Family-friendly holiday rentals in Montgomery Village

4.94 out of 5 average rating, 120 reviews

The exterior of a spacious two-story house is presented, featuring a light brown façade, large windows, and decorative window shutters. A welcoming front porch is visible, adorned with potted greenery. A driveway leads to a closed garage, with a basketball hoop positioned nearby.

Apartment in Germantown

Private/Cozy Lower Level Apt-Great for Long Stays

Private entrance to One-bedroom apartment with Queen Bed, Full Bath, Lounge, Kitchenette/Dinette and Pool/Billiard Room. Perks include Wifi, Cable TV, Air-conditioning & Heating, Keurig Coffee Maker, Toaster, Microwave and Refrigerator, Hair Dryer, and Iron with Ironing board. Awesome safe neighborhood on a cul-de-sac, great landscape with a quiet & serene backyard facing wild life conservation land blending into Seneca Park trail. Perfect for a jog, or just read, and watch the deer and birds.

KitchenIndoor spacesHiking

4.98 out of 5 average rating, 244 reviews

A spacious sleeping area features a king-sized bed with a light-colored, textured duvet and decorative pillows. Two stylish lamps provide warm illumination beside the bed. A decorative bench sits at the foot of the bed, with neatly folded linens displayed on top. Natural light enters through a window with wooden blinds.

Guest suite in Derwood

Cozy, Private Garden Apt in Derwood-La Belle Vie

Spacious one bedroom basement apartment. Private entrance, full bathroom and kitchenette all newly done. Freshly landscaped slate patio with garden and pond. The sound of running water provides a relaxing environment. Secluded back yard backs up to beautiful woods. 5 min away from bike trails. Large, open living space with sectional couch, and attached eating area with a table that can double as a work station. Centrally located in Montgomery County-approx 40 minutes from DC/Baltimore/Frederick.

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 145 reviews

A modern kitchen features a large island with bar seating and granite countertops. Stainless steel appliances and a six-burner gas range are present. Soft natural light filters through a window, illuminating a cozy living area with a comfortable sofa and decorative accents.

Guest suite in Glenelg

Lovely guest house with gourmet kitchen & King bed

If you're looking for a quick getaway or a brewery hopping good time we offer that and everything in-between. Locally offerings include walking trails/ restaurants, and family farms. We are located between Washington D.C. and Baltimore. Only a short 45 minute drive to D.C., you can spend the day exploring the museums and sites that the Nations Capital has to offer. Baltimore is 25 minutes away. A great place to see the National Aquarium. You will love your relaxing stay here in this rural area

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 225 reviews

Home in Bethesda

Stylish Spacious Greentree Apartment

This 1,500 sq ft spacious luxury apartment is located in the lower level of a private custom home. NO SHARED HVAC. Sunny and light bedrooms with top-notch finishes and décor. Private entrance and walkway, covered porch, and free on-site parking for 2 cars. Prime Bethesda location: 1 mile to NIH and Naval Medical with public transportation just outside the front door. Bus 47 (free to ride) takes 10 minutes to Bethesda Metro station (Red-line) or in the opposite direction to Montgomery Mall.

Indoor spacesKitchenAmenities

4.87 out of 5 average rating, 144 reviews

A spacious outdoor area features a large in-ground pool surrounded by a patio. Lounge chairs in a bright blue color are arranged along the edge. A picnic area with tables and chairs is also visible, along with a children's play area nearby.

Home in Lovettsville

COZY3500sf Private-10acres Pool-PickleBall-Hot Tub

Immerse yourself in tranquility and laid-back luxury in our expansive home adorned with 6 cozy furnished bedrooms. Hemingway Retreat is nestled with 10 acres of spectacular farmland, with awe-inspiring vistas of horses grazing peacefully a picture-perfect escape from your routine life. With amenities such as fire pits, enjoyable hot tub, & tennis courts, indulge in a variety of recreational activities. Experience the fusion of comfort & exciting adventures at every corner of our property.

KitchenFamilyBackyard

Apartment in Gaithersburg

A bright sleeping area features a spacious bed with decorative pillows arranged neatly. A large area rug adds a pop of color, while natural light filters through windows adorned with light curtains. A potted plant hangs nearby, complementing the modern decor.

Bright Modern Boho Studio Apt | off I-270

Enjoy this private and sunny basement apartment and garden patio- a great home base after being out during the day. Located close to I-270, two hospitals, AstraZeneca, NIST, retail areas such as RIO, outlets, Bethesda, and in walking distance to a lake at Great Seneca Park State Park. The DC Metro train is 15 minutes away. The studio (1 queen bed) comes equipped to comfortably host a couple sightseeing or a traveling professional. Please read FULL description before booking.

FamilyKitchenValue

4.91 out of 5 average rating, 106 reviews

4.92 out of 5 average rating, 412 reviews

The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.

Cottage in Leesburg

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

FamilyIndoor spacesCondition

4.92 out of 5 average rating, 165 reviews

Home in New Market

Historic Peace and Plenty Farm: Pool House

Peace and Plenty Farm is a 40+ acre, stunning rural escape located in Frederick County, two miles from Historic New Market, 45 minutes from Gettysburg, and an hour from Baltimore or Washington D.C. Feel free to explore our farm’s trails and hidden gems, play yard games with the family, or swim in our lap pool (open from June through October). Our generous space is suitable for a couple's getaway, a weekend with friends, a family vacation, a working vacation, or a quiet retreat.

FamilyIndoor spacesView

4.98 out of 5 average rating, 110 reviews

A charming white farmhouse is set against a backdrop of rolling hills, with a vibrant row of sunflowers blooming in the foreground. The open pasture offers a serene landscape, enhanced by the warm light of the setting sun casting a gentle glow.

Farm stay in Mount Airy

Sunsets from a Haven on a Hill

Come rest & relax in the high hill country of Mount Airy, MD. Find an oasis of beautiful views, rolling hills, open skies, and pastureland. This three-story farmhouse sits on one of the highest points in Mount Airy, MD with views of both the sunrise and the sunset. With an open kitchen plan, large family room, and beds to sleep 9, it’s a perfect place to gather family together for the holidays. Unwind, unplug, and connect with your loved ones in this beautiful farm setting.

FamilyKitchenCheck-in

An outdoor patio area features a hot tub, a dining set, and a grill. A shaded seating area is furnished with cozy couches, while a colorful game board adds a playful element. Lush grass covers the ground, creating a welcoming space for relaxation and enjoyment.

4.99 out of 5 average rating, 289 reviews

Modern 3-Level Stay| Hot Tub | Game Room | Parking

Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

Indoor spacesFamilyWi-Fi

4.92 out of 5 average rating, 161 reviews

Home in Adamstown

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist as you immerse yourself in 2 thrilling themed escape rooms. Perfect for large family gatherings, bachelorette/bachelor/birthdays. Spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Weddings/Events/Pool additional cost. Follow us on Insta for more videos. Book your favorite Gamekeeper's Hut next door for larger parties.

KitchenFamilyAmenities

Superhost

Apartment in Gaithersburg

Private 2BR Suite | Free Parking | Walk to RIO

Your own private 2-bedroom basement suite. Separate entrance, two queen beds, full bath, kitchenette, and a real desk. Free assigned parking. Fast WiFi. Keypad entry after 3PM. Nobody else in the space. 5 minutes to NIST and AstraZeneca. 10 to Adventist Shady Grove and the Red Line. A 15-minute walk to RIO Washingtonian Center for waterfront dining, Target, and an AMC theater. Work trip, DC weekend, or family visit, this is a home base instead of a hotel room.

KitchenIndoor spacesShared spaces

4.85 out of 5 average rating, 110 reviews

Popular amenities for Montgomery Village family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A bright and inviting bedroom features a spacious bed adorned with decorative pillows. A light rug lies under a bench in front of the bed. Soft curtains frame the windows, and a mirrored dresser adds a touch of elegance to the room.

4.96 out of 5 average rating, 132 reviews

Lux Family Xcape with HotTub, Fireplace, Deck, BBQ

Indoor spacesKitchenLocation

4.97 out of 5 average rating, 115 reviews

A tranquil pool area is showcased at dusk, with soft purple lighting illuminating the water. Lounge chairs line the poolside, and trees surround the space, creating a calm and serene environment. The moon is visible in the clear sky, enhancing the peaceful ambiance.

Tent in Westminster

Rest and Recharge Retreat

Indoor spacesKitchenLocation

5.0 out of 5 average rating, 114 reviews

Cottage in Arlington

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Indoor spacesFamilyWi-Fi

4.91 out of 5 average rating, 135 reviews

Cabin in Walkersville

Walkersville Cabin

KitchenFamilyValue

4.89 out of 5 average rating, 103 reviews

Apartment in Takoma Park

Comfortable Space at a Great Location

KitchenIndoor spacesShared spaces

Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

Indoor spacesFamilyTV

4.94 out of 5 average rating, 218 reviews

4.98 out of 5 average rating, 207 reviews

A spacious living area features plush seating in elegant patterns, arranged around a round coffee table. Decorative lamps provide soft lighting, while rich red wallpaper and floral accents contribute to a warm atmosphere. A flat-screen TV is mounted on the wall, complemented by tasteful decor.

Home in Frederick

Romantic Getaway-Heated Spa - Seasonal Pool!

Indoor spacesKitchenLong stay

A covered patio is illuminated by string lights, featuring a gas fire pit surrounded by seating. A barrel sauna stands prominently, with a reflective door, offering a unique design. The gravel surface complements the outdoor space, creating an inviting atmosphere for relaxation.

4.96 out of 5 average rating, 104 reviews

Sauna, hot tub, great outdoor space!

