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.

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 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!

Nov 29 – Dec 6

$73 per night
Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 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.

Aug 16 – 23

$108 per night
Superhost

Apartment in Grasonville

4.89 out of 5 average rating, 173 reviews

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to some restaurants.

Feb 7 – 14

$146 per night

Popular amenities for Caroline County vacation rentals

Other great vacation rentals in Caroline County

Guest favorite

Houseboat in Grasonville

4.99 out of 5 average rating, 113 reviews

Cass-Away A Luxury Houseboat

Feb 2 – 9

$150 per night
Guest favorite

Home in Kent Narrows

5.0 out of 5 average rating, 275 reviews

Chester Riverfront At Kent Narrows

Nov 6 – 13

$331 per night
Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Feb 5 – 12

$113 per night
Guest favorite

Home in Preston

4.96 out of 5 average rating, 25 reviews

Bay Country Cottage

Oct 5 – 12

$151 per night
Superhost

Home in Denton

4.89 out of 5 average rating, 76 reviews

Historic 19th Century Eastern Shore Farmhouse

Aug 4 – 11

$160 per night
Guest favorite

Guesthouse in Wye Mills

4.93 out of 5 average rating, 15 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

Nov 18 – 25

$74 per night
Guest favorite

Farm stay in Denton

5.0 out of 5 average rating, 10 reviews

Lyford Landing Farmhouse

Feb 13 – 20

$232 per night
Guest favorite

Home in Preston

4.98 out of 5 average rating, 57 reviews

River House on the Choptank

Jan 10 – 17

$205 per night
Guest favorite

Bungalow in Queen Anne

4.94 out of 5 average rating, 48 reviews

Private bungalow with fire pit near Easton, Denton

Feb 7 – 14

$199 per night
Guest favorite

Home in Denton

4.94 out of 5 average rating, 70 reviews

Mallard Landing Townhouse

Jul 28 – Aug 4

$349 per night
Guest favorite

Apartment in Kent County

4.92 out of 5 average rating, 73 reviews

Furnished country apartment!

Oct 24 – 31

$86 per night
Guest favorite

Apartment in Frederica

4.99 out of 5 average rating, 88 reviews

Entire 1-Bedroom apt. - Private entrance in home

Nov 3 – 10

$95 per night

Destinations to explore