Family-friendly holiday rentals in Winchester

Stunning Mountain Views in Luxurious Log Home!

Perfect for couples or families wanting STUNNING MOUNTAIN VIEWS (from the cabin & from the hot tub) in the ideal location. Romantic, luxurious & immaculately clean custom cabin, fully equipped w/all pine interior. Super close to Shen Natl Park/Skyline Drive, Luray Caverns, unique shops & markets, restaurants, horseback riding, fishing, golf, wineries/breweries, historic sites, Shenandoah River, Lake Arrowhead & the slopes of Massanutten Resort! Find us at LURAY MOUNTAIN CABINS for SPECIALS!

Cuddly Cub Cabin

Cuddly cub cabin will sleep 6-8 guests, and is close to National Parks, Luray Caverns and the Shenandoah River. You’ll love cuddly cub cabin because of the hot tub, the screened in porch, the fire pit, the BBQ area and the indoor surround sound system . Cuddly Cub is perfect for couples, solo adventurers, business travelers, families (with kids), and furry friends (dogs only). 2 night minimum booking on weekends - single night stays welcome during the week. Holidays require 3 night booking.

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

Stone Spring - Heated Salt Pool - on 2.5 Acres

Heated Salt water pool and hot tub on 2.5 Acres. Lawn games & outdoor living room! New for '21 - Stove, Upstairs Flooring, Foosball Table, Board Games, paint New for '20 - Antimicrobial door handles, kitchen items Completely separate owner/caretakers quarters onsite, occupied by our property manager. Pool, hot-tub, grilling, etc are private spaces for guests and NOT shared *entrance and egress through pool area* *playhouse removed, gas fireplaces inoperable *no pets

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Romantic Getaway - Heated Spa Open Year Round

Enjoy our beautifully decorated four bedroom home, furnished with unparalleled elegance and style. This tranquil guest house is located less than an hour from Washington DC and Baltimore, MD, and a half-hour from Gettysburg and Harper's Ferry and offers luxurious rooms with unparalleled elegance and style. For the ultimate pampered experienced, guests can arrange for in-house spa services such as a full-body therapeutic massage.

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet

Massanutten Woodstone 2-BR, 2 Bath

I can offer you reduced prices on a week or two of vacation in a luxurious and spacious GOLD CROWN unit in a four seasons resort. All units have been recently remodeled in 2020, 2021 or 2022. You can expect a clean room that includes all the things you need in the kitchen and bathrooms. The resort has a mandatory $15.50 daily resort fee per unit payable upon check-in.

Tree top home in Massanutten next to tubing

This updated 3 bedroom, 2 bathroom private villa is situated beside the slopes, on-property in the heart of Massanutten Resort! Enjoy the updated ambiance, vaulted ceilings, private back deck, wood burning fireplace, fire-pit and more. Perfect get away anytime of the year!