Places to stay near Gypsy Hill Park

Bee & Key—Staunton downtown

This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. in downtown Staunton. 2BR/1BA can sleep up to 6 if you don’t mind being cozy! • king bed in main bedroom (2) • day bed with trundle in small adjoining bedroom (2) • sofa bed in living room (1) • good air mattress (1) Bee & Key is a few steps from the restaurants and shops of our vibrant downtown, plus Blackfriar’s Playhouse, Woodrow Wilson Museum, Mary Baldwin University and the Amtrak station.

Mid-Century Downtown Staunton Loft

When 3 is a crowd, try a romantic hideaway for 2. Just uphill from the downtown restaurants. A mid-century loft in a 1900 house. Our neighbor is the Stuart School. Perfect for your exploration of Staunton and the Valley. The apartment is the top floor of this hill-hugging four-story, yet it is only one floor from the entrance. A shared washer-and-dryer is on the one floor down. Fiber optic wifi, and smart TV provides work and entertainment opportunities. Parking is free on the street.

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Queen City Hideaway

Imagine waking up to stunning mountain views, brewing coffee on your private deck, and planning your day exploring Staunton's vibrant downtown. Fully stocked! Need for nothing! Unwind in the heart of Staunton's historic charm! Sip coffee on your private deck overlooking Staunton's vibrant cityscape and rolling mountains. Binge your favorite show on our smart TV, and whip up a meal in the stocked kitchen. Walk to restaurants, shops, or the theater. Book your stay today and start planning!

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

Third & Thornrose, Staunton Condominium

Our guests stay upstairs in our 1929 American Foursquare house. Central air; separate entrance, wooden floors. Daily, weekly or monthly rates. Small, fully-equipped kitchen with stove and refrigerator, small dining room. The bathroom has a tub and shower. Television with Netflix. Wifi and off-street parking. Two bedrooms (queen-sized bed, two XL twin beds), living room. Short walk to Gypsy Hill Park, 1 mile to historic downtown (Trolley). Small town, Big Magic!

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

The Red Hen Historic Cottage

Welcome to The Red Hen, a newly renovated, historic home in downtown Staunton. You'll be just steps from all of the fantastic dining, shopping, architecture, and entertainment that the city has to offer! This peaceful, stylish home has the best of both worlds; loads of historic charm with all of the modern upgrades you could hope for. Enjoy the spaciousness, the fun vintage elements, the comfort, and the incredible location!

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

Green on New - Central Location and Staunton Charm

The Little Green House on N. New St. is a historic home stylishly and lovingly renovated and decorated to suit your next getaway! This cheerful home is centrally located in Downtown Staunton and is just a 10 minute stroll to the iconic shops and dining located on East Beverley Street. With two queen bedrooms and a spacious backyard, this home is perfect for a small family, a couple, or even two couples.

Walker's dream. Close to downtown.

Centrally located near the library, Gypsy Hill Park, and downtown Staunton, our private, walkout basement apartment has individually controlled heating and air conditioning. It includes a brick patio, private rear entrance and historic details from the late 1800's. It is generally quiet, but you may sometimes hear the two adults upstairs. Come enjoy this peaceful and centrally-located space.

The Storefront: Downtown Staunton + Unique Stay

Welcome to The Storefront: A Very Small Hotel. The Storefront is located right in the heart of downtown Staunton. The Storefront was built in the early 1900's and was previously a tea shop before becoming a vacation destination. It's like having your own little townhouse in the heart of Staunton's historic district! Keep your car parked and walk everywhere you need to go.