Wine Country Villas - Vacation Rentals in Chester Gap

Hazegrov in Virginia Horse and Wine Countryn From US $181
         

9.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Chester Gap

Over 87+ Luxury Places to Stay in or Near Chester Gap
Tranquil 4-bedroom lodge in Front Royal with AC, WiFi From US $1,655
         

Delicious Cabin Wine Country Retreat w/Hot Tub From US $565
         

9.8 (10 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Skyland Hideaway | Mountain Cabin w/Hot Tub From US $548
         

10.0 (15 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
The Pond Cabin: Hot Tub & Stocked Pond From US $499
         

10.0 (33 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Security/Safety
The Juniper Cabin Cozy Hideaway w/Hot Tub From US $497
         

10.0 (22 Reviews)
Cabin
  • Air Conditioner
  • Pet Friendly
  • TV

Top-Rated Vacation Rentals with a Pool in Chester Gap

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Chester Gap
Glen Gordon Manor From US $349
         

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9.8 (94 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Baymont by Wyndham Front Royal Near Shenandoah National Park From US $64
         

Charming modern home in the mountains From US $285
         

New
House
  • Air Conditioner
  • Pool
  • Balcony/Terrace

Pet-Friendly Vacation Rentals in Chester Gap

Over 42+ Pet-Friendly Vacation Rentals in or Near Chester Gap
The Nest at Chester Gap From US $463
         

10.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Mountain Retreat with Deck and Hot Tub! From US $200
         

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9.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
New - Modern Mountain Retreat w/Hot tub and view! From US $475
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries From US $307
         

Hot Tub Mountain View Dog Friendly Modern Chalet From US $229
         

10.0 (12 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
The Grape Escape - A-Frame Cabin From US $244
         

10.0 (11 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Cedarbank Cabin in Virginia Wine Country From US $275
         

10.0 (8 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
New - The Skyline Flat From US $112
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chester Gap

Over 9+ Large Vacation Homes & Villas in or Near Chester Gap
Spacious 5-bedroom house with WiFi, AC in charming Front Royal From US $242
         

Mountain Home Bed & Breakfast From US $151
         

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9.3 (242 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Mountain Views in Buena Vista Farm - Unit A From US $170
         

9.8 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Marriott Ranch Bed and Breakfast From US $169
         

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9.3 (41 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Front Royal 5 bdrm 4 bth National park w/driveway From US $235
         

4.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious modern home with driveway parking and nearly one acre From US $448
         

Mountain Views in Buena Vista Farm - Entire Home From US $182
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Chester Gap

Over 2+ Wheelchair Accessible Vacation Homes in or Near Chester Gap
Rustic Cabin with Mtn Views, Deck and Fire Pit! From US $189
         

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New
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly

Chester Gap Varoom and Airbnb Places to Stay Under $200

Over 17+ Chester Gap Varoom and Airbnb Places to Stay Under $200
Apple Mountain Retreat From US $163
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Front Royal Studio with Mtn Views and Brick Oven From US $158
         

9.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
Home 2 Mi to Shenandoah Nat'l Park & Skyline Drive From US $188
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Front Royal Studio w/Mtn Views & Brick Oven From US $162
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Chic Front Royal Retreat Near Shenandoah River! From US $156
         

9.8 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy studio close to Skyline Drive, Hiking, and Main Street. From US $189
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Front Royal Retreat on 3 Acres w/Mtn Views! From US $169
         

8.4 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Chester Gap

Over 30+ Instantly Bookable Vacation Homes in or Near Chester Gap
Big Sunny Family House From US $416
         

10.0 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Mountain cabin near national park & wineries From US $420
         

10.0 (28 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Beau Ridge Cabin (Little Cabin with a big view) From US $261
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern Mountain Retreat w/Deck + Hot Tub! From US $267
         

9.8 (79 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hidden Gem on Hidden Valley Lane From US $441
         

9.6 (27 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Cute cabin retreat near Shenandoah National Park and pet friendly! From US $242
         

About Chester Gap Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Winecountryvillas Chester Gap, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester Gap. Places to stay near Chester Gap are 1000 ft² on average, with prices averaging $181 a night.

Winecountryvillas makes it easy and safe to find and compare vacation rentals in Chester Gap with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chester Gap

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Use these Quick Filters to Find a Vacation Rental in Chester Gap

Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas 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 Chester Gap.

Weather in Chester Gap

View the weather forecast for Chester Gap before booking your Chester Gap 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

Other Places to Stay Near Chester Gap, VA