5 Great Travel Deals for Fall

Save money on a trip to the Eastern Shore, New York, the Caribbean, Nashville, or Boston.

Get a third night free at the Chesapeake Hyatt resort on Maryland's Eastern Shore. Photo courtesy of Hyatt.

Autumn on the Eastern Shore 

Where: Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, Cambridge, Md.; 410-901-1234.

What’s special: In the fall, the waterfront Hyatt Regency Chesapeake Bay resort offers hayrides to view fall foliage; birding opportunities at its 18-acre wildlife refuge, Blue Heron Rookery; and food and cocktails that reflect the season. Guests can also tee off at River Marsh Golf Course, and lounge by the heated indoor pool. The recently reopened Blue Point Provision, a waterfront eatery, offers views of the Choptank River. And new this year is “The Cove,” a virtual golf simulator that provides an extensive library of courses golfers can play, as well as augmented reality analysis and golf lessons. Guests can also work out at the fitness center, relax at the spa, and, in the evening, make s’mores by an outdoor fire. Off-property there are pumpkin patches to visit and the restaurants and shops of nearby St. Michaels.

The deal: The “Fall on Sale” package gives guests every third night free and a $30 food and beverage credit per stay. In addition, Washingtonian readers who show this deal at check-in receive a free s’mores kit. Room rates start at $309.

When: Book by November 20 for stays through November 30.

Nonstop to the Caribbean 

Where: The Somerset on Grace Bay, Providenciales, Turks and Caicos Islands; 888-386-8770.

What’s special: Set on a magnificent Turks and Caicos white-sand beach and surrounded by crystal turquoise waters, this luxury resort has just 53 one- to five-bedroom accommodations, each with living, dining, and entertainment spaces plus gourmet kitchens and washer/dryer. The intimate resort has two restaurants and bars, two freshwater pools, a fitness center, and a full-service spa with in-room services. Guests can paddleboard or kayak on site, and the concierge can arrange kiteboarding, deep-sea fishing, snorkeling, scuba diving, parasailing, horseback riding, or an ocean-side culinary experience.

The deal: The deal includes a welcome drink; complimentary breakfast daily; Monday evening managers’ cocktail hour with appetizers; non-motorized watersports; a kids camp (two sessions daily, Monday through Saturday); and free wi-fi throughout the property. Washingtonian readers also get a complimentary sunset cruise with bubbly for two (normally $124 a person). One-bedroom townhomes with a balcony terrace (sleeps two adults and two children) start at $700 a night. To book, click here. There are nonstop flights from Dulles via United.

When: Valid for stays October 9 through December 19.

Fall in New York

Where: InterContinental New York Times Square, 300 W. 44th St., New York; 212-803-4500.

What’s special: All the rooms at this hotel average 350 square feet, and floor-to-ceiling windows provide views of the Manhattan skyline and Hudson River. On-site is a 24-hour-access fitness center, as well as Stinger Cocktail Bar and Kitchen serving craft cocktails and all-day dining—beehives on the rooftop produce the honey used in their cocktails. The hotel is steps from Times Square and Broadway theaters, and close to Central Park and Rockefeller Center. Room rates start at $199.

The deal: The “Washingtonian Exclusive” deal gives readers a $25 food and beverage credit when using this link to book. Room rates start at $199 a night.

When: Valid for stays through February 29, 2024.

Rowing on the Charles River

Where: Hotel Commonwealth, Boston; 617-933-5000.

What’s special: The hotel is centrally located—next to a T station, steps from Fenway Park, and close to Boston and Northeastern universities, Back Bay, and the North End. There’s coffee and tea in the lobby. One of the largest rowing regattas in the world, the Head of the Charles, returns to Boston October 20 through 22—just as fall foliage colors begin to peak along the river. More than 11,000 rowers from around the globe will compete. Through a new partnership with nonprofit Community Rowing, guests of the hotel can get a taste of the sport through private indoor instruction, followed by an on-water experience with one of Community Rowing’s coaches.

The deal: The “Rowing on the Charles River” package includes overnight accommodations; a personalized rowing experience on the Charles River from Community Rowing; and a healthy gift basket upon arrival, featuring protein bars and nuts. Washingtonian readers also receive a free bottle of wine. The package starts at $1,529.00 for two. Washingtonian readers also receive 20 percent off the room rate if staying another night. Room rates start at $499. To book, call 617-532-5019 and mention the Washingtonian deal.

When: Valid for stays through November.

Vintage Hotel in Music Town

Where: The Hermitage Hotel, Nashville; 615-244-4121.

What’s special: Located in the heart of downtown Nashville, the hotel opened in 1910 and is a National Historic Landmark. In 2022 the luxury hotel completed a multi-year revitalization of its rooms, suites, and public spaces, as well as restoration of its Beaux Arts architecture. The hotel is home to two new restaurants from Michelin-starred chef Jean-Georges Vongericthen—Drusie & Darr and the Pink Hermit. There’s also a 24-hour gym. The original painted-glass ceiling is still the centerpiece of the magnificent lobby, while the colors of rugs and walls are a more serene color palette. Another famous spot is the 1930’s lower-level men’s restroom with its Art Deco green-and-black tile and a retro shoeshine set-up. Not to be outdone, during the renovation a lavish ladies’ room with striped walls, floors of variegated pink marble, arched doorways, and pink fixtures was designed. The guest rooms still retain their crown molding and marble bathrooms but have been modernized with in-mirror televisions, Frette linens, and plush robes. The hotel is across the street from the Tennessee Performing Arts Center and near many restaurants. Other attractions include the Grand Ole Opry House and brewery and distillery tours.

The deal: The “Dine and Unwind” package includes a $100 per night dining credit valid for lunch or dinner at Druise & Darr by Jean-Georges. Washingtonian readers also receive two complimentary cocktails and a room upgrade based on availability. Room rates start at $449 a night. To book call 615-244-3121 and mention the Washingtonian deal.

When: Valid for stays through March 2024.