
Places to stay near Gypsy Hill Park
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Top-rated holiday rentals near Gypsy Hill Park
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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.

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!

Enchanting, historic home - short walk to downtown
Sweet Darling House is a 19th Century home in the renowned Gospel Hill neighborhood, and a short walk (0.7 miles) to downtown Staunton. The house is situated on a beautiful outdoor wooded space, a wildlife viewer's dream!! A perfect blend of 1800s charm & modern comforts. Steps away from our award-winning, historic downtown, with boutiques, cafes, restaurants and art. Enjoy a unique blend of history and luxury in this quaint Virginia gem!

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.

Gibson's Warehouse No. 1- Overlooking the City!!
Welcome to Gibson's Warehouse No. 1 - A newly renovated, modern warehouse in downtown Staunton, VA. This historic building was designed in 1905, by renowned architect, T.J. Collins. The location is central, safe and packed full of restaurants, unique shops, breweries, green space and just about anything else your heart desires.
Popular amenities for holiday rentals near Gypsy Hill Park
Other top sights near Gypsy Hill Park
Condo rentals with Wi-Fi

Panoramic Sunsets Mountain Views Pool $99 Midweek

1 bedroom condo, close to hikes & breweries & pool

Luxury Condo in the Sky! Finest in Wintergreen!

Extremely private, HOA pool/stair-free entry

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Beautiful Mountain Getaway - Walk to Everything!

3 BR 3 BA, 2 story condo in Highlands

Cozy Condo on the mountain at Wintergreen!
Family-friendly house rentals

Mountain Views, Hot Tub, Treehouse & Game Room

Foresthill Farm

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

Little Yellow House: Walk to Downtown Staunton

Mountain Overlook House - Blue Ridge Parkway

The Landmark: Luxury In Downtown Staunton

Blackwood Air B & B

Willow Grove-Hot Tub+Views-3.5 acres
Apartment rentals with air conditioning

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

Willow Ridge

Downtown Luxe: Luxury Vintage + Downtown

Wildflowers Artist House

Updated Victorian Welcomes You & Your Pets

⭐Private Apartment Footsteps From Downtown

Queen City Hideaway

Little Yellow Hideaway (Apt in Historic Home)
Other great holiday rentals near Gypsy Hill Park

The Firefly Cottage

Serenity by the Stream

Magical Cabin Nestled by Creeks, Shenandoah Valley

CloudPointe Retreat

Little Cabin in the Woods is quiet and secluded!

The Sanctuary

The Staunton Hideaway

Sweet Retreat-4 beds-2.5 bath!
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Early Mountain Winery
- University of Virginia
- Monticello
- Devils Backbone Brewing Co Basecamp
- Wintergreen Resort
- Glass House Winery
- Cardinal Point 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
- John Paul Jones Arena
- James Monroe's Highland
- IX Art Park
- Grand Caverns
- James River State Park
- Cass Scenic Railroad State Park





