We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Fairland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Fairland

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

0 of 0 items showing

1 of 3 pages

Cottage in Middletown

4.9 out of 5 average rating, 272 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

A spacious bedroom is presented with large windows offering views of a tranquil waterfront. A comfortable bed is paired with a white sofa, creating an inviting area. Natural light streams in, enhancing the warm wood accents throughout the room.

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.

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 154 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!

A charming stone cottage is set against a backdrop of lush trees and open sky. A gravel path leads to the entrance, with two chairs positioned on the grassy area, offering a serene view of the surrounding nature.

Cottage in Leesburg

4.92 out of 5 average rating, 402 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!

Top guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 148 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

A large tree provides shade over a grassy area, with a view of a calm waterfront. A wooden pier extends into the water, flanked by lush greenery. The scene is serene, evoking a sense of relaxation and natural beauty.

4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

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!

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

4.88 out of 5 average rating, 124 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!

A bright bedroom features a spacious bed dressed in neutral linens. Large windows provide natural light and views of an outdoor area with snow. A wooden dresser and desk complement the room's simple furnishings, while dark curtains frame the windows.

Home in Arlington

4.84 out of 5 average rating, 112 reviews

Next to Virginia Hospital Center

Welcome to your future home away from home! This stunning 5-bedroom single-family corner house is the epitome of comfort and convenience. -A step a way from VHC hospital. - Metro bus stop at the end of the block - 5 car parking lot - has access to house without stairs, and walk in shower for those experiencing difficulty with movement or stepping over tub. -sleeps 10 guests comfortably (3 queen beds, 4 twin beds) -1.4 miles from Ballston metro stop

Home in Annapolis

4.99 out of 5 average rating, 70 reviews

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

Top guest favorite

A quiet garden area features a stone pathway winding through vibrant greenery and blooming plants. The pathway is bordered by large shrubs and trees, creating a serene natural setting. A blue garden sign stands prominently among the foliage, adding a touch of color.

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Fairland vacation rentals

Free parking on premises

Air conditioning

Stay near Fairland's top sights

Target36 locals recommend

Adventist HealthCare White Oak Medical Center13 locals recommend

TGI Fridays12 locals recommend

Cuba De Ayer Restaurant11 locals recommend

Vocelli Pizza10 locals recommend

ALDI10 locals recommend

Other great vacation rentals in Fairland

A modern kitchen space is highlighted by a white countertop and sleek cabinetry. Bar stools are positioned at the kitchen island, and appliances are integrated into the design. Soft lighting accentuates the area, creating a bright and clean environment.

Apartment in Georgetown

4.88 out of 5 average rating, 116 reviews

Cozy Modern Apt. In G-Town

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

4.92 out of 5 average rating, 142 reviews

House in Edgewater Maryland

A custom-built residence is presented with a blend of stone and wood accents. Large windows illuminate the inviting front porch, surrounded by manicured landscaping and a lush green lawn. The two-story structure is set against a backdrop of trees, offering a sense of privacy.

Home in Annandale

4.94 out of 5 average rating, 18 reviews

Family Ready Dogs OK Ping Pong Backyard EV Charger

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

A row of charming urban townhouses features a blend of red brick and stone exteriors. A large tree stands in front, providing natural shade. The street is lined with parked vehicles, indicating a vibrant neighborhood. The sky is bright with scattered clouds.

Apartment in Canton

4.97 out of 5 average rating, 31 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

A rooftop terrace features six brightly colored blue chairs arranged around a small table, with expansive views of the water and cityscape beyond. The deck is made of light wood planks, and the clear sky enhances the vibrant scene.

Townhouse in Fells Point

4.96 out of 5 average rating, 136 reviews

Artsy, Historic Rowhouse with Striking Harbor Views

A balcony view is captured at night, featuring two chairs and a small table. A grill is positioned on one side, and string lights are softly glowing, creating a relaxed ambiance. The city's skyline and street lights are visible in the background.

Condo in Bethesda

4.89 out of 5 average rating, 188 reviews

Bright 2br w amazing loc and view

Quick stats about vacation rentals in Fairland

Total rentals
150 properties
Total number of reviews
2.3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Wifi availability
150 properties include access to wifi

Frequently Asked Questions

Do townhouse rentals in Fairland have free parking?
Absolutely! We offer over 30 townhouse rentals with free parking in Fairland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Fairland have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Fairland. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Fairland have wifi?
Absolutely! We offer over 30 townhouse rentals with wifi in Fairland. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Fairland?
Four-legged friends are welcome in Fairland. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in townhouse rentals in Fairland?
Experience the best of Fairland with our townhouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Fairland?
Fairland has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Fairland have a kitchen?
Absolutely! We offer over 70 house rentals with a kitchen in Fairland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Fairland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore