Travelers' Field Guide logo

Attraction: Places to Stay

  • The Roxbury Motel – Roxbury, NY

    The Roxbury Motel – Roxbury, NY

    The Roxbury Motel

    Roxbury, NY

    the-roxbury-motel-roxbury-ny
    The Roxbury Motel’s theatrical exterior sets the stage long before you step inside. 📸 The Roxbury Motel

    The Roxbury Motel
    • Address: 2258 County Hwy 41, Roxbury, NY 12474
    • State: New York
    • Website: theroxburyexperience.com

    Overview
    The Roxbury Motel is a Catskills landmark known for its theatrical design, storybook architecture, and commitment to doing things differently. From the exterior alone, it’s clear this is not a traditional roadside stay.

    Why It’s Worth a Stop
    It’s memorable in the best way. The Roxbury leans fully into whimsy and creativity, making it a standout for travelers who appreciate humor, bold visuals, and a sense of play baked into their surroundings.

    What to Know Before You Go
    • Every room is uniquely themed
    • Advance booking is strongly recommended
    • Located in the Catskills, about a scenic drive from NYC
    • Best suited for adults or older teens

    Fun Fact
    Many guests return specifically to stay in a different themed room each time.

  • 20 South Battery – Charleston, SC

    20 South Battery – Charleston, SC

    20 South Battery

    Charleston, SC

    20-south-battery-charleston-sc
    A horse-drawn carriage passes in front of 20 South Battery, a familiar scene along Charleston’s historic Battery. 📸 20 South Battery

    20 South Battery
    • Address: 20 S Battery St, Charleston, SC 29401
    • State: South Carolina
    • Website: https://20southbattery.com/

    Overview

    Set directly across from White Point Gardens, 20 South Battery is one of Charleston’s most storied historic estates. Dating to the 1800s and meticulously restored beginning in 2018, the property invites guests to stay within a landmark rather than simply admire it from the street. Covered piazzas, quiet gardens, and harbor views lend the estate a distinctly residential presence along the Battery.

    Why It’s Worth a Stop

    This is Charleston at its most atmospheric and unhurried. Mornings unfold on the porch with views of the water, afternoons drift through shaded gardens and historic rooms, and evenings are made for long walks along the Battery promenade. With a limited number of rooms and an emphasis on calm, 20 South Battery is ideal for travelers who value history, privacy, and a strong sense of place.

    What to Know Before You Go

    • Adult-oriented property with a small number of individually designed rooms and suites
    • Two distinct stay experiences: the historic Mansion or the quieter Carriage House and Courtyard Rooms
    • Breakfast included
    • Fourth-floor library with sweeping views of the harbor and Charleston skyline
    • Walkable to waterfront paths, historic homes, and downtown Charleston

    Fun Fact

    The estate underwent a two-year, research-driven restoration to return it to its Gilded Age character. A dedicated history book documents the property’s layered past and the lives once lived within its walls.

  • The Inn at Willow Grove – Orange, VA

    The Inn at Willow Grove – Orange, VA

    The Inn at Willow Grove

    Orange, VA

    the-inn-at-willow-grove-orange-va
    The Inn at Willow Grove rests among rolling fields and historic countryside in central Virginia. 📸 The Inn at Willow Grove

    The Inn at Willow Grove
    • Address: 14079 Stones Throw Dr, Orange, VA 22960
    • State: Virginia
    • Website: https://innatwillowgrove.com

    Overview

    Tucked into the rolling foothills of central Virginia, The Inn at Willow Grove is a refined country retreat set on a historic 40-acre estate. With a lovingly restored 18th-century manor house and a collection of thoughtfully designed cottages, the Inn blends polished comfort with a sense of ease that feels genuinely welcoming.

    Why It’s Worth a Stop

    Luxury here is quiet and unforced. Days unfold around long breakfasts, spa appointments, and unhurried meals at the Inn’s restaurant and pub, with little reason to leave the property once you arrive. It’s ideal for travelers who appreciate beautiful surroundings, attentive service, and a pace that encourages staying put.

    What to Know Before You Go

    • Boutique property with 25 individually designed rooms and suites
    • Full-service spa on site, popular with both guests and locals
    • On-site restaurant and pub featuring seasonal, locally sourced menus
    • Best suited for adults seeking a calm, restorative stay
    • Advance reservations recommended, especially on weekends

    Fun Fact

    The main manor dates to the late 1700s, and today pairs its historic bones with modern design, original art, and no two rooms alike.

