Cottages in Talbot County

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Featured Cottages in Talbot County

6 Mi to Dtwn: Family-friendly Home in Annapolis!
Stroll up to this charming two-story home with a welcoming front porch and garage, set amidst a beautifully manicured lawn.

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Stroll through the beautifully landscaped grounds to the central entrance, where a small porch and stairs lead to the main entrance.

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Front of property

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
2 Mi to Sandy Point State Park: Home w/ Deck!
Situated in a quiet suburban neighborhood, this single-story house features a well-manicured lawn and a wooden fence.

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Situated in a wooded area, this house features a front porch and a well-maintained lawn.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Bayfront Gem w/ Amazing Water Views + Pond!
Enjoy a serene ocean view from the covered deck, overlooking the water and adjacent grassy area.

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Pet-friendly Annapolis Home: Walk to Beach!
Enjoy a retreat with a covered porch and a spacious front section featuring large windows.

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Tranquil Port Republic Home w/ Water Views!
Relax on the deck with a clear view of the water, surrounded by a tranquil atmosphere.

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
Annapolis Home Near Beach & Quiet Waters Park!
Enjoy al fresco dining on the deck, surrounded by lush greenery and a clear sky.

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Charming single-story home with a front porch and garden area, surrounded by a fence and trees.

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
House (4 Bedrooms) | Interior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Interior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Beautiful Colonial Home on the Choptank River
Relax in a serene outdoor space with a clear view of the water and dock, surrounded by lush greenery and comfortable seating.

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Grasonville Home w/ Private Pool on the Water
Relax on the patio with a view of the serene lake, surrounded by lush greenery and a natural focal point.

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Updated North Beach Cottage: Pet Friendly!
Cozy home with a gabled roof and a welcoming front porch.

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Walk to Beach: Charming Maryland Home w/ Yard!
Stunning single-story home with a charming front porch and beautifully manicured lawn.

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!
Riverside House w/ Kayaks, Piano & Fireplace
Stylish two-story home with a garage, porch, and lawn.

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Situated in a lush environment, this house features a gabled roof and a covered porch.

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
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 Talbot County Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Beautiful place, very clean room, but the best thing by far was the staff. Everyone we met was friendly and helpful. Thank you so much for a greay stay!!"
Anonymous traveller 1-night trip
Posted 15 hours ago
Graduate by Hilton Annapolis