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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Top Cities in Talbot County

Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay
CottagesCottages

St. Michaels

St. Michaels

Our top choices for Talbot County cottages

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (49 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
$259 nightly
The price is $274
May 26 - May 27
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (244 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

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
Exterior

"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, (17 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
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
$238 nightly
The price is $263
May 27 - May 28
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Property grounds

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (50 reviews)
"We love this place!"
United States
Joan K.
$306 nightly
The price is $324
May 27 - May 28
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior

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, (127 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveler
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

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
9.6 out of 10, Exceptional, (48 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.
Exterior

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
9.6 out of 10, Exceptional, (131 reviews)
"Our dog was so comfortable and welcome at this rental!"
United States
Kathie F.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman Island
10.0 out of 10, Exceptional, (15 reviews)
"Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery "
United States
David M.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
9.8 out of 10, Exceptional, (41 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior detail

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
North Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior

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, (202 reviews)
"Perfect house close to St Michael’s attractions"
United States
Carolyn E.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds

Firefly Cottage at the Cape, Hot Tub, Community beach, Strawberry festival, USNA

Firefly Cottage at the Cape, Hot Tub, Community beach, Strawberry festival, USNA
Cape Saint Claire
10.0 out of 10, Exceptional, (107 reviews)
"We love our stay at the Firefly Cottage, our home away from home. "
United States
Debbie Y.
Firefly Cottage at the Cape, Hot Tub, Community beach, Strawberry festival, USNA
Exterior

Eastern Shore beach cottage get-away

Eastern Shore beach cottage get-away
Rock Hall
10.0 out of 10, Exceptional, (139 reviews)
"Host seemed welcoming."
United States
Deborah G.
Eastern Shore beach cottage get-away
Exterior

Cozy, unique, historic registered cottage on the Corsica River!

Cozy, unique, historic registered cottage on the Corsica River!
Centreville
10.0 out of 10, Exceptional, (7 reviews)
"Lovely property, cool history beautiful decor"
United States
Christine C.
Cozy, unique, historic registered cottage on the Corsica River!
Exterior

Now available for USNA Commissioning Week! 16-22 May. Easy walk to Stadium. <br>Your Annapolis Waterfront retreat for a weekend getaway.

Now available for USNA Commissioning Week! 16-22 May. Easy walk to Stadium. <br>Your Annapolis Waterfront retreat for a weekend getaway.
West Annapolis
10.0 out of 10, Exceptional, (89 reviews)
"Great location and a beautiful place, thanks Jim. "
United States
Michael M.
Now available for USNA Commissioning Week! 16-22 May. Easy walk to Stadium. <br>Your Annapolis Waterfront retreat for a weekend getaway.
Outdoor dining

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, (20 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
Beach towels

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, cozy, and charming. Loved the location! "
United States
Joshua K.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Exterior

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, (120 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
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
"The Graduate is an amazing hotel. My favorite part was the attentiveness of the staff, the nostalgic USNA decor, and the greeting of hot chocolate during an unexpected cold and rainy day in May!"
Kimberly 5-night trip
Posted 3 hours ago
Graduate by Hilton Annapolis

Find out more about Talbot County

Talbot County Cottages information

Number of reviews
1,530
Accommodation
127 Cottages
Lowest Price
$263
Highest Price
$324

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