Chester Gap Holiday Rentals, Virginia: Private House Rentals

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Our top choices for Chester Gap hotels

A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

A modern kitchen with a flat-screen TV, a microwave, and a refrigerator.

A large conference room with a patterned carpet, recessed ceiling lights, and artwork on the walls.

1. Hampton Inn Front Royal

Front Royal

Grace

฿3,949

฿4,395 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

A conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".

A hotel reception area with a counter, a vending machine, and a sign indicating a minibar.

2. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

฿4,659

฿5,205 total

includes taxes & fees

1 Nov - 2 Nov

A restaurant interior with a bar area, seating, and artwork on the walls.

An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.

A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

3. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Jeffrey

฿4,269

฿4,709 total

includes taxes & fees

11 Nov - 12 Nov

A hotel lobby with a reception desk, seating area, and a fireplace.

A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

A hotel room with a red carpet, white sofas, a reception desk, and a large window with blinds.

A hotel room with two beds, a large window with curtains, an air conditioning unit, a nightstand with a phone and clock, and a wall with a waterfall painting.

4. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Rosilene

฿2,106

฿2,344 total

includes taxes & fees

4 Nov - 5 Nov

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

A view of a swimming pool with a fountain, surrounded by a fence and greenery, with mountains in the background.

A bathroom with a large window, a bathtub, and a view of a green landscape.

A dining area with a table set for two, featuring a bowl of bread, a glass of wine, and a vase of flowers.

5. Glen Gordon Manor

Huntly

Alexander and Judith

฿9,325

฿10,752 total

includes taxes & fees

16 Nov - 17 Nov

A hotel lobby with a reception desk, seating area with a round table, and a bar.

A hotel reception desk with a computer, two chairs, and a large mirror.

A multi-story hotel with a prominent sign for Marriott.

A swimming pool with a tiled deck, chairs, and a sign indicating no lifeguard on duty.

6. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

฿3,779

฿4,206 total

includes taxes & fees

17 Nov - 18 Nov

A hotel room with a television, desk, chair, sofa, and kitchenette.

A hotel dining area with multiple tables and chairs, large windows, and a television screen.

7. Comfort Inn & Suites Winchester

Winchester

Lisa

฿3,354

฿3,733 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.

A room with two grey armchairs, a small table with a vase of flowers, a television mounted on the wall, and a desk with a computer.

A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.

A breakfast counter with various food items and a coffee machine.

8. Baymont by Wyndham Front Royal Near Shenandoah National Park

Front Royal

pieter

฿1,937

฿2,156 total

includes taxes & fees

4 Nov - 5 Nov

A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.

A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.

A modern breakfast area with seating, a counter for hot food, and a view of the outdoors.

9. Holiday Inn Express Winchester South-Stephens City by IHG

Stephens City

Michael

฿2,774

฿3,088 total

includes taxes & fees

15 Nov - 16 Nov

A hotel lobby with a reception desk, a check-in counter, a seating area with chairs, and a dining area in the background.

A modern hotel lobby with a clear exit sign, a reception desk, and a seating area with red chairs.

A hotel with a green roof, a covered entrance, and a sign that reads "RAMADA".

A hotel lobby with a polished tile floor, a reception desk, and seating area with white chairs.

10. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

Susan

฿2,529

฿2,814 total

includes taxes & fees

1 Nov - 2 Nov

An open doorway leading to a room with a dining table and chairs, a sofa, and a window.

A modern living room with a sofa, a glass coffee table, a bookshelf, and a mounted deer head.

A building with a yellow door and a sign that reads "The White Moose Inn."

A modern bedroom with a bed, bedside table, and a glass table with chairs.

11. White Moose Inn

Washington

Blake

฿10,498

฿11,317 total

includes taxes & fees

1 Nov - 2 Nov

A covered outdoor area with a table and chairs, a brick wall, and a metal railing.

A hotel room with two beds, a desk, and a chair.

A brick building with a sign reading "Motel" and a neon sign for "Relax Inn" on the right.

A bathroom with a shower, toilet, and a bathtub.

12. Relax Inn Motel

Front Royal

Sarah

฿2,178

฿2,425 total

includes taxes & fees

18 Oct - 19 Oct

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

A woman using a stationary bike in a gym with red walls and multiple exercise machines.

