Best Trips for Grandparents and Grandkids: 11 Luxe Escapes

By Andrea Caughey
September 17, 2025
8 Min Read

Planning a vacation with your grandchildren may sound daunting, but choose the right destination and it morphs into something spectacular all around. Today’s grandparents don’t have to choose between traveling with the younger set and enjoying luxury accommodations, as acclaimed hotels and resorts across the U.S. cater to all ages and many make families a priority. The best part? Trading logistical stress for turnkey fun. Here are 11 U.S. lodging gems that check grandkids’ and grandparents’ boxes alike.

A large, multi-story brick building with colonial-style architecture features dormer windows, a prominent chimney, and an expansive screened porch spanning the ground level with wide stone steps leading up to it. The building is surrounded by manicured lawns and mature landscaping, including palm trees and a large oak draped with Spanish moss. In the foreground, there is a circular stone fire pit area on the grass lawn under a partly cloudy blue sky. — Photo courtesy of Montage Hotels & Resorts

11 of the Best Trips for Grandparents and Grandkids

Montage Palmetto Bluff, Bluffton, SC

As a counterbalance to our mach-speed digital age, consider a slow-lane experience with your grand, surrounded by the best nature has to offer. Located in coastal Bluffton, South Carolina, amid 20,000 acres of Lowcountry beauty and wildlife, the Montage Palmetto Bluff allows kids outlets for riding bikes, fishing, kayaking, paddleboarding and more on miles of trails, paths and waterways. Two treehouses with hammocks, rope ladders and slides, plus grassy areas for lawn games, offer touches of nostalgia that will appeal to all ages. Several pools, casual restaurants and sea adventures like dolphin tours cater to families, while the fascinating, history-laden towns of Savannah and Charleston are an easy drive away.

Room pick: The resort’s freestanding Signature Residences each have between two and five bedrooms in addition to full kitchens, dining areas and screened-in porches (some with swings).

A luxury resort complex features a large rectangular swimming pool surrounded by lounge chairs and umbrellas, with modern southwestern-style buildings constructed in earthy terracotta tones. The property is set against a dramatic backdrop of towering red sandstone canyon walls and rock formations, with lush green trees providing contrast to the desert landscape. The scene is captured under a partly cloudy blue sky, showcasing the integration of contemporary architecture with the natural desert environment. — Photo courtesy of Enchantment Resort

Enchantment Resort, Sedona, AZ

Often thought of as a mini Grand Canyon due to its stunning red rock formations, Sedona is a paradise for outdoor enthusiasts. An epicenter for hiking trails and mountain bike circuits, the famed Enchantment Resort offers grandparents and their charges luxury adobe-style lodging, some in casitas with patios and fireplaces. Curated nature treks, art workshops (pottery, beading and more), pickleball and tennis, stargazing and even axe-throwing are a few of the options. Adventure seekers can dive into backcountry hikes and climbs, iconic “Pink Jeep” countryside tours and hot air balloon rides.

Room pick: One- and two-bedroom suites across several categories can sleep anywhere from four to 10 people, with configurations that include fold-up Murphy beds for maximum use of space. All include private decks or patios as well as fireplaces, and some have kitchenettes, outdoor grills and/or private plunge pools.

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Cliff House Maine, Cape Neddick, ME

Crowning the craggy and wild Maine coastline, Cliff House Maine is both elegant and casual. Children are an important focus, with a dedicated kids’ pool, arts and crafts program, digital scavenger hunts, lawn sports and two movies shown daily in a mini theater. Only an hour north of Boston and a guest trolley ride away from Ogunquit, the resort also offers 70 acres of shoreline for hiking, tidepooling and kayaking. Winter months welcome snowshoeing, nearby cross country skiing, blazing bonfires, lighthouse tours and more.

Room pick: Sleepaway Bunk Suites come with a king bed for grandparents plus bunk beds and a sleeper sofa for younger ones, along with a private balcony overlooking the crashing waves.

An aerial view shows a large Victorian-style resort hotel with distinctive red tile roofs and white walls, featuring a prominent conical tower topped with a cupola and American flag. The grand multi-story building sits directly on a sandy beach with the Pacific Ocean beyond, surrounded by palm trees and manicured grounds that include what appears to be a swimming pool area. The coastline curves along the horizon under a clear blue sky, with distant hills visible across the water. — Photo courtesy of Hotel del Coronado

Hotel del Coronado, Coronado, CA

Dating back more than a century on San Diego’s iconic Coronado Island and fresh from a top-to-tail renovation, the “Hotel Del” offers historic charm in a coveted beachside locale. For the full SoCal experience, grandkids can take surf lessons; learn to sail; enjoy boogie boarding, kayaking and virtual reality snorkeling; huddle around beach bonfires; and explore countless tidepools and shelling spots. A quick drive over the Coronado bridge takes you to the highlights of San Diego: the Zoo, Balboa Park, Sea World, Legoland and more.

