Family-friendly vacation rentals in Winchester

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cabin in Massanutten Resort

4.93 out of 5 average rating, 122 reviews

Log Cabin Lodge That Has It All

This spacious lodge in Massanutten Resort features cathedral ceilings, lots of natural light, and a stone fireplace. The upper-level game room features a ping pong table, corn hole, wide-screen TV and more. There's also a cozy loft space! Enjoy the serenity of the large lot with porch swings, a seasonal creek, and walking paths adjoining the forest. The deck features a hot tub, hammock, casual seating, outdoor dining space, herb garden, and a BBQ grill. Minutes from the resort amenities.

Guest favorite

Cabin in Shenandoah

4.93 out of 5 average rating, 231 reviews

35 Acres, Additional River Lot, Hot Tub, Pets OK

Shenandoah River waterfront lot included with rental. House is NOT waterfront. Lot is 1 mile drive from driveway entrance. The cabin is nestled in a hollow on 35 acres of private mountainside. Following the winding driveway through a railroad tunnel you reach Fox Creek Lodge. 15mi to Massanutten Ski & Water Park, Luray Caverns and 17mi to Shenandoah National Park/Skyline Drive. Many wineries & breweries and outdoor activity companies to help with river tubing, canoeing, fishing and hot tub.

Guest favorite

Cabin in Stanley

4.98 out of 5 average rating, 168 reviews

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!

Superhost

Cabin in Shenandoah

4.97 out of 5 average rating, 158 reviews

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.

Guest favorite

Chalet in Basye

4.78 out of 5 average rating, 175 reviews

"The Duke Den"

Chalet home near Bryce Resort. Three bedroom, three bathroom. Kitchen, microwave, dishwasher, gas and charcoal grills. TV in master bedroom, in main floor living area and in rec room. Cable TV, WiFi, DVD player w/section of movies, board games and books for winding down after a day of activities at the resort. Short drive to Bryce Resort and Lake Laura. Bryce is a four-seasons resort. Enjoy swimming, tennis, fishing, mountain biking, zip lining, golf in summer, ski in winter.

Superhost

Townhouse in Woodbridge

4.85 out of 5 average rating, 104 reviews

Bright Three Level Lake Ridge Townhome Close to DC

Cozy three level townhome with three bedrooms including 2 full & 1 half baths between Washington DC and Quantico, a 20-30 minute drive to Ft. Belvoir, 15 minutes from the VRE/Amtrak station and 10 minutes from I95. Nice main level deck that backs up to a wooded area. Close to shopping mall, grocery stores and restaurants. Washer and dryer included. The couch in the living room is not a sleep sofa but can be used to sleep on. Two parking spaces available in front of the home.

Superhost

Home in Rockingham

4.78 out of 5 average rating, 256 reviews

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

Superhost

Cabin in Harpers Ferry

4.8 out of 5 average rating, 416 reviews

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!

Guest favorite

Farm stay in Ijamsville

4.96 out of 5 average rating, 281 reviews

Historic Farm Stay with Modern Amenities

Escape to our historic farm stay, where charm meets modern comfort. Enjoy the gourmet kitchen, unwind on the magnificent patio with a huge fire pit, and indulge in the infrared sauna. Perfect for families and friends, with an adorable kid's playhouse and games. Interact with friendly animals, immerse yourself in serenity, and experience the ultimate getaway near Whiskey Creek Golf Course in Ijamsville. Contact Fingerboard Farm directly for larger gatherings.

Guest favorite

Guesthouse in Frederick

4.98 out of 5 average rating, 173 reviews

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.

Guest favorite

Home in Harpers Ferry

4.94 out of 5 average rating, 383 reviews

Gayte House Gay Owned, Liberal Oasis

Cozy and charming 1840's home in the heart of town. Steps from the National Park, feet from the Appalachian Trail. Relax by the fire, on the porch or on the river. We have something for every season and every age. Steve and I have lived here In HF 20 yrs., 13 of those at the Gaytehouse. We live right next door now and Love both our homes. Please, Check out the beautiful and cherished home we offer for your stay.

Guest favorite

Chalet in Brightwood

4.97 out of 5 average rating, 129 reviews

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