Holiday travel · September 7, 2026
Top 20 Hotel Destinations for Labor Day
Make the most of the last long weekend of summer, from the Telluride Film Festival to warm-water beach towns and the first harvest in wine country.
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Colorado, United States
Why Labor Day
The Telluride Film Festival takes place over Labor Day weekend.
- Typical weather
- Highs ~72°F (22°C); crisp
- Crowds · season
- High · Peak
- Price level
- $$$$
- adventure
- culture
Where we'd stay: The Madeline Hotel & Residences, Auberge Resorts Collection. Mountain Village hotel with gondola access to town.
Explore Telluride →Wauwinet, Massachusetts, United States
Why Labor Day
The last big summer weekend on Nantucket, with warm water.
- Typical weather
- Highs ~72°F (22°C); pleasant
- Crowds · season
- Low · Shoulder
- Price level
- $$$$
- beach
- romance
Where we'd stay: White Elephant Hotel. A five-star stay in Nantucket, a strong base for Nantucket.
Hotels in Massachusetts →New York, United States
Why Labor Day
Montauk's final summer weekend, with warm water and fewer crowds afterward.
- Typical weather
- Highs ~75°F (24°C); warm
- Crowds · season
- High · Peak
- Price level
- $$$$
- beach
Where we'd stay: Gurney's Montauk Resort & Seawater Spa. Oceanfront resort with a seawater spa.
Hotels in Montauk →Edgartown, Massachusetts, United States
Why Labor Day
An end-of-summer weekend on Martha's Vineyard.
- Typical weather
- Highs ~75°F (24°C); warm
- Crowds · season
- High · Peak
- Price level
- $$$$
- beach
- family
Where we'd stay: Harbor View Hotel. Historic hotel overlooking Edgartown Lighthouse.
Hotels in Edgartown →Maine, United States
Why Labor Day
The late-summer coast, with fall foliage just weeks away.
- Typical weather
- Highs ~72°F (22°C); mild
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$$
- beach
- romance
- family
Where we'd stay: White Barn Inn, Auberge Resorts Collection. Classic New England inn known for its candlelit restaurant.
Hotels in Kennebunkport →
Stateline, Nevada, United States
Why Labor Day
Warm, dry Lake Tahoe days, with fewer crowds after the holiday.
- Typical weather
- Highs ~77°F (25°C); dry
- Crowds · season
- High · Peak
- Price level
- $$$$
- beach
- adventure
- family
Where we'd stay: Edgewood Tahoe Resort. Lakefront lodge on a championship golf course.
Explore Lake Tahoe →Forestville, California, United States
Why Labor Day
Harvest season begins in Sonoma.
- Typical weather
- Highs ~84°F (29°C); dry
- Crowds · season
- High · Peak
- Price level
- $$$$
- culture
- romance
Where we'd stay: Farmhouse Inn. Russian River Valley inn known for its restaurant and spa.
Hotels in Forestville →
Montecito, California, United States
Why Labor Day
Warm weather returns to Santa Barbara as summer fog fades.
- Typical weather
- Highs ~76°F (24°C); sunny
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$$
- beach
- romance
Where we'd stay: Rosewood Miramar Beach. Beachfront estate in Montecito.
Explore Santa Barbara →
California, United States
Why Labor Day
San Francisco's warmest stretch of the year begins in September.
- Typical weather
- Highs ~70°F (21°C); sunny
- Crowds · season
- Moderate · Peak
- Price level
- $$$$
- city
- culture
Where we'd stay: Four Seasons Hotel San Francisco at Embarcadero. High-floor rooms with bay and skyline views in the Financial District.
Explore San Francisco →
10Seattle
Washington, United States
Why Labor Day
Bumbershoot, Seattle's long-running music and arts festival, is usually held over Labor Day weekend.
- Typical weather
- Highs ~73°F (23°C); dry
- Crowds · season
- High · Peak
- Price level
- $$$
- city
- nature
Where we'd stay: Four Seasons Hotel Seattle. Waterfront hotel near Pike Place Market with an infinity pool.
