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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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, (46 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.
$260 nightly
The price is $275
May 6 - May 7
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, (243 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
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
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

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)
"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!
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
9.8 out of 10, Exceptional, (44 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.
Property grounds

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
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
9.4 out of 10, Exceptional, (130 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

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
9.8 out of 10, Exceptional, (39 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
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.
$243 nightly
The price is $268
May 5 - May 6
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Outdoor dining

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
Property grounds

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA
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, hot tub, USNA
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 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.
$657 nightly
The price is $749
May 5 - May 6
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior

The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (170 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
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, (13 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

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, (201 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
Exterior

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Deale
9.8 out of 10, Exceptional, (84 reviews)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
United States
Paul M.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Terrace/patio

3 bedroom, waterfront cottage on the shores of the Chesapeake Bay.

3 bedroom, waterfront cottage on the shores of the Chesapeake Bay.
North Beach
8.0 out of 10, Very Good, (1 review)
"Wonderful weekend with friends and family, plenty to do in Chesapeake Beach and really beautiful views from the home. The property is in an excellent location, and parking was easy although I imagine it might get tough for more than one car to find close parking during the summer months. Walking distance to shops, restaurants, ice cream, etc. (Many are literally steps away) The home has everything you need, and the couches were really comfortable! Overall the property could probably use a little...
United States
Nic R.
3 bedroom, waterfront cottage on the shores of the Chesapeake Bay.
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
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

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

10/10 Excellent
"Everything about this hotel was excellent and I would highly recommend staying here"
David 1-night trip
Posted 5 hours ago
Best Western Plus Easton Inn & Suites

Find out more about Talbot County

Talbot County Cottages information

Number of reviews
1,409
Accommodation
127 Cottages
Lowest Price
$268
Highest Price
$749

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