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Private Pool
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Hot Tub
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Breakfast
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Parking

Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the Middletown offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Winchester
- ·
- Strasburg
- 1.63 mi to center
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Breakfast
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Parking
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Pool
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Kitchen
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Breakfast
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Parking
-
Pool
-
Kitchen
- Winchester
- ·
- Stephens City
- 0.34 mi to center
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Parking
-
Pool
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Air Conditioner
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Internet
-
Parking
-
Pool
-
Air Conditioner
-
Internet
- Winchester
- ·
- Stephens City
- 0.33 mi to center
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Breakfast
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Parking
-
Pool
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View
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Breakfast
-
Parking
-
Pool
-
View
- Winchester
- ·
- Strasburg
- 1.52 mi to center
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Private Pool
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Parking
-
Pool
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Kitchen
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Private Pool
-
Parking
-
Pool
-
Kitchen
- Winchester
- ·
- Strasburg
- 4.16 mi to center
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Parking
-
Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
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Parking
-
Balcony/Terrace
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View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Virginia
- ·
- Middletown
- 0.02 mi to center
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Parking
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Balcony/Terrace
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Air Conditioner
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Internet
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Parking
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Balcony/Terrace
-
Air Conditioner
-
Internet
- Virginia
- ·
- Middletown
- 4.88 mi to center
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Parking
-
Pool
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Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
-
Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 5.24 mi to center
-
Hot Tub
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Parking
-
Balcony/Terrace
-
View
-
Hot Tub
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Parking
-
Balcony/Terrace
-
View
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 0.36 mi to center
-
Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 4.70 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Strasburg
- 4.16 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Virginia
- ·
- Middletown
- 0.02 mi to center
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Parking
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Balcony/Terrace
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Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Virginia
- ·
- Middletown
- 4.88 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 5.24 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Winchester
- ·
- Stephens City
- 2.72 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Winchester
- ·
- Strasburg
- 4.16 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Virginia
- ·
- Middletown
- 0.02 mi to center
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Parking
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Balcony/Terrace
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Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Virginia
- ·
- Middletown
- 4.88 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 5.24 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Winchester
- ·
- Strasburg
- 4.16 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Virginia
- ·
- Middletown
- 0.02 mi to center
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Virginia
- ·
- Middletown
- 4.88 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 5.24 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
Find the Perfect Resort Vacation in the Middletown
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the Middletown
What are the Top Resort Locations Across the Middletown?
Discover resorts in the most sought-after travel destinations nationwide:
Jackson's Chase Golf Course
Jackson's Chase Golf Course VACATION RENTALSCedar Creek and Belle Grove National Historical Park
Cedar Creek and Belle Grove National Historical Park VACATION RENTALSCedar Creek Battlefield Foundation
Cedar Creek Battlefield Foundation VACATION RENTALSBelle Grove Plantation
Belle Grove Plantation VACATION RENTALSWayside Theater
Wayside Theater VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Middletown. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the Middletown
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Middletown, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the Middletown? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Winchester
- ·
- Strasburg
- 4.70 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Strasburg
- 4.16 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Virginia
- ·
- Middletown
- 4.88 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Star Tannery
- 4.22 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 0.47 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 2.15 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Stephens City
- 4.83 mi to center
-
Hot Tub
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Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Fishers Hill
- 3.18 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Winchester
- ·
- Strasburg
- 5.24 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
- Winchester
- ·
- Strasburg
- 0.36 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Virginia
- ·
- Middletown
- 0.02 mi to center
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Parking
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Balcony/Terrace
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Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
Resorts Vacations FAQs
Which vacation homes in Middletown are best for families?
If you are looking for a family-friendly vacation home in Middletown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middletown:
How many vacation rentals are available in Middletown?
Currently, the total number of properties listed in 2026 is over 41 in the Middletown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Middletown.
More Resorts Vacations to Explore
- Virginia
- ·
- Middletown
- 0.50 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Winchester
- ·
- Strasburg
- 1.04 mi to center
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Parking
-
Air Conditioner
-
Internet
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Wheelchair Accessible
-
Parking
-
Air Conditioner
-
Internet
-
Wheelchair Accessible
- Winchester
- ·
- Stephens City
- 0.34 mi to center
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Parking
-
Pool
-
Air Conditioner
-
Internet
-
Parking
-
Pool
-
Air Conditioner
-
Internet
- Winchester
- ·
- Stephens City
- 0.33 mi to center
-
Breakfast
-
Parking
-
Pool
-
View
-
Breakfast
-
Parking
-
Pool
-
View
- Virginia
- ·
- Middletown
- 0.02 mi to center
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Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Winchester
- ·
- Strasburg
- 1.63 mi to center
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Breakfast
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Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Winchester
- ·
- Front Royal
- 4.44 mi to center
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Private Pool
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Hot Tub
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Breakfast
-
Parking
-
Private Pool
-
Hot Tub
-
Breakfast
-
Parking
- Winchester
- ·
- Strasburg
- 1.52 mi to center
-
Private Pool
-
Parking
-
Pool
-
Kitchen
-
Private Pool
-
Parking
-
Pool
-
Kitchen
- Virginia
- ·
- Middletown
- 0.50 mi to center
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Parking
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Air Conditioner
-
Internet
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Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Winchester
- ·
- Stephens City
- 3.88 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Winchester
- ·
- Strasburg
- 0.37 mi to center
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Kitchen
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Air Conditioner
-
Internet
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Child Friendly
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
- Virginia
- ·
- Fishers Hill
- 8.94 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner