Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

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Superhost

Apartment in Chestertown

Secluded Cottage in Middle of Chestertown

Escape to a secluded, romantic studio getaway 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 every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, plus Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

$112 per night

Superhost

Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

$85 per night

Superhost

Apartment in Frederica

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

$60 per night

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Superhost

Tiny home in Cambridge

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

$73 per night

Superhost

Home in Cambridge

"Happy Campers" Waterfront Apartment!

Come and experience a relaxing getaway at our fully furnished, detached waterfront apartment! Happy Campers is located on the Choptank River, surrounded by acres of pristine land! You will enjoy quiet afternoons, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery! A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park!

$150 per night

Superhost

Guest suite in Chestertown

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

$109 per night

Superhost

Cottage in Saint Michaels

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

$204 per night

Superhost

Apartment in Church Creek

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

$115 per night

Superhost

Home in Cambridge

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

$128 per night

Superhost

Cottage in Saint Michaels

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

$193 per night

Superhost

Guest suite in Chestertown

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits 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.

$119 per night

Superhost

Guesthouse in Grasonville

Eastern Shore Charm on Winchester Creek

My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

$140 per night

Superhost

Cabin in Goldsboro

Wigwam Lodge~Hot Tub~MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

$181 per night

Superhost

Guesthouse in Centreville

Centreville Cottage

This eastern shore cottage is ideally located: a mile from downtown Centreville, 15 minutes to Kent Island, 20 minutes to Chestertown and Easton, and 30 minutes to Annapolis. The 600 square foot Cottage is completely detached from the main house and has a private, fenced-in yard (perfect for pets). Enjoy shore living at its best!

$100 per night

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Vacation rentals in Caroline County

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