KitchenIndoor spacesPets

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 133 reviews

A modern living area is highlighted by a comfortable sectional sofa adorned with colorful cushions. A round coffee table sits in front, with a decorative item placed on top. Large windows allow natural light to illuminate the space, framed by soft curtains and offering views of greenery outside.

Apartment in Sterling

The Potomac Perch-Peaceful Cozy Family Apt

KitchenFamilyBathroom

4.99 out of 5 average rating, 131 reviews

A well-lit bedroom features a vintage white metal bed frame with a soft gray blanket and pillows. A wooden dresser and a mirror are positioned beside a rocking chair, while two bedside lamps provide warm illumination. Light flows through the window, flanked by sheer curtains.

Home in Ashburn

Ashburn Manor: 1920’s Farmhouse

KitchenIndoor spacesHospitality

5.0 out of 5 average rating, 149 reviews

Farm stay in Leesburg

The Forge on Sunnyside Farm

FamilyIndoor spacesBreakfast

A charming brick home is set in a lush green landscape, featuring a well-manicured front yard with a spacious driveway. Trees provide shade, and a stone wall adds structure to the front garden. A garage is visible in the background, enhancing the property's character.

4.99 out of 5 average rating, 248 reviews

Entire Guest Suite/Apt in Silver Spring/FDA/NSA

FamilyIndoor spacesParking

4.97 out of 5 average rating, 146 reviews

A well-appointed living area features a spacious sectional sofa and an adjoining dining space. Large windows allow natural light to illuminate the room, creating a bright atmosphere. The kitchen is visible in the background, featuring high-end appliances and modern design elements.

Home in Sterling

The Villa on Lakeside

Indoor spacesKitchenWalkability

4.94 out of 5 average rating, 238 reviews

An inviting living space featuring a spacious L-shaped couch adorned with vibrant throw pillows. A glass dining table is positioned in the foreground, complemented by a bottle of rosé and two glasses. A modern kitchen with stainless steel appliances and bar seating can be seen in the background.

Guesthouse in Rockville

Modern Farmhouse Apartment. Close to Metro

KitchenIndoor spacesCleanliness

Superhost

The spacious living area features a comfortable gray sofa across from a mounted television and a foosball table. Multiple pieces of colorful artwork adorn the walls. Natural light filters through the front door and windows, illuminating the inviting space.

Home in Rockville

Spacious 5 Bedroom Entire Home Near Washington DC

Indoor spacesFamilyPets

4.81 out of 5 average rating, 377 reviews

4.94 out of 5 average rating, 141 reviews

The U.S. Capitol building is centered in the image, showcasing its iconic dome and neoclassical architecture. Vibrant red flowers bloom in the foreground, providing a colorful contrast against the blue sky and white façade of the building. Lush green trees flank the scene.

Home in Falls Church

Large DC, Tysons, McLean, Falls Church Mansion, VA

FamilyKitchenWi-Fi

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 181 reviews

The pool area features a crystal-clear pool bordered by stone pavers and landscaped greenery. A pool house with large glass doors is visible in the background, accompanied by a defined hot tub and neatly arranged lounge chairs. Surrounding trees and bushes enhance the outdoor setting.

Guesthouse in Monrovia

Poolside Paradise in Monrovia, Maryland.

FamilyIndoor spacesLocation

Townhouse in Fairfax Station

A living area is highlighted by a deep green accent wall and a flat-screen television mounted above a decorative rug. A comfortable sofa with throw pillows sits adjacent to a small dining table with a chair. A potted plant adds a touch of greenery to the space.

Cozy Private Entry 1BR1BA Suite Close to GMU & DC

Indoor spacesKitchenBackyard

4.9 out of 5 average rating, 115 reviews

Farm stay in Cockeysville

The Master's Suite · King Suite, Hunt Valley

FamilyIndoor spacesAir conditioning

4.95 out of 5 average rating, 147 reviews

Guest suite in Catonsville

A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.

Rollingside: Two-Room Guest Suite

Indoor spacesKitchenQuiet

4.94 out of 5 average rating, 584 reviews

Guest suite in Silver Spring

A charming bungalow is surrounded by vibrant greenery, featuring a welcoming front porch with decorative railings. The well-kept garden includes various plants and trees, while a wooden trellis adds an element of structure to the outdoor space.

Sophisticated Studio Apartment, Metro DC

FamilyKitchenCleanliness

4.96 out of 5 average rating, 311 reviews

4.95 out of 5 average rating, 104 reviews

Guest suite in Herndon

Capital Escape-Unique Spacious 2BR/1BA Apartment

FamilyKitchenParks

4.83 out of 5 average rating, 158 reviews

A cozy sleeping area is presented with a spacious bed dressed in soft, light-colored bedding. Two bedside lamps provide warm illumination, complementing the neutral tones of the walls. A small side table and a wooden accent table are positioned beside the bed.

Guest suite in Oakton

N. Virginia convenience to DC and Old town Vienna

KitchenFamilyView