Family-friendly vacation rentals in Montgomery Village

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Top-rated family-friendly rentals in Montgomery Village

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

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Guest favorite

Apartment in Silver Spring

4.93 out of 5 average rating, 395 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Living Room amenities include a Smart TV and an Amazon Fire TV Stick. Fully equipped kitchen and cooking essentials. Lovely patio with seating area and herb garden. Comfortable bed and quality linens. Keurig coffee maker with coffee and tea provided. You have your own private entrance and patio area on an entire different side of the house so your experience can be as private as you like. The entire apartment which includes: washer/dryer, fully equipped kitchen and patio area. Your host will be available for anything you need during your stay. My daughter/co-host, Bernadette, a young D.C. professional, can also answer any questions about the D.C. area, restaurants and other cool places to go. The apartment is in a quiet suburban neighborhood with easy access to the Washington area. It's a short walk to the FDA. Downtown Silver Spring is nearby, with its many restaurants, bars, Fillmore music venue, Ellsworth Dog Park, and a movie theater. The National Archives, University of Maryland College Park and UMUC are just few miles away. A Ride-On bus stop is located on the same block as the apartment. A Metro bus stop is 5 minute walk. Silver Spring Metro Station is about 4 miles away. There are a few parking garages at the Silver Spring Metro Station if you choose to drive there and then hop on the metro. Free parking on weekends and holidays at all Montgomery County Parking garages (some lots and street parking may require payment on Saturday). You could also Uber/Lyft to the metro station or all the way into the city (great option esp if you're splitting fare).

Oct 5 – 12

R1,802 ZAR per night

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.

Aug 15 – 22

R1,618 ZAR per night

Guest favorite

Guesthouse in Glenwood

4.94 out of 5 average rating, 160 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Sep 13 – 20

R3,487 ZAR per night

Guest favorite

Guest suite in Laurel

4.98 out of 5 average rating, 172 reviews

Whiskey Bottom Saloon by LLOYD SUITES

Whether you're a service member transferring to the area or here for business or pleasure, our 'Saloon' themed apartment is the perfect retreat. We're 25 mins from DC and 20 mins from Baltimore. Just a gallop to I-295, I-95 and Fort-Meade. Are you flying in from BWI Airport? We are only 15 mins away. If you would like to try your luck, we are 20 mins from Maryland LIVE Casino and Horseshoe Casino. Within walking distance is the famous Laurel Park Horse Race Track with live & simulcast races.

Jul 18 – 25

R2,222 ZAR 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 16 – 23

R1,481 ZAR per night

Guest favorite

Guesthouse in Middletown

4.95 out of 5 average rating, 246 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Sep 13 – 20

R2,035 ZAR 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.

Jan 25 – Feb 1

R2,611 ZAR 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.

Aug 22 – 29

R1,437 ZAR per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 643 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Feb 3 – 10

R1,796 ZAR 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

R2,296 ZAR 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.

Aug 21 – 28

R2,200 ZAR per night

Superhost

Guest suite in Highland

4.78 out of 5 average rating, 101 reviews

The whole first floor is yours in MD Columbia

Welcome to the American Dream! Our home(total 6000+ square feet) is set in a picturesque suburban neighborhood of the nation's capital. On our first floor, we have spacious two bedrooms ,two bathrooms , a private access, and a full complement of amenities just for you! we can have 6 quests in total! Our 1.6 acre yard is perfect for anything from a peaceful lounge to a pickup soccer game. If you have a family, welcome!

Jul 8 – 15

R1,983 ZAR per night