
Hotels in Winchester
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Top-rated hotels in Winchester
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Look No Further! Free Breakfast, Pets Allowed
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 Ridge 07 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.

Close to Wineries + Sauna & On Site Dining
Step into the charm of downtown Leesburg at Hotel Burg, a boutique stay on South King Street surrounded by wine bars, local dining, and historic streets. Walk about 0.1 miles (~2 min) to shops and cafés, or head into Loudoun County wine country just minutes away. Washington Dulles International Airport is approx. 13 miles (~20 min drive). Guests love rooftop drinks, The Huntōn restaurant, a fitness center with infrared sauna, and pet-friendly stays with no added fee.

Botanical
You will enjoy your stay at this remodeled vintage motel. Each room boasts queen bed, 55" smart tv, Wi-Fi, kitchenette, private bath, luxurious linens, & front door parking. This prime location is steps from the VA Hospital, minutes from Martinsburg, Charles Town, & Harpers Ferry and a short driving distance to many historical & local attractions. Every room is uniquely decorated with comfort in mind.

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 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.

Spacious Room Short Drive to EagleBank Arena
Enjoy a relaxing stay in Fairfax, VA, near George Mason University and Fair Oaks Mall. Ideal for both business and leisure, with spacious, pet-friendly rooms and Southern-inspired dining. Explore local attractions like Patriot Park North and EagleBank Arena. With great service and modern amenities, your visit will be comfortable and memorable.

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.

APM Inn & Suites
Feel at home with our comfy, cozy rooms! Our indoor pool has been renovated and is up running. We are pet friendly, additional fees apply upon check-in. Our hotel is a close distance to Historical Downtown Winchester and short distance to many food places.
Popular amenities for Winchester hotels
Family-friendly hotels

The Hermitage Inn Full 1 Bed

Close to Potomac Mills Mall + Breakfast & Kitchen

Historic Leesburg Stay w/ Bunkbeds + Sauna

A Great Stay in Chambersburg with beautiful rooms!

Winchester Stay | 2 Units | Downtown Location

Minutes to D.C. | Indoor Pool. Gym. On‑Site Dining

Comfortable Stay at Super 8 Dumfries

Renovated Hotel By Historic Park
Hotels with a pool

King Room l George Washington l Double Vanity

King Room l George Washington l Downtown Charm

2 Units | Queen Room | George Washington

Modern Hotel with Small Town Charm

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
Hotels with a patio

Woodstone Massanutten 4 Bedrooms

Historic Hotel Gunter - Room 308

Historic Hotel Gunter - Room 309

Historic Hotel Gunter - Room 303

Historic Hotel Gunter - Room 311

Historic Hotel Gunter - Room 310

Historic Hotel Gunter - Room 314

Historic Hotel Gunter - Room 315
Quick stats about hotels in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at ﺩ.ﺇ220 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

Wi-Fi availability
20 of Winchester vacation rentals include wi-fi access

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