Vacation rentals in Charlestown

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Top-rated vacation rentals in Charlestown

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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.

Jan 16 – 23

G$21,316 GYD per night

Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 51 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

Sep 17 – 24

G$98,477 GYD per night

Guest favorite

Hotel room in Charlestown

4.88 out of 5 average rating, 33 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.

Nov 9 – 16

G$26,527 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.

Oct 18 – 25

G$28,907 GYD per night

Guest favorite

Apartment in Havre de Grace

5.0 out of 5 average rating, 100 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.

Mar 21 – 28

G$28,612 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.

Mar 19 – 26

G$23,057 GYD 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!

Oct 2 – 9

G$37,121 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.

Dec 29 – Jan 5

G$20,443 GYD per night

Guest favorite

Apartment in Rising Sun

4.97 out of 5 average rating, 198 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.

Jan 10 – 17

G$29,740 GYD 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.

May 7 – 14

G$18,722 GYD per night

Guest favorite

Apartment in Chesapeake City

4.93 out of 5 average rating, 142 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 26 – Jan 2

G$27,244 GYD per night

Guest favorite

Guest suite in North East

4.95 out of 5 average rating, 117 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.

Jul 8 – 15

G$21,481 GYD per night