Room pick: Two- and three-bedroom villas not only offer ample sleeping space, but feature fireplaces, full kitchens and dining areas, washer/dryers and fireplaces.

A luxury mountain resort features a large outdoor swimming pool and hot tub surrounded by lounge chairs and outdoor dining furniture on a stone patio. The resort buildings showcase a mix of architectural styles including stone, wood siding, and traditional alpine design elements, set against a backdrop of snow-capped mountains and green foothills. Multiple levels of accommodations and terraced outdoor spaces create an upscale mountain village atmosphere. — Photo courtesy of Auberge Resorts Collection

Madeline Hotel and Residences, Telluride, CO

The glorious mountains of Colorado, especially magical Telluride, offer grands a healthy mix of scenic beauty and rugged pursuits. In summer, easy access to the gondola and trails accommodates hiking, bouldering, fly-fishing and mountain climbing, while winters delight skiers, snowboarders, sledders and ice skaters on the rink just outside. The Madeline includes a kids’ hangout room (20 Below), an outdoor pool and hot tub, daily alphorn performances and a Dylan’s Candy Bar outpost.

Room pick: The Madeline’s two- to four-bedroom residences come equipped with sleeper sofas, full kitchens, washer/dryers and village or mountain views.

A large beachfront resort hotel with distinctive twin towers topped by red tile roofs sits on a white sandy beach surrounded by palm trees and tropical vegetation. In the foreground, a white catamaran sailboat floats in clear turquoise waters under a blue sky. The multi-story building features Mediterranean or Spanish colonial-style architecture and extends along the coastline. — Photo courtesy of The Ritz-Carlton, Naples

The Ritz-Carlton Naples, Naples, FL

Beachcombing is at its best on this Ritz-Carlton property on a luxurious three-mile stretch of pristine Gulf sand in Naples. Families have always been a priority with the iconic luxury hotel brand, including its signature Ritz Kids program for ages 5 to 12. Browse for shells, take arts and crafts classes or try your hand at beach games. Adrenaline junkies can indulge in parasailing, wave runners, body and skim boards and offshore fishing. Trips to the Everglades and sites in Naples, such as the zoo, are close by.

Room pick: Choose a one- to three-bedroom oceanfront or oceanview suite for maximum space to spread out plus prime vistas over the water.

An aerial view shows a sprawling resort complex with white Mediterranean-style buildings featuring red tile roofs, scattered across rolling hills and connected by winding pathways. The property includes a prominent golf course with manicured green fairways in the foreground, along with what appears to be a central pool and recreation area surrounded by guest accommodations. The entire resort is set against a dramatic backdrop of rugged mountains under a clear blue sky, with dense vegetation and mature trees interspersed throughout the grounds. — Photo courtesy of Ojai Valley Inn & Spa

Ojai Valley Inn & Spa, Ojai, CA

Northwest of Los Angeles and east of Santa Barbara, the small town of Ojai is often dubbed “Shangri-La” for its scenic foothill setting and spiritual past. Meandering across 220 acres, the Mediterranean complex of Ojai Valley Inn & Spa feels a world apart. Among abundant family-friendly amenities, the resort offers a kid-centric “Pixie Pool,” bike rentals, evening s’mores, seasonal “dive-in” movies, picnic baskets, art lessons and camps. It’s just a few minutes’ drive from Ojai’s walkable downtown as well.

Room pick: The inn’s Fontana Suites have a king bedroom plus separate living area with a sleeper sofa, and two balcony patios from which to enjoy the surrounding mountain views.

A group of people in casual summer clothing walks along a sandy path bordered by beach grass, with a young person in a white t-shirt and blue shorts leading the group. Behind them stand large white Mediterranean-style buildings with red tile roofs, arched windows, and palm trees, suggesting a luxury beachfront resort or residential development. The scene is set under a clear blue sky with natural dune vegetation framing the walkway. — Photo courtesy of Sea Island Resort

The Cloister at Sea Island, Sea Island, GA

Bathed in a magical glow from morning ‘til night, the Golden Isles along the coast of Georgia offer a temperate climate year-round. The centerpiece of them all is the iconic Cloister at Sea Island, a beloved gathering spot for generations of families. Be sure to hit the Beach Club, with its family pools, ice cream/candy shop, casual dining, 100-seat movie theater and game rooms. Surrounded by a wealth of marine and plant life, the Sea Island Nature Center offers meet-and-greets with indigenous animals, guided treks through marshes and forests and the opportunity to be a Junior Turtle Technician. Paddleboarding and kayaking, surf lessons, horseback riding and biking add to the open-air fun.

