Places to stay in Winchester

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Hidden Gem Everything, Everywhere!

This one of a kind home w/ newly appointed renovations & charming spaces will delight & enchant you! Set on 2 private acres, Paignton is in the middle of wherever you want to go. An enormous front porch & gazebo outside w/ lovely interiors within: living room & comfortable seating flat screen TV, elegant dining room, full kitchen & butlers pantry & 1/2 bath. A wide staircase takes you upstairs to a lovely seating area w/ 3 bedrooms (K,Q, 2T) w/ brand new, modern full baths & outdoor porch.

Hot Tub, Dog Friendly Boho Cabin in The Woods

Unwind at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, cuddle next to the wood burning fire, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a custom-built dog bowl station and two-acres for exploring. Just under two hours from the D.C./Baltimore area with a ChargePoint EV station in the driveway, it's the perfect all-seasons getaway for families and groups of friends.

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

Enlightenment, Mountain View

Enlightenment Mountain View Cabin Description Family reunion, friend reunion , 2 or 3 close dharma friends meditate , hiking , campfire ….. together Enjoy morning mist mountain view , amazing sunset ,the camp fire by your self and watch the the stars and the moon in the sky at night, the silent of the Mountain, fresh air, peaceful,private, quiet, country living, great place for meditation. , a Japanese style (Tatami) for meditation/tea room . Green ,wood ,flowers ,color leaves , snow ……

Amazing coffee bar! Lakeside, fishing, fire pit

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

Mountain Retreat with Large Hot Tub & Great WI-FI

Enjoy this beautiful and spacious, family oriented mountain cabin near Luray Caverns, with great views and 2,400 square feet of living space! The cabin has 3 bedrooms (1 king and 2 queen beds, 1 full hide-a-bed sofa) , Two and a half baths, and a LARGE HOT TUB, Pool Table, Firepit, TVs with Blu-ray players (42 inch upstairs, 65 inch smart TV downstairs), and excellent wifi. Book 7 nights and receive a 5% discount! ACTIVE DUTY DISCOUNT 5%!

Blue Mountain Hideaway- Unique Glamping Experience

Escape to our serene creek-side glamping retreat, where nature meets comfort. This private paradise offers hassle-free camping—just bring your cooler and clothes, we provide the rest! Relax by the creek, explore Shenandoah National Park, and enjoy cozy evenings around the campfire. With a comfortable bed, a fully equipped outdoor kitchen, and complementary firewood, your perfect escape awaits. Book your stay today!

Lux 5 Star HotTub, Deck, Mountain View, King Bed

This romantic and private house has large outdoor decks with hot tub and screened porch. The Area offers boating, fishing, hiking, zip lining, skiing, mountain biking, golfing, mini-golf, caving, wineries and just relaxing. Central AC, linens & towels provided, full kitchen. Great low weekday rates. Quite hours after 11:00 pm are strongly enforced by the local security and police.