Vacation Homes in Caroline County

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Top Cities in Caroline County

Our top choices for Caroline County holiday homes

Charming 3-bedroom Ranch in delightful Dover with AC

Charming 3-bedroom Ranch in delightful Dover with AC
Dover
10.0 out of 10, Exceptional, (1 review)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC

Cozy cottage on the Miller farm.

Cozy cottage on the Miller farm.
Milford
10.0 out of 10, Exceptional, (242 reviews)
"Wonderfully quiet location with amazing amenities and beautiful scenery."
United States
Jason A.
Cozy cottage on the Miller farm.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is HK$1,172
HK$2,817 total
includes taxes & fees
2 Mar - 3 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Greenwood
9.8 out of 10, Exceptional, (37 reviews)
"Great home and location for what we needed. Would stay here again.. "
United States
Matt F.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Cambridge
9.8 out of 10, Exceptional, (8 reviews)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.4 out of 10, Exceptional, (25 reviews)
"House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions we had. Everyone enjoyed their stay with many memories made."
United States
robert p.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels
9.8 out of 10, Exceptional, (48 reviews)
"Conveniently located!"
United States
Jennifer E.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Wind Song Getaway on the Beach

Wind Song Getaway on the Beach
Frederica
9.8 out of 10, Exceptional, (34 reviews)
"Location was nice, beautiful sunrises. Plenty of room, beds were super comfy and communication with owner was wondering!"
United States
Lisa K.
Wind Song Getaway on the Beach

Waterfront Estate w Private Pier, Game Room & Bar

Waterfront Estate w Private Pier, Game Room & Bar
Centreville
9.6 out of 10, Exceptional, (38 reviews)
"Great location and plenty of fun"
United States
Carl S.
Waterfront Estate w Private Pier, Game Room & Bar

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Frederica
9.4 out of 10, Exceptional, (3 reviews)
"Adorable cottage. Excellent location. We will definitely rent again. "
United States
Ed M.
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Chestertown
10.0 out of 10, Exceptional, (4 reviews)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Easton
10.0 out of 10, Exceptional, (11 reviews)
"Great property for a family summer vacation and to just relax by the pool, kayak, fish off the dock, and head to town for ice cream or crabs."
United States
Anonymous traveller
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford
9.8 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."
United States
Linda S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Cambridge
10.0 out of 10, Exceptional, (82 reviews)
"There were so many activities and so many beds/baths. Perfect for a large group."
United States
Ellen S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Captain's Quarters

Captain's Quarters
Frederica
9.8 out of 10, Exceptional, (109 reviews)
"The house was perfect for our family weekend together, very clean and comfortable."
United States
Christine D.
The price is HK$2,188
HK$4,139 total
includes taxes & fees
12 Mar - 13 Mar
Captain's Quarters

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Sherwood
10.0 out of 10, Exceptional, (22 reviews)
"This place is spacious, comfortable, and so clean. Well-maintained outdoor grounds, very nice and helpful caretaker, amazing to have access to boats/life jackets, golf cart, and fire pit!"
United States
Talia R.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge
9.8 out of 10, Exceptional, (133 reviews)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"
East New Market
10.0 out of 10, Exceptional, (2 reviews)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
United States
kathleen l.
Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Frederica
10.0 out of 10, Exceptional, (11 reviews)
"Very Interesting place to stayGood time had by all"
United States
Gregory H.
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Grasonville
10.0 out of 10, Exceptional, (27 reviews)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Caroline County Hotel Reviews

Find out more about Caroline County

Caroline County Vacation Homes information

Number of reviews
642
Accommodation
311 Vacation Homes
Lowest Price
HK$2,817
Highest Price
HK$4,139

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