Vacation rentals in Darlington

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Top-rated vacation rentals in Darlington

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Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 111 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Sep 20 – 27

G$21,316 GYD per night

Guest favorite

Townhouse in Rising Sun

4.8 out of 5 average rating, 131 reviews

Small Town Vibes

Relax during your stay in a fully remodeled town home in the center of Small Town Rising Sun MD! There is so much to offer with the location and renovations of this town home… Local coffee shops, Grocery Store and restaurants in walking distance to quaint historical downtown Main Street. Also many actives are in the area like Ripken Stadium, an art studio and so much more! WiFi and basic necessity’s will always be included during your stay. We welcome you to come stay and relax while visiting!

Sep 22 – 29

G$24,763 GYD per night

Guest favorite

Home in Rising Sun

4.95 out of 5 average rating, 239 reviews

Home Away from Home in Rising Sun, MD

PLEASE READ: Children under 12 years of age are not suitable for this home. Check in:3-8pm can be flexible to fit your schedule.Check out: 11am This home has a living room, kitchen and dining area, two bedrooms and a full bath. No pets! THE THIRD BEDROOM is a master suite that can be added for an ADDITIONAL CHARGE. It includes a living area, queen bed, bathroom and kitchenette. Ask for more details. This home is very comfy and has a history room from family collectibles dating back to 1854.

Nov 12 – 19

G$28,907 GYD per night

Guest favorite

Guesthouse in White Marsh

4.97 out of 5 average rating, 140 reviews

Bird River Bottega - A Waterfront Oasis!

Private entrance studio located on a waterfront property. The Bottega is perfect for couples, solo travelers, and business professionals; best suited for two travelers. Enjoy your morning coffee by the water and watch the Ospreys, herons, ducks, hawks, and bald eagles galore. Whether you are fishing, lounging, or kayaking the Bird River (home to the Chesapeake Bay), you are bound for relaxation. Surrounded by a plethora of eateries, shopping, and entertainment all within a 25 minute drive.

Apr 20 – 27

G$18,781 GYD per night

Guest favorite

Apartment in Havre de Grace

5.0 out of 5 average rating, 101 reviews

Retro Downtown One Bedroom at JoRetro

Indulge in a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four meticulously decorated units, each inspired by an iconic Pyrex design. Relax on the queen-size bed, with luxury linens, and enjoy retro and vintage items, including Butterprint Pyrex pieces. Explore a variety of restaurants and unique shops, all within walking distance. Don't miss the opportunity to visit the historic Lighthouse and museums.

Oct 17 – 24

G$28,612 GYD per night

Guest favorite

Cottage in Aberdeen

4.95 out of 5 average rating, 148 reviews

Tranquil Carriage House*MCM *Country *Wildlife

Pet, and Chemical Free. The Aberdeen Carriage House is in a country setting with a country road. We are not far from city limits and have most of your needs right here. In five minutes, you have a grocery store, dollar store, Target, Walgreens, Planet Fitness, and restaurants. Historic Havre de Grace, Ripken Stadium, Vineyards, Boating, and Golfing, only ten minutes. Baltimore and Stadiums are only 35 minutes down I95. The house is spotless and fully loaded with all the comforts of home.

Jan 23 – 30

G$29,366 GYD per night

Guest favorite

Guesthouse in Quarryville

4.99 out of 5 average rating, 236 reviews

The Olde Wash House on Camargo

Come and relax in our newly remodeled, cozy, cottage style home with it's own private entrance, surrounded by working Amish farms, just outside of town. A short 15 minute drive to Historic Strasburg, Sight and Sound Theater, Antique Shopping, Tangor Outlets and more! Hiking Trails close by include Enola Grade Trail, Pinnacle Point, Muddy Run Park, and Sickman's Mill. If golfing is your desire, Tanglewood Golf Club is just 10 minutes away. We hope you enjoy your stay!

Jan 1 – 8

G$20,265 GYD per night

Guest favorite

Cottage in North East

4.97 out of 5 average rating, 439 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

Feb 3 – 10

G$23,057 GYD per night

Guest favorite

Cottage in North East

4.94 out of 5 average rating, 280 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Mar 16 – 23

G$20,443 GYD per night

Guest favorite

Guest suite in Darlington

4.97 out of 5 average rating, 262 reviews

Syd Acres

Unplugged retreat. Great for birders, piano players, gardening fans, antiquers. Twenty minutes from historic Havre de Grace. Nearby gardens include: Longwood Gardens; Chanticleer Garden; Winterthur Museum, Garden, and Library; and LaDew Topiary Gardens. Small kitchen with microwave, sink, fridge, and coffee maker. Private entrance. Smoke detectors, hair dryer. No WiFi. No stove.

Oct 7 – 12

G$43,920 GYD per night

Guest favorite

Apartment in Little Britain Township

4.96 out of 5 average rating, 236 reviews

Brick Hill farm guesthouse

Come stay on the farm where we aim to create an atmosphere of relaxation. It’s an opportunity to get away from the hustle and bustle of life. Start your day with a fresh cup of coffee or tea and enjoy the scenery from the rocking chairs on the porch. End the day gathering around the campfire if you wish. Whether you like the outdoors or not we hope you van rest & relax!

Jul 12 – 19

G$30,160 GYD per night

Guest favorite

Cottage in Port Deposit

4.91 out of 5 average rating, 172 reviews

The River Cottage

Take it easy in this unique cottage built in the 1800s nestled upon the Granite Cliffs of Port Deposit Maryland. While enjoying your tranquil get away you’re minutes from local shops, local dining, local wineries, local breweries and a local marina. There is plenty of sightseeing and wildlife. If you enjoy fishing and kayaking it’s just a short distance away.

Mar 29 – Apr 5

G$46,394 GYD per night