
Hotels in Winchester
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Quick stats about hotels in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 110 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

4.5 Average rating
Winchester stays receive an average rating of 4.5 out of 5 from guests
Top-rated hotels in Winchester
Guests agree: these hotels are highly rated for location, cleanliness, and more.

Get an Overall Fantastic Stay! 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

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 15 Harrisonburg JMU - Queen 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.

Door-to-door shuttle service to/from Dulles
Hyatt Regency Dulles features 316 spacious rooms and suites designed for you to relax and stay productive. Our fresh, contemporary style blends perfectly with our premium travel amenities, including plush beds, 55" HDTV, Pharmacopia bath amenities, free Wi-Fi and oversize work desk. Upgrade to one of our suites and enjoy extra perks like separate bedroom and living areas, conference table, second TV and beautiful views.

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.

Deluxe King | Wingate Chantilly | Free Breakfast
Located near Washington Dulles International Airport, Wingate by Wyndham Chantilly offers modern comfort and is close to top attractions, including the Steven F. Udvar-Hazy Center. This deluxe king room features upgraded touches for a relaxing stay. Guests can start their mornings with a hearty complimentary breakfast before catching their flight or exploring nearby sites.

Historic Hotel Gunter - Room 316
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.

2 Queen | Wyndham Manassas | Near Jeff Lube Live
A comfortable Manassas stay with quick access to Northern Virginia favorites. Spend the day at Manassas National Battlefield Park, browse Historic Old Town Manassas, or plan a concert night at Jiffy Lube Live. Between plans, reset with the indoor saltwater pool and seasonal outdoor pool, plus a fitness center to keep your routine steady.

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.

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

The Ridge 11 Travel JMU Harrisonburg- Queen bed

Historic Hotel Gunter - Room 303

Wayside Inn (Room # 19) Massanutten Guest Room

Historic Leesburg Stay w/ Bunkbeds + Sauna

A Great Stay in Chambersburg with beautiful rooms!

Massanutten's Woodstone Resort - 1 bedroom

Botanical

Shepherdstown
Hotels with a pool

2 Units | Queen Room | George Washington

2 Queen Beds | Wingate Chantilly | Park & Fly

Serene Hideaway Perfect for a Relaxing Countryside

Wingate Chantilly | King Bed | Near Dulles

La Quinta Winchester | King | Near I-81

Suite In Manassas

George Washington l King Bed l Vanity for Two

George Washington l Double Room l Great for 4
Hotels with a patio

The Ridge 01 Explore Shenandoah-JMU-Queen bed

Historic Hotel Gunter - Room 309

The Ridge 06 JMU/Business Travel - Queen

The Ridge 12 Travel JMU Harrisonburg - Queen Bed

Historic Hotel Gunter - Room 311

The Ridge 08 - Explore Harrisonburg/JMU

The Ridge 03 Visit Harrisonburg-King bed

Historic Hotel Gunter - Room 315
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- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Jiffy Lube Live
- Berkeley Springs State Park
- Harpers Ferry National Historical Park
- Cunningham Falls State Park
- Rock Gap State Park
- Cacapon Resort State Park
- South Mountain State Park
- Whitetail Resort
- Shenandoah River Outfitters
- Greenbrier State Park
- Reston Town Center
- Sky Meadows State Park
- Hollywood Casino At Charles Town Races
- Green Ridge State Forest
- Bluemont Vineyard
- Antietam National Battlefield
- Weinberg Center for the Arts
- Gambrill State Park
- Dulles Town Center
- Skyline Caverns
- Big Cork Vineyards




