
Hotels in Winchester
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Top-rated hotels in Winchester
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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!

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 12 Travel JMU Harrisonburg - 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.

Boutique Motel in Fairfield
Kick back and relax, Stay a little longer at Fairfield Extended Stay. These rooms are designed with the furnishings of a well-appointed home, featuring mini fridge and microwave, full baths, and a comfortable living area. Our extended stay motel near Fairfield, PA is ideal for corporate relocation, extended work engagements, vacationing in Gettysburg and other short or long term lodging needs. this calm, stylish space.

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.

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.

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.

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 #11) Tyler Guest Room

Wayside Inn (Room #17) Lee Guest Room

Wayside Inn (Room #6) Lincoln Stateroom

Wayside Inn (Room #15) Bernstein Suite

Wayside Inn (Room #1) Jubal Early State Room

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

Wayside Inn (Room #3) Cedar Creek Guest Room
Hotels with a pool

King Room l George Washington l Double Vanity

Luxury 2 Bed & 2 Bath Unit with Full Amenities

Deluxe King | Wingate Chantilly | Free Breakfast

Signature Aloft chill vibe and grab-n-go eats

George Washington l King Room l Historic Hotel

2 Queen Beds | Wingate Chantilly | Park & Fly

Winchester Stay | 2 Units | Downtown Location

House shuttle zips you to/from the airport gratis
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 08 Sweet Hearts Getaway!

The Ridge 03 Visit Harrisonburg-King bed

The Ridge 07 JMU Queen Bed

The Ridge 05 Explore Valentine's Day Retreat

The Ridge 10 Visit Harrisonburg JMU -King Bed
Quick stats about hotels in Winchester

Total holiday rentals
Explore 20 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $151 SGD per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Winchester holiday 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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- Family-friendly rentals Winchester
- Rentals with breakfast Winchester
- Cottage rentals Winchester
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- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with pools Winchester
- Flat rentals Winchester
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- Rentals with a fireplace Winchester
- Hotel rooms Virginia
- Hotel rooms United States
- Whitetail Resort
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Gambrill State Park
- South Mountain State Park
- Harpers Ferry National Historical Park
- Shenandoah River Outfitters
- Sky Meadows State Park
- Jiffy Lube Live
- Big Cork Vineyards
- Cooter's Place
- Green Ridge State Forest
- Antietam National Battlefield
- Reston Town Center
- Rock Gap State Park
- Museum of the Shenandoah Valley
- Old Town Winchester Walking Mall
- Bluemont Vineyard
- Catoctin Mountain Park
- Greenbrier State Park