Explore Seattle →Jackson, Wyoming, United States
Why Labor Day
Early fall color and fewer crowds around Grand Teton.
- Typical weather
- Highs ~68°F (20°C); crisp
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$$
- nature
- adventure
Where we'd stay: Hotel Yellowstone at Jackson Hole. A five-star stay in Jackson, a strong base for Grand Teton.
Hotels in Jackson →Avon, Colorado, United States
Why Labor Day
Mountain biking and the first hints of fall color.
- Typical weather
- Highs ~68°F (20°C); crisp
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$
- nature
- family
Where we'd stay: Park Hyatt Beaver Creek Resort and Spa, Vail Valley. A five-star stay in Beaver Creek, a strong base for Beaver Creek.
Hotels in Colorado →
Michigan, United States
Why Labor Day
The annual Mackinac Bridge Walk is held on Labor Day morning.
- Typical weather
- Highs ~70°F (21°C); mild
- Crowds · season
- High · Peak
- Price level
- $$$
- family
- culture
Where we'd stay: The Inn at Stonecliffe. A five-star stay in Mackinac Island, a strong base for Mackinac Island.
Explore Mackinac Island →
14Chicago
Illinois, United States
Why Labor Day
The Chicago Jazz Festival is usually held over Labor Day weekend in Millennium Park.
- Typical weather
- Highs ~79°F (26°C); warm
- Crowds · season
- High · Peak
- Price level
- $$$
- city
- culture
- family
Where we'd stay: The Langham, Chicago. Riverfront hotel in a Mies van der Rohe-designed building.
Explore Chicago →Newberg, Oregon, United States
Why Labor Day
Harvest begins in the Willamette Valley.
- Typical weather
- Highs ~78°F (26°C); dry
- Crowds · season
- Moderate · Peak
- Price level
- $$$
- culture
- romance
Where we'd stay: The Allison Inn & Spa. Wine country inn surrounded by vineyards.
Hotels in Oregon →- 16
Big Sky
Montana, United States
Why Labor Day
Late-summer hiking and Yellowstone trips as crowds thin.
- Typical weather
- Highs ~72°F (22°C); dry
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$$
- adventure
- nature
- family
Where we'd stay: Montage Big Sky. Mountain resort with a bowling alley and Spa Montage.
Hotels in Big Sky → Whitefish, Montana, United States
Why Labor Day
Going-to-the-Sun Road is still open for late-summer hiking.
- Typical weather
- Highs ~72°F (22°C); dry
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$
- nature
- adventure
Where we'd stay: The Lodge at Whitefish Lake. Lakeside lodge with a marina, about 30 minutes from the park.
Hotels in Whitefish →Lake Placid, New York, United States
Why Labor Day
Late-summer paddling and hikes in the Adirondacks.
- Typical weather
- Highs ~72°F (22°C); mild
- Crowds · season
- Moderate · Shoulder
- Price level
- $$$
- nature
- adventure
- family
Where we'd stay: Whiteface Lodge. Rustic-luxe lodge with an indoor-outdoor pool.
Hotels in Lake Placid →- 19
Newport
Rhode Island, United States
Why Labor Day
Newport's last summer weekend before the quieter fall season.
- Typical weather
- Highs ~75°F (24°C); warm
- Crowds · season
- High · Peak
- Price level
- $$$$
- beach
- culture
Where we'd stay: The Chanler at Cliff Walk. Oceanfront mansion hotel at the start of the Cliff Walk.
Hotels in Newport → 
20Cape Cod
Chatham, Massachusetts, United States
Why Labor Day
Warm water at the end of Cape Cod's summer season.
- Typical weather
- Highs ~75°F (24°C); warm
- Crowds · season
- High · Peak
- Price level
- $$$$
- beach
- family
Where we'd stay: Chatham Bars Inn. Waterfront inn with a private beach and its own farm.
Explore Cape Cod →