Vacation rentals in Brookeville

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Top-rated vacation rentals in Brookeville

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

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.

FamilyLocationBreakfast

4.98 out of 5 average rating, 244 reviews

Guest favorite

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

LocationValueLaundry

4.98 out of 5 average rating, 145 reviews

Guest favorite

The main living area features exposed wooden beams above and a cozy sofa adorned with decorative pillows. A small dining table with chairs is positioned near a window, and a charming side table displays a decorative item. Natural light fills the space, enhancing its inviting atmosphere.

Guesthouse in Glenwood

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.

LocationValueAmenities

4.95 out of 5 average rating, 212 reviews

Guest favorite

A spacious kitchen area is highlighted by dark wood cabinetry and a black countertop. Pendant lights hang above the counter, and light wood flooring leads towards an open living space. Decorative wall art featuring floral motifs is displayed on the yellow walls.

Guest suite in Highland

"The Whole First Floor is Yours" near Columbia, MD

Welcome to the American Dream! Our home is set in a picturesque suburban neighborhood of the nation's capital. On our first floor (2000 square feet), we have two separate rooms with three beds, 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, or a group of friends, welcome! My home is also close to Merriweather concert!

ValueFamilyBackyard

4.79 out of 5 average rating, 152 reviews

Top guest favorite

An inviting family room features a pool table at its center, surrounded by comfortable seating and dining areas. Natural light illuminates the space through large doors leading to the deck. Ceiling fans and a warm color palette contribute to the open, relaxed atmosphere.

Home in Columbia

Rancher by Wash/Balt/Annap w/pool table, Kit, Deck

My Columbia House sits between Baltimore, Washington DC, and Annapolis, plus Historic Ellicott City, (county seat), is 8 miles close. The kid friendly neighborhood is central to Columbia village centers offering shops, restaurants, entertainment, lakes, hiking trails + more. Guests will enjoy FiOS Quantum data-multiple Laptop friendly work areas, 2 TVs and data jacks thru-out the home. See owners' favorites' list for local treats like Savage Mill, Ellicott City, or Merriweather Post Pavilion

LocationFamilyBathroom

4.94 out of 5 average rating, 120 reviews

Top guest favorite

A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.

Guesthouse in Highland

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 (weather permitting) and adjacent walking trails.

ValueFamilyCleanliness

4.98 out of 5 average rating, 313 reviews

Guest favorite

The modern lakeside home is framed by lush trees, featuring multiple levels and large windows that allow natural light to fill the interiors. A gravel area with seating and a fire pit sits in the grassy yard, providing a cozy outdoor space for gatherings.

Home in Gaithersburg

DMV 4BR Luxury LakeHouse - GameRoom Firepit

Welcome home to a modern, luxurious, unique, extra RARE, and serene 4BR lakeside retreat with a lake in the backyard. Your relaxing haven in nature's embrace, yet near city buzz. Minutes to DC, NoVA, Baltimore, dining, and shopping. Enjoy the entire house, including 4 bedrooms, 4 full baths, 3 living/family rooms, a Game Room with an Arcade and pool & foosball tables, gym equipment, and, to top it off, a rooftop deck with lake views. Amenities abound. Have a great time with family.

LocationFamilyNearby

4.91 out of 5 average rating, 79 reviews

Top guest favorite

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.

Home in Silver Spring

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!

LocationFamilyTV

4.99 out of 5 average rating, 289 reviews

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.

LocationFamilyBiking

4.85 out of 5 average rating, 111 reviews

Superhost

Townhouse in Gaithersburg

Maryland DC 4BR/3.5b Townhome + Gameroom & Grill

Escape to our serene 3-story lakeside townhouse in Gaithersburg, MD, ideal for families and groups of up to 11. This spacious 4BR/3BA home features a game room, cozy fireplace, fully equipped kitchen, and two private decks with peaceful nature views. Enjoy a lower patio lounge with direct access to walking trails and the lake. Quiet, family-friendly location near DC, Baltimore, and local attractions—your perfect home away from home.

FamilyLocationWifi

4.68 out of 5 average rating, 121 reviews

Top guest favorite

Home in Silver Spring

5BD Family Retreat | Backyard·Arcade·Near DC

FamilyLocationWalkability

4.97 out of 5 average rating, 125 reviews

Guest favorite

A historic home constructed from stone is situated amidst lush greenery. The house features a wraparound porch with white railings and several tall windows. A smaller stone building is visible in the foreground, surrounded by expansive lawns and trees.

Farm stay in Brookeville

Farmstay in a Historic Home

Enjoy relaxing in a peaceful historic home on a working 500 acre farm steeped in history. Hosted by farmers but central to Baltimore, Washington and Frederick. Across from Patuxent State Park. Enjoy hiking on the farm or in the park, fishing in the pond, fresh veggies from the garden, farm animals that amuse or read a book with your feet in the creek. Individual fun but well suited to small events of any ilk.

LocationFamilyHospitality

4.89 out of 5 average rating, 38 reviews