Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

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Top guest favorite

A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.

Cottage in North East

4.97 out of 5 average rating, 599 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 the day of your arrival.

Top guest favorite

A spacious yard is bordered by wooden fencing and shaded by mature trees. Freshly mowed grass creates an inviting outdoor area. Nearby, a well-maintained cottage and additional structures are visible, providing a serene setting for relaxation and outdoor activities.

Cottage in Charlestown

4.97 out of 5 average rating, 107 reviews

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

Guest favorite

An outdoor seating area features comfortable gray cushions and a dark wooden coffee table, positioned on a deck overlooking a serene waterfront. The vibrant sunset casts warm hues across the sky, reflecting on the calm water, creating a tranquil atmosphere.

Cottage in Charlestown

4.95 out of 5 average rating, 206 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Guest favorite

A historic three-story house is framed by tall trees, showcasing a porch with white rocking chairs. The facade features a blend of stone and siding, accented by red shutters. Decorative lights and landscaping enhance the welcoming exterior. The lawn is grassy and well-maintained.

Apartment in North East

4.9 out of 5 average rating, 129 reviews

Heart of Downtown NE Apt!

Updates: we have updated the master bed to a king. We have also updated the living room sleeper sofa! We try to check in as often to keep the space comfy and fresh. Spacious 2 bed, 1 bath 2nd floor apartment located in the heart of downtown North East! Located directly on Main Street right in the heart of all restaurants and shopping. Located a short walk (and even shorter drive) to the marina. Park your car and don’t worry about a thing! Please note it can sleep 6 adults and 2 children.

Top guest favorite

A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.

Home in Perryville

4.99 out of 5 average rating, 130 reviews

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Guest favorite

A charming two-story red brick home features large windows with black shutters, allowing ample natural light to enter. Lush green landscaping surrounds the entrance, which includes a white front door flanked by elegant outdoor sconces. The overall impression reflects a well-maintained historic residence.

Home in North East

4.94 out of 5 average rating, 128 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.

Top guest favorite

A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.

Guesthouse in Elk Mills

4.98 out of 5 average rating, 141 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Guest favorite

The cottage exterior features a white vinyl facade, framed by black shutters on the windows. A welcoming front porch with steps leads to a glass door, complemented by flowering plants in front, with a well-maintained lawn and clear evening lighting enhancing the inviting ambiance.

Cottage in North East

4.94 out of 5 average rating, 382 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.

Top guest favorite

A bright and serene bedroom features a spacious bed with a light-colored quilt and decorative pillows. Two large windows offer natural light and views of lush greenery outside. A vintage dresser sits beside the bed, complemented by a nearby radiator.

Townhouse in Port Deposit

4.96 out of 5 average rating, 228 reviews

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

Top guest favorite

A retro-styled kitchen and living area showcase soft blue armchairs positioned on a patterned rug. Above the kitchen counter, colorful Pyrex dishware is neatly arranged on open shelves. Modern appliances, including a stainless steel stove, complement the bright cabinetry and accentuate the inviting atmosphere.

Apartment in Havre de Grace

5 out of 5 average rating, 170 reviews

Retro Downtown One Bedroom at JoRetro

Enjoy a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four retro 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

Top guest favorite

The interior of the cottage features rustic wooden beams and stone walls, creating a charming ambiance. A staircase leads to a lofted area. An inviting dining table sits at the center, surrounded by open living and workspace areas, equipped with various comfortable furnishings.

Cottage in Port Deposit

4.94 out of 5 average rating, 287 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.

Top guest favorite

A two-story house is presented, featuring a light grey exterior with dark blue shutters. A front door is highlighted by a small porch, while a garage is integrated on the right. A paved pathway leads toward the entrance, surrounded by a well-kept lawn.

Guesthouse in Havre de Grace

4.89 out of 5 average rating, 287 reviews

Studio apartment with off street parking

Private studio apartment just minutes away from the mouth of the Chesapeake Bay. Visiting our small town of Havre de Grace for a wedding or a local event, choose to relax in our sports themed comfortable home away from home. Havre de Grace has a lot of wonderful events, shops and restaurants to offer, and you will be just steps away from them.