Family-friendly vacation rentals in Sterling

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Top-rated family-friendly rentals in Sterling

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 567 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Sep 5 – 12

G$17,620 GYD per night

Guest favorite

Guest suite in Nokesville

4.97 out of 5 average rating, 431 reviews

Horse farm near Manassas Battlefield.

Comfortable accommodations for horses and the people traveling with them. Private suite, private entrance (bedroom, bath, kitchenette) + 2 RV hookups water/electric. 6 stalls - nice paddock turnout. Lighted arena. Close to: Manassas Battlefield (25 mile trail); Skymeadow State Park (nice trails); several hunt clubs; VRE connections - to METRO; 3 miles to Manassas airport. Not accepting pets for the time being. Several wineries and breweries within 12 miles - ONLY 6 miles to Jiffy Lube Live.

Jul 4 – 11

G$16,121 GYD per night

Guest favorite

Cabin in Haymarket

4.93 out of 5 average rating, 196 reviews

Lodge on the Lake

A cozy quiet 17 acre 1932 one room cabin set on a private small lake, great for fishing, swimming, and kayaking. Equipped with a full kitchen, a grill, 4 OUT DOOR showers, sleeps 4, 1 QUEEN SIZE BED AND 1 PULL OUT HIDE-A-BED. There is a $25/PP per day for extra guests , with prior approval by host. Pet friendly. Cameras are on site. 1 at the parking lot, 1 on the side deck, back deck, covered porch, up stairs open covered card/chest room, 2 on the main dock & water, 1 outside stone patio.

Nov 16 – 23

G$63,920 GYD per night

Guest favorite

Apartment in Reston

4.88 out of 5 average rating, 304 reviews

Studio Apt/Reston/by IAD&metro WIFI

Newly renovated downstairs studio apt. It is it's own apartment, but there is a shared laundry. 2.7 miles to Reston Town Center, Herndon, & the Reston metro. 15 minutes from Tyson's Corner and Dulles Airport. Washington, DC. Includes WIFI, washer/ dryer use, and Netflix. Private full bathroom. Private kitchen. The kitchen doesn’t have a stove. It has a microwave, plug-in burner, fridge and freezer, and a toaster oven that can fit a pizza. No guests are allowed that are not on reservation.

Jul 29 – Aug 5

G$22,997 GYD per night

Guest favorite

Cabin in Lovettsville

4.97 out of 5 average rating, 119 reviews

Rustic cabin + modern luxury in Lovettsville

Enjoy a one-of-a-kind stay in this restored 1800s cabin guest house with modern updates and beautiful decor. Off the beaten track but only about 1 hour from both DC and Baltimore. Located on a working farmstead and close to wine country, breweries, a goat cheese creamery, farm-to-table dining, and more. A favorite landing place for those out in the country enjoying Loudoun's Artists' Tour, Farm Tour, Wine Country Half Marathon, a wedding, a hiking trip, or just a weekend in the countryside.

Dec 26 – Jan 2

G$28,815 GYD per night

Guest favorite

Guest suite in Silver Spring

4.95 out of 5 average rating, 405 reviews

Private basement suite

Visit DC! Renovated basement w/ bedroom, en-suite bath, and kitchenette with private entrance available in residential Silver Spring. Home is one block to major bus lines, half a block to bike rental station, or 15 min walk/5 min bus ride to metro and is a quiet and safe but convenient location for your DC/ Silver Spring visit. UPDATE! Both metro stations near our home will be closed June- August 2024 due to purple line construction. Only bus service will be available for the summer.

Feb 19 – 26

G$15,640 GYD per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Jul 4 – 11

G$25,656 GYD per night

Guest favorite

Apartment in Leesburg

4.96 out of 5 average rating, 190 reviews

Heart of Loudoun Entire basement!

Guests love it here! Tucked away at the end of the lane yet right in the heart of Loudoun County. Private keyless entrance basement. Natural light filled fully equipped kitchen with full size appliances. King bed, full bath and a very spacious living room with 70" tv or movie screen...you choose! We have super fast Verizon Fios. Not your typical basement. Country living!!! There are many vineyards less than 10 minutes away and we are happy to make recommendations.

Aug 6 – 13

G$33,696 GYD per night

Guest favorite

Tiny home in Purcellville

4.96 out of 5 average rating, 313 reviews

Remote Tiny House in Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Aug 6 – 13

G$32,526 GYD per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 263 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Oct 2 – 9

G$25,001 GYD per night

Guest favorite

Tiny home in Bethesda

4.96 out of 5 average rating, 322 reviews

Middleton Cottage, near NIH; Free Parking Permit

Our newly updated charming guest cottage is nestled on a tree-lined residential street in the heart of Bethesda, just two blocks from the Bethesda Metro stop. A vast array of restaurants, clubs, shops, farmer's markets, bike trails, theaters, galleries, parks and more are a quick walk from our front gate. Guests enjoy relaxing in the backyard (which is shared with residents of the main house) and dinning on the patio. Self check-in is easy with a keypad.

Jan 9 – 16

G$23,924 GYD per night

Guest favorite

Apartment in Reston

4.97 out of 5 average rating, 204 reviews

Great Location w/ Cozy Atmosphere

Our quaint apt is perfectly located minutes from Dulles Airport, Metro, DC, restaurants, shopping centers & entertainment options. A finely decorated apartment providing all the essentials you'll need for your stay. We hope you like what you see! .... We are currently taking the proper precautions to make sure everything in the apt. is thoroughly cleaned and disinfected after each guest so you can feel safe.

Dec 28 – Jan 4

G$30,572 GYD per night