36+ Vacation Rentals Near Glenwood Park |
  1. USA
  2. Virginia
  3. Middleburg
  4. Glenwood Park

Stayifyoudare - Vacation Rentals in Glenwood Park

Property Image From $553
         

10.0 (77 Reviews)
House
'Anny's Farm House' in Round Hill Wine Country!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Property Image From $729
         

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9.8 (40 Reviews)
Resort
Salamander Resort and Spa
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $558
         

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10.0 (101 Reviews)
House
204 m² House ∙ 4 bedrooms ∙ 8 guests
  • 2195 ft² House
  • Air Conditioner
  • TV
  • Security/Safety

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Property Image From $1,693
         

New
House
Grand 9BR Provenance Manor Ideal for Gatherings
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Property Image From $306
         

10.0 (47 Reviews)
Cottage
18th Century Stone Cottage minutes from historic Middleburg
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $253
         

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9.7 (11 Reviews)
Apartment
Magnificent Middleburg Getaway
  • Air Conditioner
  • Parking
  • View

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Property Image From $464
         

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New
House
240 m² Motel ∙ 4 guests
  • 2583 ft² House
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $430
         

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9.6 (390 Reviews)
Hotel
The Red Fox Inn & Tavern
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $395
         

10.0 (17 Reviews)
House
Spacious Modern Home on Middleburg Horse Farm
  • Air Conditioner
  • Parking
  • TV

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Property Image From $501
         

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New
House
Annys Farm House in Round Hill Wine Country!
  • Parking
  • Security/Safety
  • Sports/Activities

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Property Image From $456
         

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9.6 (47 Reviews)
Hotel
Goodstone Inn & Restaurant
  • Air Conditioner
  • Pool
  • TV

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Property Image From $202
         

10.0 (9 Reviews)
House
super cosy cottage with high speed internet!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $325
         

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8.7 (28 Reviews)
Hotel
Goodstone Inn & Restaurant
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $650
         

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9.2 (365 Reviews)
Resort
Salamander Resort And Spa
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $286
         

10.0 (2 Reviews)
Apartment
Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops
  • Air Conditioner
  • Parking
  • TV

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Property Image From $314
         

9.4 (8 Reviews)
Apartment
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image
New
From $4,002
         

New
House
Private & Exclusive 100 acre Middleburg Estate
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Property Image From $1,406
         

New
House
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Property Image From $888
         

New
Apartment
Middleburg Famous Horse Farm
  • Air Conditioner
  • Pool
  • Balcony/Terrace

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Property Image
New
From $594
         

New
House
Rural retreat near Middleburg
  • Security/Safety
  • Child Friendly
  • Laundry

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Property Image From $201
         

10.0 (81 Reviews)
Cottage
Middleburg address - Charming Cottage with super location in country setting
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $335
         

10.0 (37 Reviews)
Cottage
Lovely Guest House 2.5 miles from downtown Middleburg
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,595
         

10.0 (13 Reviews)
House
Historic Equestrian Estate in Middleburg Hunt Country
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $190
         

10.0 (5 Reviews)
House
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Glenwood Park.

Weather in Glenwood Park

View the weather forecast for Glenwood Park before booking your Glenwood Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Glenwood Park, VA

Stayifyoudare offers a large selection of top attractions around Glenwood Park. Research things to do on your vacation before you visit Glenwood Park.


Stone Tower Winery Bluemont Vineyard Tudor Day Spa Greenhill Winery & Vineyards Barrel Oak Winery Chrysalis Vineyards Delaplane Cellars Bull Run Country Club Round Hill Arts Center The Barns at Hamilton Station Vineyards Quattro Goomba's Winery Twin Oaks Tavern Winery Watermelon Park Campground K & S Pewter Holy Cross Abbey Meredyth Vineyards Sky Meadows State Park Hill High Country Store Bogati Bodega & Winery