Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

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Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 49 reviews

Long Beach Cottage, (romantic couple’s getaway)

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

Dec 9 – 16

ﺩ.ﺇ1,474 per night

Guest favorite

Hotel room in Charlestown

4.91 out of 5 average rating, 32 reviews

The Avalon at the Cooper House

Gorgeous 1 bed/1 bath suite offering incredible waterfront views of the North East River. King size bed, a convertible single bed, seating and tv area, outdoor seating with unmatched water front views and private entrance. Walk to marinas, fishing, restaurants, parks, tennis, and kayak launch, excellent porch sitting, and picture perfect sunrises. The Avalon is one of three suites available at The Cooper House and can be combined to accommodate larger groups, or kept separated, if desired.

Sep 28 – Oct 5

ﺩ.ﺇ468 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 7 – 14

ﺩ.ﺇ509 per night

Guest favorite

Apartment in Havre de Grace

5.0 out of 5 average rating, 139 reviews

Mid Century 2 Bedroom at JoRetro with a King Bed

Enjoy a newly renovated mid-century modern apartment in the heart of downtown Havre de Grace, located above our shop, JoRetro Vintage Market. We currently have 3 units to choose from. We have decorated this suite using the 1945 Pyrex Primary bowls for design inspiration. Find luxury amenities and authentic Vintage items throughout the apartment, including Pyrex! Walk to restaurants and unique shops. Visit the lighthouse and museums. Enjoy a show at the Opera House or the State Theater.

Mar 20 – 27

ﺩ.ﺇ590 per night

Guest favorite

Cottage in North East

4.97 out of 5 average rating, 436 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.

Mar 18 – 25

ﺩ.ﺇ406 per night

Guest favorite

Home in Charlestown

4.96 out of 5 average rating, 25 reviews

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!

Dec 3 – 10

ﺩ.ﺇ639 per night

Guest favorite

Cottage in North East

4.94 out of 5 average rating, 279 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.

Nov 24 – Dec 1

ﺩ.ﺇ360 per night

Guest favorite

Cottage in Port Deposit

4.91 out of 5 average rating, 170 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.

Oct 10 – 17

ﺩ.ﺇ817 per night

Guest favorite

Apartment in Rising Sun

4.97 out of 5 average rating, 197 reviews

Cross Keys Tavern

Built in 1744, this lovely home is the perfect country getaway. Cozy apartment in a historic property located in the little town of Calvert. Huge master bedroom with plenty of relax room. Private entrance with plenty of parking. Six miles from Fair Hill Natural Resources Area and a golf course practically in the back yard.

Feb 25 – Mar 4

ﺩ.ﺇ524 per night

Guest favorite

Guest suite in North East

4.92 out of 5 average rating, 12 reviews

1 Bedroom Apartment @Cool Springs

Newly constructed ground floor (basement) 1 bedroom, 1 bathroom walk-out apartment, located in Charlestown, MD; a stone's throw away from the Charlestown Marina! The property is part of a newly developed residential neighborhood that is a short distance to local dining, shopping, and gorgeous views of the North East River.

Apr 30 – May 7

ﺩ.ﺇ330 per night

Guest favorite

Apartment in Chesapeake City

4.93 out of 5 average rating, 141 reviews

Bohemia Vista CC Horse Farm Apartment

Comfortable and private, 10 minutes from Chesapeake City This private apartment comes with a basic kitchen, private bedroom with king sized bed, common area twin bed, sitting area, bath with a jacuzzi tub, and expansive views of farmland and horses. Private entrance and use of private laundry room included.

Dec 19 – 26

ﺩ.ﺇ480 per night

Guest favorite

Guest suite in North East

4.95 out of 5 average rating, 116 reviews

The Cozy Studio of North East MD

Newly remodeled second floor unit in the town of North East and walking distance to restaurants, shops. This unit sleeps 4 and has an attached full bath and an eat-in kitchenette. BRING YOUR BOAT! This unit is walking distance to the water and has ample street parking for your boat.

Jun 14 – 21

ﺩ.ﺇ378 per night