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Place to Stay: Inns & Historic Stays

  • 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

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    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

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    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.

  • 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

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    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.

  • The Bay Resort – Dewey Beach, DE

    The Bay Resort – Dewey Beach, DE

    The Bay Resort

    Dewey Beach, DE

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    Photo Caption The Bay Resort’s private dock overlooking Rehoboth Bay. 📸 The Bay Resort

    The Bay Resort
    • Address: 126 Bellevue St, Dewey Beach, DE 19971
    • State: Delaware
    • Website: https://bayresort.com/

    Overview
    The Bay Resort sits along a quiet stretch of Rehoboth Bay, offering simple, comfortable rooms with a peaceful waterfront setting. With private docks, a small pool, and easy access to Dewey Beach’s restaurants and shoreline, it blends the charm of a classic coastal inn with the calm of a bayside escape.

    Why It’s Worth a Stop
    Guests love the sunsets — some of the best in the area — and the ability to fish or launch kayaks right from the resort’s private pier. It’s close to Dewey’s energy but tucked away just enough to feel relaxed.

    What to Know Before You Go

    • Many rooms offer private balconies overlooking the bay.
    • Outdoor pool is open seasonally.
    • A short walk to the ocean beach and Dewey’s main strip.
    • Private pier available for fishing and paddling.
    • Rooms are clean and modest; the bay views are the highlight.

    Fun Fact
    The resort’s private floating dock often attracts herons, egrets, and occasional dolphins passing through the bay.

  • Atlantic View Hotel – Dewey Beach, DE

    Atlantic View Hotel – Dewey Beach, DE

    Atlantic View Hotel

    Dewey Beach, DE

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    Atlantic View Hotel in Dewey Beach, offering oceanfront rooms and direct beach access. 📸 Atlantic View Hotel

    Atlantic View Hotel
    • Address: 2 Clayton St, Dewey Beach, DE 19971
    • State: Delaware
    • Website: https://atlanticview.com/

    Overview
    Atlantic View Hotel is one of the few independently owned beachfront stays in Dewey Beach. With ocean views, direct access to the sand, and a warm, welcoming staff, it blends the simplicity of a classic beach motel with the comfort of an updated coastal inn. It’s a popular choice for couples, families, and travelers looking for a quieter corner of Dewey.

    Why It’s Worth a Stop
    Walk straight from your room to the beach — it’s that close. The atmosphere is low-key and friendly, and many guests come back year after year for the location and the oceanfront rooms.

    What to Know Before You Go

    • Direct beachfront access.
    • Complimentary breakfast and evening cookies.
    • Oceanfront rooms book up early.
    • Outdoor pool available seasonally.
    • Dewey Beach is quieter midweek and in shoulder seasons.

    Fun Fact
    The hotel has been family-owned for more than 40 years, which is rare along the increasingly commercial Delaware beaches.

  • Beach View Hotel – Rehoboth Beach, DE

    Beach View Hotel – Rehoboth Beach, DE

    Beach View Hotel

    Rehoboth Beach, DE

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    Beach View Hotel just steps from the boardwalk and Rehoboth’s Bandstand area. 📸 Beach View Hotel

    Beach View Hotel
    • Address: 6 Wilmington Ave, Rehoboth Beach, DE 19971
    • State: Delaware
    • Website: https://rehobothbeachview.com/

    Overview
    Beach View Hotel is a long-loved Rehoboth stay just off the boardwalk, offering comfortable rooms and classic beach-town hospitality. Overlooking the Bandstand area, it’s close to everything — the shops, the ocean, the evening concerts — yet still keeps a relaxed, family-friendly feel.

    Why It’s Worth a Stop
    It’s hard to beat the convenience. Roll out of bed and be on the beach in minutes, or grab a coffee and stroll the boardwalk before the crowds. The staff is known for being warm and helpful, making the stay feel personal.

    What to Know Before You Go

    • Complimentary breakfast and afternoon cookies.
    • Outdoor pool available in season.
    • Many rooms offer partial ocean views.
    • Free parking on-site (a major perk).
    • Located steps from the Rehoboth Bandstand and Beach.

    Fun Fact
    Beach View Hotel sits just a few feet from the site of Rehoboth’s original 19th-century beachfront cottages.

  • The Avenue Inn & Spa – Rehoboth Beach, DE

    The Avenue Inn & Spa – Rehoboth Beach, DE

    The Avenue Inn & Spa

    Rehoboth Beach, DE

    the-avenue-inn-and-spa-rehoboth-beach-de
    The Avenue Inn in downtown Rehoboth Beach, just a short walk from the sand. 📸 The Avenue Inn and Spa

    The Avenue Inn & Spa
    • Address: 33 Wilmington Ave, Rehoboth Beach, DE 19971
    • State: Delaware
    • Website: https://avenueinn.com/

    Overview
    The Avenue Inn blends classic beach-town hospitality with updated, comfortable rooms just steps from the heart of Rehoboth Beach. It still feels like an old-school coastal hotel — friendly, relaxed, and close to the boardwalk — but with the modern touches travelers appreciate. It’s a reliable, easygoing place to settle in for a weekend.

    Why It’s Worth a Stop
    Its location is ideal: close enough to walk everywhere, yet tucked just off the main drag so evenings stay quiet. Travelers love the welcoming atmosphere, complimentary amenities, and the mix of convenience and comfort.

    What to Know Before You Go

    • Short walk to the beach and boardwalk.
    • Indoor pool and hot tub available year-round.
    • Complimentary happy hour and cookies offered daily.
    • Parking included, a major perk in Rehoboth.
    • Rooms vary from classic to more modern styles.

    Fun Fact
    The hotel has been a Rehoboth favorite for decades, beginning as a simple beach inn before expanding into its current footprint.

  • Saybrook Point Resort & Marina – Old Saybrook, CT

    Saybrook Point Resort & Marina – Old Saybrook, CT

    Saybrook Point Resort & Marina

    Old Saybrook, CT

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    Coastal charm, quiet mornings, and sunsets you’ll want to toast—Saybrook Point makes it easy to stay a little longer. 📸 Saybrook Point Resort & Marina

    White Gate Farm
    • Address: 2 Bridge Street, Old Saybrook, CT
    • State: Connecticut
    • Website: https://www.saybrook.com/

    Overview:
    Tucked where the Connecticut River meets Long Island Sound, Saybrook Point Resort & Marina blends seaside elegance with New England charm. This upscale resort offers thoughtfully appointed rooms, a waterfront marina, spa, wellness center, fine dining, and sweeping coastal views—whether you’re here for a quiet retreat or a special celebration. Guests can choose to stay in the main inn, the historic Three Stories guesthouse, or the romantic Lighthouse Suite perched right over the water.

    Why It’s Worth a Stop:
    Saybrook Point delivers a full resort experience, from award-winning farm-to-table cuisine at Fresh Salt to the serene Sanno Spa. With indoor and outdoor pools, a marina with seasonal events, and close proximity to downtown Old Saybrook and scenic shoreline drives, it’s the kind of place that makes even a short stay feel like a true getaway.

    What to Know Before You Go:
    • Offers a variety of accommodations, including waterfront suites and a stand-alone lighthouse suite
    • On-site amenities include full-service spa, fitness classes, marina, and fine dining
    • Walkable to the shops and galleries of Old Saybrook
    • Check the calendar for seasonal packages and special events
    • Ideal for romantic escapes, weddings, and wellness weekends

    Fun Fact:
    The property sits near the site of the original Saybrook Colony, one of the earliest settlements in Connecticut, founded in 1635.