A poolside area with lounge chairs and a stack of towels on a table.

A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

13. Country Inn & Suites by Radisson, Winchester, VA

Winchester

Allen

฿2,948

฿3,281 total

includes taxes & fees

8 Nov - 9 Nov

A rustic interior with wooden tables and chairs, a brick floor, and a wooden ceiling.

A cozy living room with a fireplace, patterned chairs, and a dining area with wooden furniture.

A large brick building with a central entrance, multiple windows, and a covered walkway.

14. Wayside Inn

Middletown

Judy

฿2,279

฿2,849 total

includes taxes & fees

19 Oct - 20 Oct

A spacious lobby with a stone fireplace, red chairs, a wooden staircase, and a flat-screen TV mounted on the wall.

A stainless steel kitchen with a built-in water dispenser and a window with blinds.

A hotel room with a large bed, a ceiling fan, a nightstand, a window with curtains, and a view of the ocean.

A hotel lobby with a wooden staircase, a reception desk, and red chairs.

15. Motel 6 Front Royal, VA

Front Royal

ERIN

฿1,960

฿2,181 total

includes taxes & fees

4 Nov - 5 Nov

A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.

A two-story building with a brick facade and a beige exterior.

A gym with an elliptical, dumbbells, a treadmill, and a wall-mounted phone.

A hotel room with two beds, a desk, a television, and a window with curtains.

16. Quality Inn Stephens City - Winchester South

Stephens City

Jeanne

฿2,820

฿3,139 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with stainless steel appliances, wooden ceiling, and pendant lighting.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn and trees.

A modern kitchen with wooden ceiling, a central island, and pendant lighting.

A grassy outdoor area with wooden chairs and a white fence.

17. The Foster Harris House

Washington

John

฿15,011

฿16,182 total

includes taxes & fees

25 Oct - 26 Oct

A building with a sign reading "OFFICE" above the entrance.

A small bathroom with a white sink, a toilet, and a wooden shelf above the toilet holding towels.

A building with a stone facade, a covered walkway, and a tree with autumn leaves.

A hotel room with two beds, a nightstand, a lamp, a heater, and two framed pictures on the wall.

18. Blue Ridge Motel

Front Royal

Karen

฿1,955

฿2,177 total

includes taxes & fees

17 Nov - 18 Nov

A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

A bedroom with a bed, bench, and a view of the kitchen.

A two-story house with a sign reading "Gay Street Inn" in front.

A dining table set with clear glassware and a vase of white flowers.

19. Gay Street Inn

Washington

Kathryn

฿10,829

฿11,673 total

includes taxes & fees

26 Oct - 27 Oct

A covered porch with white columns, a bench, and hanging flower baskets.

A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

A dining area with tables set for service, large windows with views of greenery, and a chandelier.

A two-story house with a swimming pool, outdoor furniture, and a covered patio area.

20. L'Auberge Provencale Inn & Restaurant

Boyce

Henry

฿9,652

฿10,647 total

includes taxes & fees

2 Nov - 3 Nov

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Learn more about Chester Gap

Check out popular sights like Shenandoah National Park as you discover the local area in Chester Gap.

See all hotels in Chester Gap

Top Chester Gap Hotel Reviews

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good

"Clean room, nice staff, and everything was orderly. For the price, its ok."

Quality Inn Stephens City - Winchester South

8/10 Good

"The breakfast was disappointing in that the scrambled eggs and sausage were tasteless. The coffee was bland. The ptac was noisy. The room was very clean and quiet."

Fairfield Inn & Suites Strasburg Shenandoah Valley

10/10 Excellent

"Clean, upkeep was good, breakfast was very good. Ice machine on our floor wasn’t working but when to the next floor for ice. We loved the Shower."

Hampton Inn Front Royal

10/10 Excellent

"The room was nice and clean. Everything was laid so that everything was easy to use. It had a large TV that was on a swivel so you could move it to where it was needed. Just to cut this short it was an excellent place and had a nice breakfast."

Comfort Inn & Suites Winchester

10/10 Excellent

"Stay was great! Room as big and clean. Front deak staff was super friendly and helpful with restaurant suggestions"

Holiday Inn Express Winchester South-Stephens City by IHG

10/10 Excellent

"Nice facility, easy to get to. Clean and functional room. NICE breakfast buffet!"