  • Red Lion Inn – Stockbridge, MA

    Red Lion Inn – Stockbridge, MA

    Red Lion Inn

    Stockbridge, MA

    red-lion-inn-stockbridge-ma
    Fall settles in around The Red Lion Inn, a longtime gathering place at the center of Stockbridge. 📸 Red Lion Inn

    Red Lion Inn
    • Address: 30 Main St, Stockbridge, MA 01262
    • State: Massachusetts
    • Website: https://redlioninn.com

    Overview

    With more than two centuries of history behind it, The Red Lion Inn has long been a gathering place in the Berkshires. Its layered rooms, antique-filled hallways, and creaking staircases speak to the past, while porches, courtyards, and shared spaces keep the Inn rooted firmly in the present.

    Why It’s Worth a Stop

    Life at the Inn unfolds at many speeds. Mornings might start quietly on the front porch, afternoons drift by at the heated pool or exploring Stockbridge, and evenings bring courtyard dinners, live music, or a stop in the speakeasy. It’s a place that welcomes both restoration and celebration, often under the same roof.

    What to Know Before You Go

    • Four distinct lodging experiences, including the Main Inn, Maple Glen, and Village Houses
    • No two rooms are alike; layouts and styles vary by building
    • On-site dining, courtyard seating, and a prohibition-era speakeasy with live music
    • Year-round heated pool and hot tub; spa partners nearby
    • Very popular during fall foliage season
    • Some rooms require stairs; accessibility varies

    Fun Fact

    Norman Rockwell lived nearby and often drew inspiration from Stockbridge’s streets and community life, much of which still centers around the Inn.

  • Driftwood Motel – Montauk, NY

    Driftwood Motel – Montauk, NY

    Driftwood Motel

    Montauk, NY

    driftwood-motel-montauk-ny
    Light-filled interiors at the Driftwood Motel reflect Montauk’s easy, ocean-first pace. 📸 Driftwood Motel

    Driftwood Motel
    • Address: 2178 Montauk Hwy, Montauk, NY 11954
    • State: New York
    • Website: https://www.driftwoodmontauk.com/

    Overview

    Set on a low bluff above the Atlantic, the Driftwood Motel is an old-school Montauk stay with front-row ocean views and wide, open grounds. It feels relaxed and unpolished in the best way, shaped more by salt air and sunsets than trends.

    Why It’s Worth a Stop

    This is Montauk before the scene. Fire pits flicker at dusk, Adirondack chairs face the water, and days revolve around the beach rather than reservations. It’s especially appealing outside peak summer, when the coastline quiets down and the ocean takes center stage.

    What to Know Before You Go

    • Seasonal property, typically open late spring through early fall
    • Mix of oceanfront and oceanview rooms, plus cottages
    • Direct beach access, pool, and outdoor gathering spaces
    • Not walkable to town; a car is helpful
    • Many activities and events are offered in the peak summer months

    Fun Fact

    Montauk has long been called “The End,” a nickname that still fits when you’re watching the sun drop into the Atlantic from the Driftwood’s bluff.

  • Hunting Island State Park Campground – Hunting Island, SC

    Hunting Island State Park Campground – Hunting Island, SC

    Hunting Island State Park Campground

    Hunting Island, SC

    hunting-island-state-park-campground-hunting-island-sc
    A quick selfie with a park ranger, whose days are spent guiding visitors, monitoring wildlife, and keeping the park running smoothly. 📸 Hunting Island State Park

    Hunting Island State Park Campground
    • Address: 2555 Sea Island Pkwy, Hunting Island, SC 29920
    • State: South Carolina
    • Website: southcarolinaparks.com/hunting-island

    Overview

    Hunting Island State Park Campground sits among maritime forest and sandy shoreline, offering one of the most scenic camping experiences on the South Carolina coast.

    Why It’s Worth a Stop

    You can camp beneath palmettos, walk straight to the beach, and climb a historic lighthouse all in one day. (*The Hunting Island Lighthouse is currently closed for repairs.  The lighthouse can still be viewed from the grounds, and docents are on hand to interpret and give more information about the lighthouse.)

    What to Know Before You Go

    • Sites for tents and RVs
    • Beachfront and forest sites available
    • Mosquito repellent recommended
    • Wildlife sightings are common, from shorebirds along the beach to deer in the forest

    Fun Fact

    Hunting Island’s lighthouse was designed to be taken apart, which made it possible to move the entire structure inland when beach erosion threatened its original site in 1889.

  • Assateague Island National Seashore Campgrounds – Berlin, MD

    Assateague Island National Seashore Campgrounds – Berlin, MD

    Assateague Island National Seashore Campgrounds

    Berlin, MD

    assateague-island-national-seashore-campgrounds-berlin-md
    Wild ponies move quietly through the dunes near the campsites on Assateague Island. 📸 NPS

    Assateague Island National Seashore Campgrounds
    • Address: 7206 National Seashore Ln, Berlin, MD 21811
    • State: Maryland
    • Website: nps.gov/asis

    Overview

    Camping on Assateague Island puts you steps from the Atlantic, with dunes, wild ponies, and wide-open skies. Campsites range from bayside to oceanside, offering different views across the island.

