Cottages in Talbot County

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Top Cities in Talbot County

Our top choices for Talbot County cottages

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (198 reviews)
"Great property! The house has everything you'd need and the location couldnt be better. "
United States
Joe C.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (15 reviews)
"Amazing property well presented with fantastic views in all directions"
United Kingdom
David G.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (265 reviews)
"The hosts were very welcoming, helpful, good communication throughout the reservation process and stay."
United States
Ann R.
Family and Pet-Friendly, Waterfront with Pier

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (62 reviews)
"great stay ! all needs where met . "
United States
randall j.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (126 reviews)
"Ideal location to shops and attractions. Host very easy to reach. "
United States
Don N.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Incredible property and stay."
United States
Hunter B.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Peaceful getaway convenient to local amenities including beach, boating & food

Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall
9.8 out of 10, Exceptional, (119 reviews)
"Great place, calming vibe, located in the middle of everything you may need. "
United States
Kim
Peaceful getaway convenient to local amenities including beach, boating & food

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (240 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Edgewater
10.0 out of 10, Exceptional, (225 reviews)
"Awesome location and very nice, we had a great stay! "
United States
Megan B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville
10.0 out of 10, Exceptional, (105 reviews)
"Great stay!"
United States
Scott L.
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (42 reviews)
"The guidebook binder at the property helpfully had details about the Soul Oasis, like how to operate the heaters and fireplace, and suggested local spots and restaurants to visit. Also, the kitchen conveniently had many pots and pans and tools. The view of the water was a highlight!"
United States
Bronwen C.
The price is AED 463
AED 1,012 total
includes taxes & fees
13 Apr - 14 Apr
Soul Oasis - home on the Chesapeake Bay

Cottage downtown on a quiet street

Cottage downtown on a quiet street
Downtown St. Michaels
9.8 out of 10, Exceptional, (59 reviews)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
United States
Casey G.
Cottage downtown on a quiet street

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.
Cape Saint Claire
10.0 out of 10, Exceptional, (103 reviews)
"We love our stay at the Firefly Cottage, our home away from home. "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (17 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AED 1,064
AED 1,984 total
includes taxes & fees
30 Mar - 31 Mar
Secluded Cozy Cottage in Historic Downtown

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.4 out of 10, Exceptional, (130 reviews)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
Royal Oak
Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Lovely 2-bedroom waterfront cottage in charming Wittman

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
10.0 out of 10, Exceptional, (1 review)
"I recently stayed at this lovely VRBO, and it exceeded my expectations in every way. From the moment I walked in, the home felt incredibly cozy and welcoming. Everything was spotless—truly one of the cleanest vacation rentals I’ve stayed in—which immediately set the tone for a relaxing visit.The space itself is bright and airy, with plenty of natural light that makes the home feel open and refreshing throughout the day. It’s thoughtfully furnished and had everything I needed for a comfortable...
United States
Mario V.
Lovely 2-bedroom waterfront cottage in charming Wittman

Your Annapolis Waterfront retreat - ready for a winter getaway!

Your Annapolis Waterfront retreat - ready for a winter getaway!
West Annapolis
10.0 out of 10, Exceptional, (89 reviews)
"Great location and a beautiful place, thanks Jim. "
United States
Michael M.
Your Annapolis Waterfront retreat - ready for a winter getaway!

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River
9.8 out of 10, Exceptional, (43 reviews)
"This was such a beautiful property right on the water! It was everything I wanted for a quiet weekend away. The host was quick to respond and full of great recommendations. I am definitely planning on staying here again and will recommend it to anyone else 10/10"
United States
Meghan G.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Saint Leonard
10.0 out of 10, Exceptional, (19 reviews)
"The house was very nice and had great amenities supplied by the owners. "
United States
Kenly
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
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