A stone church with a pointed steeple and arched windows.

Cottages in Talbot County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Top Cities in Talbot County

A waterfront street lined with trees and a white building with a balcony.
CottagesCottages

St. Michaels

St. Michaels
Two people in a red canoe on a body of water with a sunset and a bridge in the background.
CottagesCottages

Tilghman

Tilghman

Our top choices for Talbot County cottages

Exterior

1. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Annapolis
9.8 out of 10, Exceptional, (44 reviews)
"Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back."
United States
Brian R.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Exterior

2. 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, (137 reviews)
"Fantastic location, the host was quick to respond to questions. Would book again."
United States
Jim K.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

3. "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, (26 reviews)
"The views are an amazing. The cottage is well appointed. The hosts were responsive. It was an excellent trip"
United States
Paul H.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

4. 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, (208 reviews)
"Really nice cottage in the middle of everything. Loved the screened in porch and large den."
United States
greg b.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

5. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is AED 562
AED 1,168 total
includes taxes & fees
11 Sep - 12 Sep
Soul Oasis - home on the Chesapeake Bay
Outdoor dining

6. 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, (231 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

7. 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
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
The price is AED 592
AED 1,022 total
includes taxes & fees
11 Sep - 12 Sep
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

8. The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (179 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
Exterior

9. Waterfront Annapolis Cottage: Fire Pit & Pier

Waterfront Annapolis Cottage: Fire Pit & Pier
Annapolis
9.4 out of 10, Exceptional, (45 reviews)
"The place worked well for us. It must be a great place in the warmer months."
United States
John R.
Waterfront Annapolis Cottage: Fire Pit & Pier
Exterior

10. Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (274 reviews)
"Rob was such a wonderful and inviting host"
United States
Stacy S.
Family and Pet-Friendly, Waterfront with Pier
Exterior

11. Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful, private setting, but not far from the town of St. Michaels. House was very clean and beds were comfy. The kitchen was very well equipped for preparing meals. We really enjoyed relaxing in the screened in porch and on the Adirondack chairs overlooking the water. There was so much wildlife to view: bald eagles, herons, tree frogs, crabs…We had a great time! Thank you!"
United States
Melissa B.
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Outdoor dining

12. 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, (18 reviews)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining

13. 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, (22 reviews)
"All was great....loved the access to the little private beach with our little ones. Kitchen was clean and orderly and the living room was quaint."
United States
Kristin D.
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Exterior

14. 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, (132 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

15. Eastern Shore beach cottage get-away

Eastern Shore beach cottage get-away
Rock Hall
10.0 out of 10, Exceptional, (141 reviews)
"Great time, great property!"
United States
Madeline C.
Eastern Shore beach cottage get-away
Exterior

16. Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (254 reviews)
"The place was very clean and comfortable. Loved the view. Would definitely stay again."
United States
Susan E.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

17. Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
Exterior

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

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown St. Michaels
9.6 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Jody M.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior

19. 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, (19 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

20. Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!
North Beach
9.6 out of 10, Exceptional, (28 reviews)
"Cozy cottage, beds were comfy and it was great to bring our dog. "
United States
Chloe W.
Updated North Beach Cottage: Pet Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Talbot County Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Staff was lovely and the location can’t be beat. The Maryland Inn building is old, and some of the elements are thus seemingly harder to clean (ie if you’re weird about bathrooms being spotless, this one isn’t for you)."
Anya 2-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Explore a world of travel with Expedia