A guide with the best places to stay in The Best Places to Stay in WILLIAMSBURG & THE CHESAPEAKE BAY

Whether you’re seeking a cozy Airbnb, historic waterfront inn, boutique hotel on a winery, or luxurious resort, our guide on the best places to stay in Williamsburg & The Chesapeake Bay offer something for everyone. You’ll find excellent options for those visiting town or locals looking for a staycation. Don’t forget to tell them The Scout Guide sent you when you book your stay!

The Inn at Warner Hall (4750 Warner Hall Road, Gloucester, VA 23061). Disconnect from the hustle & bustle of city life while experiencing romance, history and stunning waterfront views! Instagram

Wedmore Place (5800 Wessex Hundred, Williamsburg, VA 23185). This boutique hotel at the Williamsburg Winery will have you feeling like you’re in old world Europe while boasting delicious dining and wine all on its picturesque property. Instagram

Kingsmill Resort (1010 Kingsmill Road, Williamsburg, VA 23185). Experience luxury in Williamsburg! Instagram

Bitt of Home (Gloucester, VA). Beautifully vintage 2 bedroom home, centrally located, in Gloucester Courthouse.

The Loft of Main Street (Gloucester, VA). Completely Renovated Condo on Historic Main Street in Gloucester right next to the Art Center, boutique shops, a spa, incredible dining and more!

Explore our other Insider Guides: The Best Places to Eat in Williamsburg & The Chesapeake Bay and The Best Places to Shop in Williamsburg & The Chesapeake Bay.

Businesses in bold are members of The Scout Guide Williamsburg & The Chesapeake Bay.