
Hotels in Winchester
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Top-rated hotels in Winchester
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Prime Spot! Pet-friendly Property, Free Breakfast!
See a vacation through the eyes of one of our visitors! The National Firearms Museum and Fair Oaks Park are just a few of the city's many cultural attractions. Learn the true meaning of travel and how much fun you can have by staying at this first-rate hotel. The location of the property puts public parks and shopping malls within easy walking distance. It offers a variety of recreational activities, including golf and wine tasting. By living here, you experience the wonders of this amazing city

A Great Stay in Chambersburg with beautiful rooms!
You’ll love the stylish decor of this charming place to stay. Inviting hotel off I-81 close to historic Gettysburg Our welcoming Baymont by Wyndham Chambersburg hotel is situated in the Cumberland Valley, just 15 miles from the Pennsylvania-Maryland border. We’re located off I-81 at exit 14 and Wayne Ave., 25 miles west of historic Gettysburg and close to many restaurants and Amish farm markets. Lots of great local attractions too! Please contact the hotel for information on extended stay rates.

The Knolls Town & Country Room 9
This vintage motel has been updated to provide charming efficiency rooms. Each room has a kitchenette, private bath, 55” smart tv, & Wi-Fi. The Knolls is located steps from the VA, minutes from Martinsburg & Charles Town, & close to Charles Town Casino as well as many other local attractions. Parking is directly in front of your door. Each room is equipped with a smart lock on the door. Room #9 is comfortably designed with luxury linens, memory foam mattress, and so much more. Come stay with us!

The Ridge 03 Visit Harrisonburg-King bed
Centrally located in the heart of the Friendly City, this stylish rental is minutes from the lively downtown of Harrisonburg. Perfect for a weekend of exploring the Valley or visiting JMU, it provides comfortable, clean, and newly remodeled rooms. Rooms are located in a central building that includes shared hallway, laundry, common area with microwave, coffee station (supplies included) and outdoor seating area with fire ring. Downtown sport delicious cuisine for your enjoyment.

Close to Quantico Marine Corps Base
A quite, secure setting just outside the Marine Corp Base Quantico and the Marine Corp National Museum. Only 35 miles to Washington DC and close to historic Fredericksburg VA. This one bedroom unit has a fully equipped kitchen and flat screen TVs in the living room and the bedroom. Pets (dogs only) are allowed with a fee. Please contact host for details on pet policies and fees.

Prime Downtown Location+Celebrity Chef Restaurant
The Visitation Hotel Frederick offers an upscale, boutique experience, blending historic elegance with modern comforts. This landmark building, with a rich 200-year history, has been transformed into a premier hotel. Originally a monastery and later a well-known school, the Visitation Hotel now welcomes travelers seeking a peaceful and comfortable stay.

Historic Hotel Gunter - Room 312
Step into the timeless elegance of the Hotel Gunter, the iconic five-story landmark that has graced Downtown Frostburg since 1897. Adorned with classic balconies, it remains a beloved gathering place. Nestled in the heart of the town, our historic hotel offers modern comfort alongside effortless access to the finest local shops and restaurants.

Wayside Inn (Room #18 ) Shenandoah Guest
Room 18 - The Shenandoah Guest Room has a queen bed and a bath with a shower only (no tub). The Shenandoah Guest Room is in the South wing on the 1st floor. This guest room was named for the Shenandoah Valley. The history of Wayside Inn is very important to the Shenandoah Valley. Check-in begins at 3 pm, check-out time is at 11 am.

The Hermitage Inn Full 1 Bed
Experience the charm of history while enjoying modern comforts in our beautifully restored historical suite located in the heart of Grant County. Includes a cozy full-size bed with premium linens for a restful night's sleep. Equipped with essential appliances and dining essentials for a home-away-from-home experience.

Easy access to DC & just 10 mins from the airport
The Aloft Guestroom at Aloft Dulles Airport North features a stylish 285 sq ft (26 sqm) layout equipped with a mini fridge and coffee/tea maker. Enjoy Aloft’s contemporary design, plus wireless internet access (for a fee), making this room a comfortable and convenient choice for any traveler.

Single (1 Full Bed)
One double bed with a microwave & mini fridge. The room has been updated with flat screen televisions, mini-fridges, microwaves, air-conditioning, and free wi-fi. Many of the rooms have been remodeled to update flooring, plumbing, electrical, and bathroom fixtures.

George Washington l Queen Bed l Historic Charm
Stay in the heart of Winchester’s walkable downtown, where fine dining and local history meet. This well-appointed queen room offers upscale finishes, elegant décor, and all the essentials for a restful night. A perfect fit for solo travelers or couples.
Popular amenities for Winchester hotels
Family-friendly hotels

Wayside Inn (Room #4) Wilkenson Guest Room

Wayside Inn (Room #8) Taylor Guest Room

Wayside Inn (Room #17) Lee Guest Room

Wayside Inn (Room #21) Hite Guest Room

Wayside Inn (Room #15) Bernstein Suite

Wayside Inn (Room #6) Lincoln Stateroom

Wayside Inn (Room #1) Jubal Early State Room

Minutes to D.C. | Indoor Pool. Gym. On‑Site Dining
Hotels with a pool

Modern Hotel with Small Town Charm

Luxury 2 Bed & 2 Bath Unit with Full Amenities

Deluxe King | Wingate Chantilly | Free Breakfast

Signature Aloft chill vibe and grab-n-go eats

2 Queen Beds | Wingate Chantilly | Park & Fly

Serene Hideaway Perfect for a Relaxing Countryside

House shuttle zips you to/from the airport gratis

Suite In Manassas
Hotels with a patio

The Ridge 01 Explore Shenandoah-JMU-Queen bed

The Ridge 11 Travel JMU Harrisonburg- Queen bed

The Ridge 06 JMU/Business Travel - Queen

The Ridge 12 Travel JMU Harrisonburg - Queen Bed

The Ridge 08 - Explore Harrisonburg/JMU

The Ridge 07 JMU Queen Bed

The Ridge 10 Visit Harrisonburg JMU -King Bed

The Ridge 13 Visit Harrisonburg
Quick stats about hotels in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $167 CAD per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Winchester vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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- Hotel rooms Virginia
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- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Whitetail Resort
- South Mountain State Park
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- Big Cork Vineyards
- Green Ridge State Forest
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- Shenandoah River Outfitters
- Antietam National Battlefield
- Rock Gap State Park
- Cooter's Place
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- Reston Town Center
- Skyline Caverns
- Museum of the Shenandoah Valley
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- Hollywood Casino At Charles Town Races
- Old Town Winchester Walking Mall




