Chester Gap Holiday Rentals, Virginia: Private House Rentals

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Our top choices for Chester Gap hotels

A swimming pool with clear water, surrounded by large windows offering views of greenery.

A modern dining area with tables and chairs, large windows, and a flat-screen TV on the wall.

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 gym with weightlifting equipment, including dumbbells and a bench.

1. Hampton Inn Front Royal

Front Royal

Grace

Rp2.187.389

Rp2.434.564 total

includes taxes & fees

4 Oct - 5 Oct

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 spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.

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

2. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

Rp1.909.355

Rp2.106.017 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.

3. Comfort Inn & Suites Winchester

Winchester

John

Rp1.675.721

Rp1.865.077 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A modern hotel dining area with a long table, multiple chairs, and a large window providing natural light.

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

4. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

Rp2.108.973

Rp2.347.287 total

includes taxes & fees

5 Oct - 6 Oct

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

A hotel room with two beds, a nightstand with a lamp, a desk with a chair, a window with curtains, and a wall-mounted air conditioner.

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".

5. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

CHRISTI

Rp1.430.629

Rp1.592.290 total

includes taxes & fees

11 Oct - 12 Oct

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

A hotel lobby with a wooden railing, a reception desk, a flower vase, and an exit sign.

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

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

6. Motel 6 Front Royal, VA

Front Royal

James

Rp1.163.516

Rp1.294.924 total

includes taxes & fees

4 Oct - 5 Oct

A swimming pool area with a fence, lounge chairs, and a flag.

A reception desk with a green wall, a plant, and various informational posters.

A building entrance with a neon 'OPEN' sign, a reception desk, and a clock.

A compact hotel room with a small round table, a coffee maker, a vase with flowers, a lamp, a framed picture on the wall, and a refrigerator.

7. Twi-Lite Inn

Front Royal

Victoria

Rp1.468.046

Rp1.634.007 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

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

Stephens City

Kevin

Rp1.611.270

Rp1.793.344 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

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

Winchester

Allen

Rp1.685.030

Rp1.875.438 total

includes taxes & fees

25 Oct - 26 Oct

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

A sign for a 'Relax Inn' with a clear view of the building in the background.

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

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

10. Relax Inn Motel

Front Royal

Jamila

Rp1.145.792

Rp1.275.231 total

includes taxes & fees

28 Sept - 29 Sept

A hotel room with two beds, a TV, a desk, and a dresser.

A room with a wooden floor, white walls, a wooden door, a table with chairs, a desk with a chair, a TV mounted on the wall, and a coat hanger in the closet.

A modern room with a wooden dresser, a mirror, a desk with a lamp, and a dining table.

An outdoor seating area with wooden chairs and a stone fire pit, surrounded by greenery and a mountain backdrop.

11. Hillside

Luray

Furkan

Rp2.124.549

Rp2.449.667 total

includes taxes & fees

28 Sept - 29 Sept

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 small, compact room with a kitchenette, a single bed, a television mounted on the wall, and a mirror above the bed.

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

12. Blue Ridge Motel

Front Royal

Karen

Rp1.047.326

Rp1.165.843 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

A hotel room with a red carpet, two white armchairs, a black sofa, a flat-screen TV, and two windows with blinds.

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

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

Front Royal

Snehil Meet

Rp1.306.919

Rp1.454.619 total

includes taxes & fees

28 Sept - 29 Sept

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

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.

A modern hotel lobby with seating areas, a reception desk, and large windows offering a view of the outdoors.

14. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

Rp2.488.517

Rp2.780.640 total

includes taxes & fees

13 Oct - 14 Oct

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

A hotel room with two beds, a desk, a television, a microwave, and a refrigerator.

A small stone building with a sign reading "Gateway Inn." It has a glass door entrance and a small awning.

A parking lot with several cars and motorcycles, a small building with a stone facade, and a clear blue sky.

15. Gateway Inn

Front Royal

Anonymous traveller

Rp1.056.277

Rp1.175.636 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A covered porch with wooden benches and potted plants, a tiled floor, and a view of a grassy yard.

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

16. L'Auberge Provencale Inn & Restaurant

Boyce

Henry

Rp4.656.570

Rp5.136.197 total

includes taxes & fees

28 Sept - 29 Sept

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

A reception area with a marble counter, a desk, and a framed picture on the wall.

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.

17. Quality Inn Stephens City - Winchester South

Stephens City

Nancy

Rp1.506.537

Rp1.676.775 total

includes taxes & fees

18 Oct - 19 Oct

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 multi-story hotel with a courtyard, outdoor seating, and a guest parking area.