Room pick: Two-bedroom Wing Suites have one sleeping space with a king bed and one with two queens, plus a sleeper sofa; other amenities include fireplaces, patios and balconies.

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A classic wooden motorboat with passengers cruises across a lake, creating a wake as it moves through the dark blue water. In the background, a large multi-story lodge or mansion with dark wood construction and multiple gabled rooflines sits on a manicured lawn that slopes down to the shoreline. The property features several boat docks along the water's edge and is surrounded by dense forest, with red umbrellas or seating areas visible on the green lawn. — Photo courtesy of Lake Placid Lodge

Lake Placid Lodge, Lake Placid, NY

While Lake Placid Lodge is more tailored to older kids than younger ones, tween and teen grands will revel in the variety of seasonal sports and nature adventures there. Poised along one of the Adirondacks’ most spectacular and storied lakes, the lodge’s cabins and cottages give families lots of room to spread out. Most have fireplaces and porches for alfresco meals. Don’t miss canoeing, fishing and hiking amid the nearby trails and waterfalls, or wintertime ice skating, cross-country skiing and snow sports.

Room pick: Although the lodge’s two-bedroom cabins include comfortable living areas and wood-burning fireplaces, the best feature is the private deck with a retractable awning to guard against sudden shifts in the weather.

An aerial view shows a collection of traditional shingled houses positioned along a curved coastline, with manicured green lawns extending toward sandy beaches and a protected harbor. The calm blue waters are dotted with numerous sailboats and small vessels at anchor, while low-lying islands and tidal marshlands are visible in the distance. The coastal community appears nestled between the water and inland vegetation under a partly cloudy sky. — Photo courtesy of Chatham Bars Inn

Chatham Bars Inn, Chatham, MA

The heartbeat of Cape Cod, the village of Chatham is a great jumping-off point for the rest of the region’s small towns, parks and beaches. It also has its share of boutiques and ice cream parlors, plus a minor league baseball team and a bandshell for summer concerts. The idyllic Chatham Bars Inn offers grandparents and grandkids the perfect launching pad for all of this, plus swimming and beachcombing, whale watching, lobstering, biking, clambakes and other summer pleasures.

Room pick: Ocean View Suites in the Main Inn combine a king bedroom with a living room that’s outfitted with a pullout sleeper sofa, plus a deck or balcony and, in some cases, a fireplace.

A cityscape photograph taken during dusk shows a mix of modern high-rise buildings and classical architecture along a busy urban street. The scene captures illuminated building windows against a blue twilight sky, with light trails from moving vehicles creating streaks on the street below. Traffic lights, street lamps, and the warm glow from building interiors create a vibrant evening atmosphere in this metropolitan setting. — Photo courtesy of The Peninsula Chicago

The Peninsula Chicago, Chicago, IL

Chicago is a delight for all generations, with legendary museums like the Griffin Museum of Science and Industry, the Art Institute of Chicago, the Field Museum of Natural History and Shedd Aquarium, to name a few. Expansive Grant Park along Lake Michigan accommodates biking, strolling, sailing and cavorting at Navy Pier. Nearby, along the popular Magnificent Mile, The Peninsula Chicago welcomes kids at every turn, including its popular Camp Peninsula program with in-room tent, plentiful board games and a visit by Pen Bear. Digital scavenger hunts and youth-slanted spa and fitness classes such as ballet and water aerobics combine with city experiences ranging from the Lincoln Park Zoo to urban kayaking.

Room pick: As with many urban hotels, your best bet is to book connecting guest rooms to provide grandkids a little privacy yet remain close at hand. Opt for the Deluxe Rooms, which offer spectacular views of the Chicago skyline.

Relevant Links:

Browse all tips and ideas for multigenerational family travel on Ciao Bambino

How to nail travel with grandchildren: Our insider guide

How to plan a multigenerational family vacation everyone will love

5 tips to make multigenerational travel fun for all

Best U.S. hotels and resorts for a multigenerational family vacation

Best tips for a multigenerational family trip to Europe

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.

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Best Trips for Grandparents and Grandkids: 11 Luxe Escapes