate Flagler Club provides an even more luxurious, customized experience.
Attractions at The Breakers include multiple restaurants, an outstanding private beach club with four pools, an oceanfront fitness center, and an excellent spa. Sports-loving families will enjoy the two 18-hole golf courses, world-class tennis and racquet facilities, and on-site watersports. The Breakers’ massive indoor-outdoor Family Entertainment Center is designed specifically for families, offering the resort’s Italian Restaurant and activities and games for all ages. This family-friendly resort caters to little ones with complimentary baby equipment, childproofing services, and kids’ menus.
Omni Mount Washington Resort, New Hampshire
Constructed in 1902 by Joseph Stickney, the stately Omni Mount Washington Hotel has been the site of many multi-generational family celebrations and historic events. The famed National Historic Landmark hosted the Bretton Woods International Monetary Conference of 1944, and guests enjoy touring the property and exploring its fascinating heritage. The Omni Mount Washington Resort and its attractions have been beautifully enhanced over time, offering families an extensive array of accommodations, activities and dining options. Multi-generational groups often gather on the resort’s expansive porches, nostalgically reminiscing about past visits and enjoying breathtaking mountain views.
The AAA Four Diamond resort features spacious lodging options in its more exclusive Presidential Wing, as well as a variety of rooms and suites in the historic hotel and inn. Families can dine together in restaurants with delectable cuisine, including the Rosebrook Lodge venue atop the resort’s Bretton Woods Ski Area. Fun-filled activities at this magical family playground include championship golf, tennis, pickleball, swimming, horseback riding, hiking, canopy tours, mountain biking, fly-fishing, an innovative Omni Junior Chefs program, and skiing during the winter months.
Grand Hotel, Michigan
Opened in 1887 and accessible only by ferry or plane, the legendary Grand Hotel is located on historic Mackinac Island overlooking the Straits of Mackinac. Often called “America’s Summer Place,” this majestically colonnaded National Historic Landmark is open seasonally from early May through October. Vacations at the Grand Hotel are beloved family traditions, and generations have made priceless memories here. Mackinac Island is car-free, and families often enjoy taking carriage rides and hiking, cycling and horseback riding on Mackinac Island’s extensive network of trails.
The award-winning Grand Hotel features nearly 400 individually decorated rooms, 14 restaurants and bars, and an extensive array of attractions for all ages, including tennis, golf, tours and lectures, lawn games, carriage rides, the amenity-rich Woodlands Activity Center and the Esther Williams Swimming Pool. The luxury resort’s opulent public spaces, colorful gardens, and the longest porch in the world provide stunning backdrops for family group photos. The Grand Hotel’s American Plan rates include three meals daily and resort amenities.
The Hotel Hershey, Pennsylvania
Multi-generational groups can look forward to a wide variety of sweet experiences at The Hotel Hershey. Families have been vacationing at this Forbes Four-Star, AAA Four Diamond landmark in “Chocolate Town USA” since 1933. As one of Hersheypark’s official resorts, The Hotel Hershey provides guests with free resort benefits, including the best pricing on Hersheypark amusement park tickets, extended park hours and free admission to other Hershey attractions.
Family groups can choose from 326 spacious rooms and suites, including the Villas at The Hotel Hershey. The historic luxury hotel features multiple full-service restaurants, an outdoor aquatic complex and indoor pool, an 18-hole putting course, an outdoor recreation complex, and a 40,000-square-foot spa. Families can enjoy a wide range of indoor and outdoor games and activities, including Hershey Character Appearances, chocolate bingo, falconry, Adventure Explorations, and access to award-winning golf courses.
Mohonk Mountain House, New York
Multi-generational families will enjoy celebrating together at this stunning cliff-top Victorian castle located just 90 miles from New York City. Set in the Shawangunk Mountains, Mohonk Mountain House has been family-owned and operated since 1869. Family groups can select from an array of elegant accommodations, including 262 rooms and suites, and the six-bedroom Grove Lodge.
All-inclusive vacations at Mohonk Mountain House feature three meals daily, most non-alcoholic beverages, afternoon tea, and many activities. These include lake and indoor swimming, boating, fishing, hiking on over 85 miles of trails, golf, tennis, wellness sessions, family programs and nightly entertainment. Treatments at the world-class Spa at Mohonk Mountain House are offered for an additional charge. The National Historic Landmark also offers fun-filled winter outdoor adventures, such as snow tubing, ice skating and cross-country skiing. A Junior Naturalist program and year-round Kids’ Club programs are also available.
Hotel del Coronado, California
Oceanfront resorts are often a sought-after choice for memorable multi-generational family trips and celebrations. The award-winning Hotel del Coronado has catered to vacationing families and multi-generational groups for over 135 years. Set on one of America’s most beautiful beaches, the historic Hotel del Coronado has completed a more than $550 million six-year revitalization project. Guests can choose from luxurious accommodations in The Del’s five distinct neighborhoods, including beachfront options. Multi-bedroom seaside cottages and villas are also available.
While this National Historic Landmark is an architectural masterpiece, families often flock to the Hotel del Coronado for its fabulous oceanfront setting and numerous attractions. The resort features an array of year-round and seasonal activities, including swimming, biking, surfing, roller skating, movies on the beach, and private beach bonfires with unlimited s’mores. The Del’s Ocean Explorers and Explorers Night Out children’s programs for ages 5-10 are also offered.
The Omni Homestead Resort, Virginia
Known as America’s first resort, The Omni Homestead Resort has long been a much-loved choice for luxury multi-generational vacations. Encompassing over 2,300 acres in Virginia’s Allegheny Mountains, the historic property has been welcoming vacationers and 23 U.S. presidents for over 250 years. Fresh from a recently completed $170 million renovation, The Omni Homestead Resort caters to multi-generational groups with 483 luxurious rooms and suites, multiple dining venues, and a wealth of amenities.
Family members of all ages can enjoy more than 40 indoor and outdoor amenities at this elegant four-season resort. Attractions include championship golf, tennis, horseback riding, sporting clays, a 60,000-square-foot spa, the Warm Springs Pools, fly fishing, falconry, zip lining, movies in the theater, and fun at the resort’s two-acre water park. Skiing, snowboarding and ice skating are available in the winter months. The Homestead’s Adventure Kids and Adventure @ Night programs are offered for children aged 5-10.
Mirror Lake Inn Resort & Spa, New York
Luxury, timeless beauty and family-friendly charm combine perfectly at Upstate New York’s Mirror Lake Inn Resort & Spa. The family-owned and operated AAA Four Diamond resort has been welcoming family groups for over 100 years. The elegant property is also a member of Small Luxury Hotels of the World. Multi-generational families can choose from spacious rooms and suites, including some multi-bedroom suites with private balconies and lakeside views. The resort’s award-winning restaurants are ideal for celebratory events, and service is exceptional.
Mirror Lake Inn provides an authentic Adirondack experience for vacationing family groups throughout the year. During the summer months, guests can enjoy the eight-acre resort’s private beach and a variety of complimentary watersports, as well as hiking, golf, tennis, fishing, yoga classes and swimming in the outdoor heated pool. Nearby winter options are plentiful, including ice skating and skiing. Lake Placid’s Olympic Center and 1980 Olympic venues are available throughout the year.
By Nancy Schretter, Contributing Editor
Header Photo Credit: Hershey Entertainment & Resorts