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

18. Baymont by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Cindy

Rp1.141.316

Rp1.270.286 total

includes taxes & fees

4 Oct - 5 Oct

A dining area with a high ceiling, wooden beams, and a chandelier. There is a painting on the wall and an American flag. Tables and chairs are arranged for dining.

A hotel entrance with a covered walkway, a parking lot, and a building with a grey roof.

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

A Pepsi vending machine in a hallway with tiled flooring and a door in the background.

19. Econo Lodge Inn & Suites Middletown - Winchester South

Middletown

Nathan

Rp1.292.597

Rp1.425.616 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

20. Glen Gordon Manor

Huntly

Alexander and Judith

Rp7.143.297

Rp8.236.275 total

includes taxes & fees

1 Oct - 2 Oct

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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

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"We've stayed here several times and it has always been great. Bonus points for the attached Mexican restaurant and hot breakfast!"

Comfort Inn & Suites Winchester

10/10 Excellent

"Good"

Holiday Inn Express Winchester South-Stephens City by IHG

10/10 Excellent

"Good breakfast, comfy bed."

Hampton Inn Front Royal

10/10 Excellent

"Perfect, loved this hotel, bed are so comfortable, very clean. Staff was wonderful."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Good bed, nice size room, desk clerk was very helpful in getting us on the non-highway side of the property (which was then very quiet). Breakfast OK, lots of restaurants around the property and a movie theatre. Good location for Winchester"

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good

"Good place to stay...close to Shenandoah NP."

Twi-Lite Inn

10/10 Excellent

"ALL WAS WONDERFUL, THANK YOU"

Wayside Inn

10/10 Excellent

"We love staying at Wayside Inn. This is our third or fourth stay. The place is such a treasure! The food in the restaurant is good and the bar is fun. The only thing we noticed this time is that the bar closed at 9 p.m. on a Saturday night. We came in from dinner at 9:15 and planned to have a night cap and were told the bar closed at 9:00! The previous times we stayed there the bar was open until 10 or 11 on Saturday. We though such an early closing time was odd for the weekend."

Motel 6 Front Royal, VA

10/10 Excellent

"Older motel but there was effort to make it nice. there was a Koi pond out front and the fish were beautiful."

More cheap stays in Chester Gap

Baymont by Wyndham Front Royal Near Shenandoah National Park

10 S Commerce Ave Front Royal VA

Rp1.141.316

Rp1.270.286 total

4 Oct - 5 Oct

includes taxes & fees

Super 8 by Wyndham Front Royal Near Shenandoah National Park

111 South St Front Royal VA

Rp1.306.919

Rp1.454.619 total

28 Sept - 29 Sept

includes taxes & fees

7.6/10 Good! (1,003 reviews)

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

Rp1.430.629

Rp1.592.290 total

11 Oct - 12 Oct

includes taxes & fees

8.2/10 Very good! (1,009 reviews)

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

Rp1.675.721

Rp1.865.077 total

18 Oct - 19 Oct

includes taxes & fees

9.4/10 Exceptional! (1,137 reviews)

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Rp2.187.389

Rp2.434.564 total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (1,006 reviews)

Hillside

1460 US Highway 211 East Luray VA

Rp2.124.549

Rp2.449.667 total

28 Sept - 29 Sept

includes taxes & fees

9/10 Wonderful! (1,005 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 Dickey Ridge Visitor Center and Linden Vineyards 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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Book Hotels in Chester Gap on Expedia.com

Find hotels in Chester Gap, VA from Rp1.165.843

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. DoubleTree by Hilton Front Royal Blue Ridge Shadows

3. Comfort Inn & Suites Winchester

4. Fairfield Inn & Suites Strasburg Shenandoah Valley

5. Ramada by Wyndham Strasburg/Shenandoah Valley

6. Motel 6 Front Royal, VA

7. Twi-Lite Inn

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

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

10. Relax Inn Motel

11. Hillside

12. Blue Ridge Motel

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

14. TownePlace Suites by Marriott Front Royal

15. Gateway Inn

16. L'Auberge Provencale Inn & Restaurant

17. Quality Inn Stephens City - Winchester South

18. Baymont by Wyndham Front Royal Near Shenandoah National Park

19. Econo Lodge Inn & Suites Middletown - Winchester South

20. Glen Gordon Manor

Learn more about Chester Gap

Top Chester Gap Hotel Reviews

Ramada by Wyndham Strasburg/Shenandoah Valley

Comfort Inn & Suites Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Hampton Inn Front Royal

Country Inn & Suites by Radisson, Winchester, VA

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Twi-Lite Inn

Wayside Inn

Motel 6 Front Royal, VA

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

Hampton Inn Front Royal

Hillside

Frequently asked questions

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