
Places to stay near Gypsy Hill Park
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Gypsy Hill Park
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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!

Downtown Luxe: Luxury Vintage + Downtown
Come enjoy this newly remodeled moody and eclectic luxury apartment during your stay in Staunton Virginia! This 2-bed, 1-bath apartment places you at the epicenter of a vibrant downtown culture while surrounding you with the style, luxurious details, and enchanting ease of a well-appointed home. We are located a minute walk from all that downtown has to offer. Our unit sleeps 6 and parking is provided with our parking pass. Please make sure to return it after use:).

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!

* Award-Winning Renovation * Ideal Location *
— Off-Street Parking — Cleaning & Linens taken care of for you — Prepare a meal in the fully equipped kitchen. Relax on the porch as the sun sets behind the nearby mountains. Or sink into your own king-size bed with a good book. This downtown home was painstakingly renovated to highlight its historic character and is a proud recipient of the Historic Staunton Foundation's 2021 Residential Rehabilitation Award. Welcome to NEWTOWN RETREAT!

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.

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.

The Pop Inn: Family Destination, Walk Dwntwn
Talk about creative spaces! 90’s nostalgia and pop art fanatics will love the fun gaming, comics, and pop culture theme. The design of this newly renovated, brilliantly stylish 2 bedroom, 1 bathroom apartment will ignite your imagination. Plus we are located just 1 block from Gypsy Hill Park and 1 mile from historic downtown Staunton.

the apARTment on Church
Occupying the top floor of our renovated 1860s house is a charming hideway filled with original art, eclectic furnishings, a fully stocked kitchen and bathroom, and comfortable full sized bed. The living room has a fold out dining table and futon. The house is within walking distance to everything downtown, on a very nice street.
Popular amenities for holiday rentals near Gypsy Hill Park
Other top sights near Gypsy Hill Park
Condo rentals with Wi-Fi

1 bedroom condo, close to hikes & breweries & pool

Panoramic Sunsets Mountain Views Pool $99 Midweek

Luxury Condo in the Sky! Finest in Wintergreen!

Beautiful Mountain Getaway - Walk to Everything!

Extremely private, HOA pool/stair-free entry

Where the Trail Ends

Panoramic Peak: Wintergreen Condo with Views

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Family-friendly house rentals

Mountain Views, Hot Tub, Treehouse & Game Room

Enchanting, historic home - short walk to downtown

Staunton Escape 👑King Bd, washer+dryer+Wifi+Fence

Foresthill Farm

Mountain Overlook House - Blue Ridge Parkway

We got the Beet!

Little Yellow House: Walk to Downtown Staunton

Blackwood Air B & B
Apartment rentals with air conditioning

Big Blue #1: Spacious&Modern. Close to Downtown

Updated Victorian Welcomes You & Your Pets

Willow Ridge

Wildflowers Artist House

⭐Private Apartment Footsteps From Downtown

Little Yellow Hideaway (Apt in Historic Home)

The Barn at Haden near Wineries and C'ville

Cozy stay with scenic views on a horse farmette
Other great holiday rentals near Gypsy Hill Park

The Firefly Cottage

Serenity by the Stream

The Staunton Hideaway

CloudPointe Retreat

Sweet Retreat-4 beds-2.5 bath!

Cozy Craftsman: Newly Renovated/Downtown Staunton

Queen City Twin of Staunton VA

All-American Cottage by the Park
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Early Mountain Winery
- University of Virginia
- Monticello
- Devils Backbone Brewing Co Basecamp
- Wintergreen Resort
- Cardinal Point Winery
- Glass House Winery
- Blenheim Vineyards
- James Madison University
- Virginia Horse Center
- Natural Bridge State Park
- The Rotunda
- Downtown Mall
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Frontier Culture Museum
- James Monroe's Highland
- IX Art Park
- John Paul Jones Arena
- Grand Caverns
- James River State Park
- Cass Scenic Railroad State Park