Motel 6 Front Royal, VA

10/10 Excellent

"We accidentally booked the wrong kind of room and the staff was very understanding and helpful."

Hillside

8/10 Good

"View and location outside the park were great. Room and bathroom were tight. Great for an overnight stay but not comfy home base for a long term stay due to Lack of free space in the room. Town not too far away for dining and necessities. Cost for having a pet seemed steep in comparison to room cost."

TownePlace Suites by Marriott Front Royal

10/10 Excellent

"The hotel is really nice, seems new. The decor is lovely and the rooms are big. The breakfast isn't as fancy as some but was very good. I did have a problem with the dishwasher beeping and a staff member came right over and reset it. I would certainly stay again."

More cheap stays in Chester Gap

Baymont by Wyndham Front Royal Near Shenandoah National Park

10 S Commerce Ave Front Royal VA

฿1,937

฿2,156 total

4 Nov - 5 Nov

includes taxes & fees

Super 8 by Wyndham Front Royal Near Shenandoah National Park

111 South St Front Royal VA

฿2,106

฿2,344 total

4 Nov - 5 Nov

includes taxes & fees

7.6/10 Good! (1,001 reviews)

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

฿2,529

฿2,814 total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,018 reviews)

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

฿3,354

฿3,733 total

15 Nov - 16 Nov

includes taxes & fees

9.4/10 Exceptional! (1,132 reviews)

Hillside

1460 US Highway 211 East Luray VA

฿3,659

฿4,219 total

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

฿3,949

฿4,395 total

15 Nov - 16 Nov

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Chester Gap?

Hillside, located 19.1 mi (30.8 km) from the heart of Chester Gap, is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Comfort Inn & Suites Winchester and Ramada by Wyndham Strasburg/Shenandoah Valley. See all available top hotels, or vacation rentals in Chester Gap.

If I need to cancel my hotel reservation in Chester Gap, will I receive a refund?

Yes! Most room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester Gap.

What is staying in Chester Gap like?

Visitors will definitely enjoy all that Chester Gap has to offer. A top sight in the city is Shenandoah National Park. In Chester Gap, there are 3 hotels and other accommodation options to choose from. Find out more about Chester Gap.

What should I do while I'm visiting Chester Gap?

A favourite place to visit is Shenandoah National Park. You'll also find Rappahannock Cellars and Dickey Ridge Visitor Center in the area. Take a look at what more there is to see and do in Expedia's Chester Gap guide.

What's the seasonal weather in Chester Gap?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Chester Gap is 1184 mm.

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Find hotels in Chester Gap, VA from ฿2,156

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester Gap

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester Gap hotels

1. Hampton Inn Front Royal

2. TownePlace Suites by Marriott Front Royal

3. DoubleTree by Hilton Front Royal Blue Ridge Shadows

4. Super 8 by Wyndham Front Royal Near Shenandoah National Park

5. Glen Gordon Manor

6. Fairfield Inn & Suites Strasburg Shenandoah Valley

7. Comfort Inn & Suites Winchester

8. Baymont by Wyndham Front Royal Near Shenandoah National Park

9. Holiday Inn Express Winchester South-Stephens City by IHG

10. Ramada by Wyndham Strasburg/Shenandoah Valley

11. White Moose Inn

12. Relax Inn Motel

13. Country Inn & Suites by Radisson, Winchester, VA

14. Wayside Inn

15. Motel 6 Front Royal, VA

16. Quality Inn Stephens City - Winchester South

17. The Foster Harris House

18. Blue Ridge Motel

19. Gay Street Inn

20. L'Auberge Provencale Inn & Restaurant

Learn more about Chester Gap

Top Chester Gap Hotel Reviews

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Quality Inn Stephens City - Winchester South

Fairfield Inn & Suites Strasburg Shenandoah Valley

Hampton Inn Front Royal

Comfort Inn & Suites Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Motel 6 Front Royal, VA

Hillside

TownePlace Suites by Marriott Front Royal

More cheap stays in Chester Gap

Baymont by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Ramada by Wyndham Strasburg/Shenandoah Valley

Comfort Inn & Suites Winchester

Hillside

Hampton Inn Front Royal

Frequently asked questions

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