    Why It’s Worth a Stop

    This is coastal camping at its most elemental. Salt air, wind, and the sound of waves shape the rhythm of each day.

    What to Know Before You Go

    • Reservations required and fill quickly (March 15 – November 15)
    • Expect wind and shifting sand
    • No electric hookups
    • Wild horses roam freely; food must be secured

    Fun Fact

    The famous ponies are believed to descend from horses that swam ashore after early shipwrecks.

  • Smugglers’ Notch State Park Campground – Stowe, VT

    Smugglers’ Notch State Park Campground – Stowe, VT

    Smugglers’ Notch State Park Campground

    Stowe, VT

    smugglers-notch-state-park-campground-stowe-vt
    A steady rush of water moves through Smugglers’ Notch, framed by mossy rock and shaded forest. 📸 Smugglers’ Notch

    Smugglers’ Notch State Park Campground
    • Address: 6443 Mountain Rd, Stowe, VT 05672
    • State: Vermont
    • Website: vtstateparks.com/smugglersnotch

    Overview

    Set at the base of Mount Mansfield, Smugglers’ Notch State Park Campground offers wooded campsites surrounded by steep cliffs and classic Green Mountain scenery. The park feels tucked away, even though it sits along one of Vermont’s most scenic drives.

    Why It’s Worth a Stop

    You wake up already on the trail. Hiking, scrambling through the Notch, and quiet mornings under the trees make this an ideal base for slow, outdoors-focused travel.

    What to Know Before You Go

    • Seasonal campground, typically open late spring through fall
    • The campground includes 20 tent sites and 14 lean-to sites
    • No hookups, but restrooms/showers and potable water available
    • Very popular during fall foliage season

    Fun Fact

    Long before the road was built, smugglers, traders, and later freedom seekers traveled this narrow pass on foot and horseback to move between Vermont and Canada.

  • Woodstock Inn & Resort – Woodstock, VT

    Woodstock Inn & Resort – Woodstock, VT

    Woodstock Inn & Resort

    Woodstock, VT

    woodstock-inn-and-resort-woodstock-vt
    The Woodstock Inn & Resort, facing the village green, where arrivals feel easy and lingering feels natural. 📸 Woodstock Inn & Resort

    Woodstock Inn & Resort
    • Address: 14 The Green, Woodstock, VT 05091
    • State: Vermont
    • Website: woodstockinn.com

    Overview
    Anchoring Woodstock’s village green, the Woodstock Inn & Resort blends New England heritage with understated luxury. Fireplaces glow in nearly every common room, and the on-site Red Rooster restaurant serves seasonal Vermont dishes that taste like the countryside around them.

    Why It’s Worth a Stop
    It’s the town’s centerpiece during Wassail Weekend — warm, festive, and quietly elegant. The inn captures everything visitors love about Vermont in winter: snow on the roofline, pine in the air, and breakfast by the fire.

    What to Know Before You Go

    • Open year-round; book early for December weekends.
    • On-site spa and a fitness club (nearby) available to guests.
    • Complimentary valet parking.
    • Located steps from the covered bridge and village shops.

    Fun Fact
    Laurance Rockefeller, who helped create America’s National Park System, founded the current resort in 1969 as a model of sustainable hospitality.

  • Congress Hall – Cape May, NJ

    Congress Hall – Cape May, NJ

    Congress Hall

    Cape May, NJ

    congress-hall-cape-may-nj
    Congress Hall’s iconic yellow exterior overlooking the beach in Cape May. 📸 Congress Hall

    Congress Hall
    • Address: 200 Congress Place, Cape May, NJ 08204
    • State: New Jersey
    • Website: congresshall.com

    Overview
    Known as America’s first seaside resort, Congress Hall has been welcoming guests since 1816. The sprawling yellow hotel sits just off the beach, glowing with holiday lights and history. Inside, the Blue Pig Tavern serves comfort food and coastal classics under wood beams and warm light.

    Why It’s Worth a Stop
    Congress Hall turns into Cape May’s centerpiece during the holidays, hosting its annual Winter Wonderland with a giant tree, festive markets, and carriage rides. The Blue Pig Tavern is the place for a hearty bowl of chowder or roast chicken by the fire.

    What to Know Before You Go

    • Open almost year-round; Winter Wonderland typically runs late November through December.  Hotel closes for a brief refresh after the holidays.
    • On-site parking is available for hotel guests.
    • The Blue Pig Tavern accepts reservations.
    • Family-friendly and walkable to Washington Street Mall.

    Fun Fact
    Four U.S. Presidents have vacationed at Congress Hall — Franklin Pierce, James Buchanan, Ulysses S. Grant, and Benjamin Harrison.