Orlofseignir í Church Hill

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Church Hill: Vel metnar orlofseignir

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Gestaíbúð í Chestertown

4,99 af 5 í meðaleinkunn, 98 umsagnir

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

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Heimili í Chestertown

4,97 af 5 í meðaleinkunn, 29 umsagnir

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

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Heimili í Chestertown

5 af 5 í meðaleinkunn, 18 umsagnir

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. And yes, we also have a 420-friendly space. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

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Gestaíbúð í Chestertown

4,99 af 5 í meðaleinkunn, 228 umsagnir

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

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Gestaíbúð í Chestertown

4,98 af 5 í meðaleinkunn, 165 umsagnir

Chestertown - Eastern Shore Getaway

This century-old three-story home is in the beautiful historic district of Chestertown on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. (NOTE - Airbnb adjusts our rate according to the current demand for rooms)

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Heimili í Chestertown

4,97 af 5 í meðaleinkunn, 134 umsagnir

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

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Bústaður í Charlestown

4,95 af 5 í meðaleinkunn, 184 umsagnir

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

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Casa particular í Chestertown

4,92 af 5 í meðaleinkunn, 153 umsagnir

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

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Bændagisting í Centreville

5 af 5 í meðaleinkunn, 40 umsagnir

No Fees~Historic Lansdowne Manor

☞ Lansdowne is significant as one of the finest and best preserved examples of Federal period domestic architecture in the region, according to the Library of Congress. ☞ 1 King bed ☞ 3 Queen beds ☞ 2 Full bed ☞ Backyard and fire pit ☞ 198 Mbps wifi ☞ 2 Smart TVs (largest is 55 inches) ✭ ✭ ✭ ✭ ✭ “Great, historic home. Charming and well kept.” ☞ Pet friendly ☞ Gas grill ☞ Fully equipped+stocked kitchen ☞ Self check-in ☞ Onsite washer/dryer ☞ Air conditioning 》60 mins to airport

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Íbúð í Chestertown

4,96 af 5 í meðaleinkunn, 240 umsagnir

Private cozy cottage - center of Chestertown .

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

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Íbúð í Chestertown

5 af 5 í meðaleinkunn, 114 umsagnir

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

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Heimili í Greensboro

4,97 af 5 í meðaleinkunn, 101 umsagnir

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.