Photo by Brian V. Rowe

Chester Gap Hotels from S$76

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Top 10 trending Chester Gap hotels

Comfort Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1006)
"Convenient to shopping and restaurants."
The price is S$136
includes taxes & fees
12 Jun - 13 Jun
Comfort Inn & Suites

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (164)
"I had the most amazing time here. All i wanted.... place is beautiful & peaceful. "
The price is S$326
includes taxes & fees
2 Jul - 3 Jul
L'Auberge Provencale Inn & Restaurant

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (136)
"Perfect location and stay to combine with dinner at the Inn at Little Washington."
White Moose Inn

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (86)
"Very nice one night stay on a historic property. Very nice common areas. Very relaxing. Good service. Nice breakfast."
The price is S$351
includes taxes & fees
9 Jul - 10 Jul
Glen Gordon Manor

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (32)
"Great place to stay in Washington VA to walk to inn at little Washington, patty O's (6 min walk), bakery, chocolates and rural landscape! "
The price is S$499
includes taxes & fees
26 Jun - 27 Jun
Gay Street Inn

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Stayed here for my spring trip to Shenandoah National Park, and had a perfect time. The hotel had everything I needed and the hot tub/pool were excellent. "
The price is S$172
includes taxes & fees
15 Jun - 16 Jun
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (393)
"It was quaint and interesting, but beware if you don’t like the smell of antiques. I had to track down staff to check in and call the manager who frankly seemed a bit miffed that I called her. Staff member was friendly upon arrival. Water pressure in the shower was not great, although the room was clean."
The price is S$150
includes taxes & fees
10 Jun - 11 Jun
Wayside Inn

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.6 out of 10, Excellent, (1006)
"Great stay for a great price!"
The price is S$130
includes taxes & fees
12 Jun - 13 Jun
Country Inn & Suites by Radisson, Winchester, VA

Hampton Inn Front Royal

2.5 star property
8.8 out of 10, Excellent, (1002)
"Recently renovated..very friendly staff"
The price is S$151
includes taxes & fees
10 Jul - 11 Jul
Hampton Inn Front Royal

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
9.8 out of 10, Exceptional, (30)
"Great place. Good food, great beer."
Hopkins Ordinary Bed Breakfast and Ale Works

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Great place to stay in Strasburg Va"
The price is S$157
includes taxes & fees
22 Jun - 23 Jun
Fairfield Inn & Suites Strasburg Shenandoah Valley

Hillside

2.5 star property
9.0 out of 10, Wonderful, (938)
"Good, clean motel, and lovely staff"
The price is S$172
includes taxes & fees
9 Jul - 10 Jul
Hillside

TownePlace Suites by Marriott Front Royal

3.0 star property
9.6 out of 10, Exceptional, (499)
"Very nice place to stay."
The price is S$180
includes taxes & fees
30 Jun - 1 Jul
TownePlace Suites by Marriott Front Royal

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (748)
"Easy and cheerful check in. Property is very clean. Beds are comfortable. Nice breakfast"
The price is S$130
includes taxes & fees
15 Jun - 16 Jun
Holiday Inn Express Winchester South-Stephens City by IHG

Twi-Lite Inn

2.0 star property
8.2 out of 10, Very good, (508)
"nice place"
The price is S$115
includes taxes & fees
11 Jun - 12 Jun
Twi-Lite Inn

Relax Inn Motel

2.0 star property
8.2 out of 10, Very good, (233)
"Clean, quiet and convenient. Check in process was quick and easy, with the very friendly and helpful staff. I would absolutely stay here again."
The price is S$99
includes taxes & fees
10 Jun - 11 Jun
Relax Inn Motel

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.0 out of 10, Very good, (1003)
"Friendly staff..clean rooms, quiet setting, good breakfasts"
The price is S$102
includes taxes & fees
15 Jun - 16 Jun
Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very good, (573)
"Very efficient.checkin."
The price is S$106
includes taxes & fees
1 Jul - 2 Jul
Quality Inn Stephens City - Winchester South

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1002)
"Great place"
The price is S$106
includes taxes & fees
16 Jun - 17 Jun
Super 8 by Wyndham Front Royal

Blue Ridge Motel

2.0 star property
7.2 out of 10, Good, (126)
"Inexpensive for a 1 night stopover. Dated rooms and limited facilities . Comfy sleep though"
Blue Ridge Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

More cheap stays in Chester Gap

More cheap stays in Chester Gap

Recent Reviews in Chester Gap

Recent Reviews in Chester Gap

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Frequently asked questions

Where is the best place to stay in Chester Gap?

Ramada by Wyndham Strasburg/Shenandoah Valley, located 15.2 mi (24.5 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 and Country Inn & Suites by Radisson, Winchester, VA. 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 are some hotels with pools in Chester Gap?

The Hillside Motel: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Winchester, VA and Hampton Inn Front Royal are two additional hotels that feature an on-site pool. View all hotels with pools in Chester Gap.

What is the best spa hotel 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 4 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.