
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 G$12,555 GYD 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
Top-rated hotels in Winchester
Guests agree: these hotels are highly rated for location, cleanliness, and more.

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 09 JMU /Business Travel - King
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.

Wayside Inn (Room # 19) Massanutten Guest Room
Room 19 ~ The Massanutten Guest Room has a double bed and a full bath with a standard tub. This origin of the name for this room has a couple of versions. One is that it was named by the local Native Americans. "Massa" which means ground and "Nutten" means potato. Another version is that the Native Americans named it the Great Lookout Mountain. This room is one of three rooms on the first floor in the south wing. Check-in time begins at 3 pm, check-out time is at 11 am.

Minutes to D.C. | Indoor Pool. Gym. On‑Site Dining
Enjoy a modern, convenient stay at Courtyard Potomac Mills Woodbridge, ideally located just off I-95 and minutes from Potomac Mills Outlet Mall. Perfect for business, weekend getaways, or family trips, the hotel offers newly updated rooms with plush bedding, HDTVs, and workspaces, plus great amenities like an indoor pool, restaurant, and 24-hour fitness center. Only 25 miles south of Washington, D.C., you’ll be close to shopping, dining, and top regional attractions.

Near Rockville's Tech Corridor + Gym. Pool. Dining
Check in, drop your bags, and explore Rio Lakefront or grab dinner near the water. At Hilton Garden Inn Rockville-Gaithersburg, you’re minutes from Rockville’s Tech Corridor, local trails, and Shady Grove Metro—but still tucked into a quiet spot with a pool, gym, and on-site bar. Fast Wi-Fi, and comfy rooms make it easy to unwind, whether you're visiting campus, exploring D.C., or working in the heart of Montgomery County’s innovation hub.

Near Potomac Mills Mall + Breakfast. Kitchen. Pool
Stay close to Potomac Mills Mall and just minutes from Quantico at Residence Inn Woodbridge Potomac Mills. Perfect for families, groups, and business travelers, every spacious suite includes a full kitchen, free Wi-Fi, and separate spaces to work and relax. Fuel up with free hot breakfast, swim year-round in the indoor pool, and stay on track with the fitness center. Paid on-site parking and a prime I-95 location make getting around easy.

Queen Studio w/ Kitchen + Free Breakfast & Pool
Welcome to Residence Inn by Marriott Gaithersburg Washingtonian Center, your extended-stay home in the heart of one of Gaithersburg’s most vibrant neighborhoods. Wake up to free hot breakfast daily, relax by the seasonal outdoor pool, and explore Rio Lakefront just steps away. Whether you're here for work or play, our spacious suites with full kitchens and thoughtful amenities are designed to make every stay effortless.

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.

Seneca Pines Lodge - King Suite
Welcome to your retreat at Seneca Pines Lodge! Our newly renovated king bedroom features a luxurious Dreamcloud mattress, a 55” Roku TV, and a convenient kitchenette. Unwind in the large glass and tile shower and stay connected with free WiFi. Located just 5 minutes from the Seneca Rocks trailhead, our lodge is perfect for adventurers. Plus, we’re pet-friendly. Book now for a relaxing and memorable stay!

Near Wolf Trap National Park + Breakfast. Pool.
Spread out, sleep in, and sip free cocktails at this two-room suite stay near Tysons Corner. Wake up to made-to-order breakfast (hello, omelets), hop on the Metro to explore D.C., or chill by the indoor pool after a day of shopping or sightseeing. With on-site parking, and a separate living room in every suite, it’s the perfect mix of hotel perks and homey space—no tiny rooms or shared kitchens here.

C50L - King, Queen, Bunkbed, Loft, Dog Friendly
What guests love about these units is having a large, two bathroom 768 SF unit on two floors with a kitchenette, a living room sitting area with it’s own flat screen TV over the cozy fireplace. Note, you may hear your neighbors next door when in a duplex cabin. The loft in this cabin features a queen bed, bunk bed and a full bathroom. Also has a sleeper sofa.
Popular amenities for Winchester hotels
Family-friendly hotels

Single (1 Full Bed)

Upscale Extended Stay Suite Hotel W/Free Breakfast

Botanical

Shepherdstown

The Knolls Serenity Room 7

Close to Quantico Marine Corps Base

Meeting House | Queen

Look No Further! Free Breakfast, Pets Allowed
Hotels with a pool

Ski-in/Ski-out | Four seasons Wisp Resort

Close to Potomac Mills Mall + Breakfast & Kitchen

Deluxe King | Wingate Chantilly | Free Breakfast

2 Queen Beds | Wingate Chantilly | Park & Fly

Serene Hideaway Perfect for a Relaxing Countryside

Wingate Chantilly | King Bed | Near Dulles

Suite In Manassas

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

Woodstone Massanutten 4 Bedrooms

Historic Hotel Gunter - Room 309

The Ridge 06 JMU/Business Travel - Queen

Renovated Hotel By Historic Park

Historic Hotel Gunter - Room 312

The Ridge 03 Visit Harrisonburg-King bed

Historic Hotel Gunter - Room 307

Getaway in Virginia for 6!
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