Talbot County Holiday Homes
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Featured Holiday Homes in Talbot County
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Annapolis MD
During your stay at this holiday home, you're just a quick walk from U.S. Naval Academy. Features include laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.
Küche
Waschmaschine
Large 2 bedroom house with private parking in a nice neighborhood
Arnold MD
The price is CHF 251 per night
CHF 251
4 Jan - 5 Jan 2026
includes taxes & fees
During your stay at this holiday home, you'll be close to Bay Hills Golf Club. Laundry facilities are available. The holiday home offers free WiFi and a kitchen.
Küche
Waschmaschine
The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach MD
During your stay at this holiday home, you'll be within walking distance of Bayside History Museum. Enjoy your stay with amenities like a kitchen and a patio in the holiday home.
Küche
Klimaanlage
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Annapolis MD
The price is CHF 1'012 per night
CHF 1'012
26 Jan - 27 Jan 2026
includes taxes & fees
During your stay at this holiday home, you're just a quick walk from U.S. Naval Academy. Enjoy features like breakfast (surcharge), concierge services and laundry facilities. The holiday home includes amenities such as free WiFi and in-room jetted baths.
Küche
Waschmaschine
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge MD
The price is CHF 276 per night
CHF 276
5 Jan - 6 Jan 2026
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
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Annapolis MD
Our customers tell us that they can't get enough of the pool at this holiday home. During your stay, you're just a quick walk from Annapolis Harbor. Free WiFi in public areas, an outdoor pool and breakfast (surcharge) are available. Enjoy your stay with amenities like free WiFi and a private pool in the holiday home.
Pool
Küche
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Annapolis MD
Our customers tell us they enjoy this holiday home's walkable location. During your stay, you're just a quick walk from U.S. Naval Academy. Features include laundry facilities. The holiday home offers free WiFi and a kitchen.
Küche
Waschmaschine
Location is perfect and a big bonus we have our own parking at the home!
Annapolis MD
During your stay at this holiday home, you're just a quick walk from U.S. Naval Academy. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and in-room jetted baths 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
200 steps to the beach!
Rock Hall MD
During your stay at this holiday home, you're just a quick walk from Chesapeake Bay. Laundry facilities are available. Enjoy your stay with amenities like a kitchen and 1.5 bathrooms in the holiday home.
Küche
Waschmaschine
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick MD
The price is CHF 325 per night
CHF 325
14 Jan - 15 Jan 2026
includes taxes & fees
During your stay at this holiday home, you're just a quick walk from Chesapeake Bay. You'll find features such as a water park and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Shewell's A-Frame on Mill Creek
Lusby MD
During your stay at this holiday home, you'll be within walking distance of Drum Point Lake. Features include laundry facilities. The holiday home offers a kitchen and 2.5 bathrooms.
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
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.
Talbot County Holiday Homes essential information
Accommodation | 787 Holiday Homes |
|---|---|
Lowest Price | CHF 251 |
Highest Price | CHF 1'012 |
Popular accommodation | Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Large 2 bedroom house with private parking in a nice neighborhood, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming garden row home, easy 4 block walk to the heart of Annapolis., Location is perfect and a big bonus we have our own parking at the home!, 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, 200 steps to the beach!, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Shewell's A-Frame on Mill Creek, Waterfront Estate w Private Pier, Game Room & Bar |