Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 185 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Guest favorite

Tiny home in Cambridge

4.89 out of 5 average rating, 555 reviews

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!

Guest favorite

Rental unit in Frederica

4.98 out of 5 average rating, 121 reviews

Entire 1-Bedroom apt. - Private entrance in home

This centrally located, clean, 2nd floor apartment is the perfect place to rest. Features very large bedroom with a new king bed with a hybrid mattress, and spacious living room with a queen size pull out couch. Well equipped kitchen with toaster oven, electric skillet, countertop burner, microwave, and coffee makers (single chip and drip). Only 3 mi. to DE Turf, 15 mi. to Dover, and 30 mi. to the beaches! There are open stairs, so not appropriate for small children. Well-behaved pets welcome.

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 147 reviews

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)

Guest favorite

Home in Denton

4.95 out of 5 average rating, 114 reviews

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Easton, Dover, D.C. and Baltimore. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

Guest favorite

Rental unit in Greenwood

4.97 out of 5 average rating, 545 reviews

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)

Guest favorite

Casa particular in Chestertown

4.94 out of 5 average rating, 131 reviews

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!

Guest favorite

Rental unit in Magnolia

4.96 out of 5 average rating, 134 reviews

Perfect Rental for Dover Attractions & BayBeaches

15 minutes from Dover Nearby casinos, beaches, and the racetrack. Bowers and Slaughter beaches are about 10-15 mins from us, whereas, the major beaches like Rehoboth, Lewes and Dewey are 45mins to an hour from us. We are 5 mins from Highway 1 and located 15 mins from DE Sports Complex 10 mins from Highway 13 (Dupont Ave) Near the mall, casino, racetrack, shopping, and many restaurants. Killens Pond State Park is a 10 min drive. Harrington Casino the Del. State Fair is 15 mins from us.

Guest favorite

Rental unit in Frederica

4.96 out of 5 average rating, 285 reviews

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!

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 577 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 213 reviews

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.

Guest favorite

Rental unit in Church Creek

4.97 out of 5 average rating, 403 reviews

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.