Holiday rentals in Brookeville

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Brookeville

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

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Guest favourite

Home in Timonium

4.92 out of 5 average rating, 184 reviews

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

Guest favourite

Cottage in Middletown

4.9 out of 5 average rating, 269 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Guest favourite

Home in Lovettsville

4.83 out of 5 average rating, 106 reviews

Cozy 3500sf Private 10ac. pickleball-hot tub-pool

5/6 (6th bedroom has queen sofa bed) Bedrooms furnished w/linens and all your needs 10 private acres in Farm land views of horses Remodeled fully equipped Kitchen w/new appliances 5 full baths w/spa like showers 7 person hot tub 35,000 gallon in ground private pool opens May 25 Private Tennis Court (basic)/Basketball Court 2 Fire pits Picnic area with grills and patio furniture Kiddos play area w/swing sets and slides Large great room/family room 10 acres with 4 acres a forest Dining for 8+

Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 153 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favourite

Cottage in Leesburg

4.91 out of 5 average rating, 397 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Guest favourite

Flat in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Guest favourite

Home in Deale

4.98 out of 5 average rating, 104 reviews

No Pet fee! Waterfront Oasis 40 mins to DC !

3 Bedroom, 2 Bath Waterfront Paradise. This rustic rambler on Broadwater Creek in Churchton, MD, is a family vacation dream. A compound spanning 8 acres with over 700 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream. Located near the small quaint waterman town of Deale, MD, you may never want to leave this relaxing area with direct access to the Chesapeake Bay. Brand new 140ft pier with views straight out to the bay, crabbing, and fishing!

Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 122 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Guest favourite

Flat in Deale

4.91 out of 5 average rating, 620 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Guest favourite

Guest house in Frederick

4.98 out of 5 average rating, 177 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.

Top guest favourite

Guest house in Owings Mills

4.97 out of 5 average rating, 114 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.