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In two months
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Mar 27 - Mar 29

Top Cities in Talbot County

CottagesCottages

St. Michaels

St. Michaels

Cottages in Talbot County

Microwave, oven, stovetop, dishwasher
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.

2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$261 nightly
The price is $277
Dec 6 - Dec 7
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
9.8 out of 10, Exceptional, (236)
"Perfect setting! Close to St. Michaels and Tilghman Very comfortable cottage, would recommend! "
United States
michele m.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior
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, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (38)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$252 nightly
The price is $267
Dec 8 - Dec 9
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Property grounds
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!

Saint Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Outdoor dining
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Neavitt
9.8 out of 10, Exceptional, (56)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
United States
Michael
The Middle Point Cabin in Saint Michaels
Exterior
Charming Waterfront Cottage Retreat near St. Michaels

Charming Waterfront Cottage Retreat near St. Michaels

Bozman
10.0 out of 10, Exceptional, (10)
"My husband and I were delighted to stay in this beautiful home located on the most picturesque property for our 30th wedding anniversary. From the design of the house to the small details within it, making it feel like a home away from home, everything was perfect. We will stay here again should we revisit this area! "
United States
Jennifer F.
Charming Waterfront Cottage Retreat near St. Michaels
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (265)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Outdoor dining
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District
9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$627 nightly
The price is $714
Jan 3 - Jan 4, 2026
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
Exterior
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Hillsmere
10.0 out of 10, Exceptional, (170)
"Love the decor, the comfort and vibe of the place. Wish I had stayed longer! "
United States
Lauren m.
The Yellow Cottage on Harness Creek
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 8 - Dec 9
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Fridge, microwave, oven, stovetop
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)
"Incredible property and stay."
United States
Hunter B.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Exterior
Firefly Cottage at the Cape, Community beach, Hot tub, USNA vs Army game, pets

Firefly Cottage at the Cape, Community beach, Hot tub, USNA vs Army game, pets

Cape Saint Claire
10.0 out of 10, Exceptional, (101)
"Another fabulous stay at the Firefly Cottage "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA vs Army game, pets
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Epping Forest
9.8 out of 10, Exceptional, (30)
"We so enjoyed our time at the cottage. Isaac was so helpful and responsive when we had questions. The cottage had everything we needed or wanted and we had a lovely, restful long weekend here with our daughter. What a great cottage in a great location, close to things we needed, but nestled in the woods and on the water. We will be back! Highly recommend. "
United States
M G.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Exterior
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Churchton
9.8 out of 10, Exceptional, (82)
"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
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, (18)
"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
Interior
6 Mi to Dtwn: Family-friendly Home in Annapolis!

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

3.0 star property
Annapolis
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Outdoor spa tub
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cambridge
10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
United States
Deirdre G.
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
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
"Very nice hotel. The dog park could have better lighting. "
Andrew 1-night trip
Posted 2 days ago
Graduate by Hilton Annapolis

Find out more about Talbot County

Talbot County Cottages information

Number of reviews
1,322
Accommodation
131 Cottages
Lowest Price
$267
Highest Price
$885

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