Caroline County Holiday Homes
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Featured Holiday Homes in Caroline County

Charming 3-bedroom Ranch in delightful Dover with AC
Dover DE
During your stay at this holiday home, you'll be within walking distance of Carrolls Center Shopping Center. Laundry facilities are available. 2 bathrooms and a TV are available in the holiday home.
Waschmaschine
Wäschetrockner

Cozy cottage on the Miller farm.
Milford DE
Our customers tell us they can't get enough of this holiday home's great beach location. During your stay, you're just a quick walk from Abbott's Mill Nature Center. Enjoy features like laundry facilities. The holiday home offers a kitchen and a Smart TV.
Küche
Waschmaschine

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge MD
The price is CHF 270 per night
CHF 270
2 Feb - 3 Feb
includes taxes & fees
During your stay at this holiday home, you're just a quick walk from Long Wharf Park. You'll find features such as breakfast (surcharge) and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Greenwood DE
You'll find features such as laundry facilities at this holiday home. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Cambridge MD
During your stay at this holiday home, you'll be close to Spocott Windmill. Enjoy features like an outdoor pool, laundry facilities and an arcade/games room. The holiday home offers free WiFi and a private pool.
Pool
Küche

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
During your stay at this holiday home, you'll be close to Woods Island. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
St. Michaels MD
During your stay at this holiday home, you're just a quick walk from Higgins Yacht Yard and Marina. Enjoy features like laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.
Küche
Waschmaschine

Wind Song Getaway on the Beach
Frederica DE
During your stay at this holiday home, you'll be close to Logan School. You'll find features such as a water park and laundry facilities. Free WiFi and a kitchen are available in the holiday home.
Küche
Waschmaschine

Waterfront Estate w Private Pier, Game Room & Bar
Centreville MD
During your stay at this holiday home, you'll be close to Earle Landing. You'll find features such as free WiFi in public areas, plus laundry facilities and an arcade/games room. The holiday home includes amenities such as free WiFi and a kitchen.
Küche
Waschmaschine

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Frederica DE
During your stay at this holiday home, you'll be close to Logan School. You'll find features such as 1 hot tub and laundry facilities. The holiday home includes amenities such as a kitchen and a patio.
Whirlpool
Küche

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Chestertown MD
During your stay at this holiday home, you're just a quick walk from River Arts Chestertown. Features include laundry facilities. The holiday home includes amenities such as 3 bathrooms and a washing machine.
Waschmaschine
Wäschetrockner

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Easton MD
During your stay at this holiday home, you'll be close to Oxford Museum. An outdoor pool, 1 hot tub and laundry facilities are available. The holiday home offers free WiFi and a private pool.
Pool
Whirlpool

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford MD
During your stay at this holiday home, you'll be close to Ragged Island. You'll find features such as an outdoor pool, 1 hot tub and concierge services. The holiday home offers free WiFi and a private pool.
Pool
Whirlpool

Captain's Quarters
Frederica DE
Our customers tell us they can't get enough of this holiday home's great beach location. During your stay, you'll be close to Logan School. Features include a water park and laundry facilities. The holiday home includes amenities such as free WiFi and in-room jetted baths.
Küche
Waschmaschine

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Sherwood MD
During your stay at this holiday home, you'll be close to Back Creek Community Park. Features include 1 hot tub and laundry facilities. The holiday home includes amenities such as a private pool and a kitchen.
Pool
Whirlpool
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View all propertiesLowest 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.
Caroline County Holiday Homes essential information
Accommodation | 311 Holiday Homes |
|---|---|
Lowest Price | CHF 270 |
Highest Price | CHF 270 |
Popular accommodation | Charming 3-bedroom Ranch in delightful Dover with AC, Cozy cottage on the Miller farm. , 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, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Wind Song Getaway on the Beach, Waterfront Estate w Private Pier, Game Room & Bar, 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!!, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton., Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock, Captain's Quarters, 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access |
