A stone church with a pointed steeple and arched windows.

Vacation Homes in Talbot County

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Our top choices for Talbot County vacation homes

Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The house was adorable, very clean, and perfectly located right in downtown, which made it so easy to walk to everything. It had everything we needed and felt very comfortable. We would absolutely stay here again!"
United States
Tarah B.
Grace Cottage, St Michaels Walk to everything!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic District
10.0 out of 10, Exceptional, (249 reviews)
"Perfect location and lovely place for a weekend getaway!"
United States
Krista L.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is AED 1,587
AED 2,973 total
includes taxes & fees
30 Jun - 1 Jul
Charming Annapolis WaterVIEW Home

Private Pool & Stunning Bay Views on Kent Island

Private Pool & Stunning Bay Views on Kent Island
Stevensville
9.2 out of 10, Wonderful, (28 reviews)
"Great time at a nice place and location."
United States
Michael S.
Private Pool & Stunning Bay Views on Kent Island

Waterfront Home with Private Dock, Community Beach

Waterfront Home with Private Dock, Community Beach
Oyster Harbor
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay. Delightful property. Great hosts. Scenic, comfortable and near Annapolis!"
United States
Michele R.
Waterfront Home with Private Dock, Community Beach

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
Stevensville
9.8 out of 10, Exceptional, (22 reviews)
"Wonderful location, very well maintained and appointed. "
United States
Katrina D.
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
3-bedroom house in Deale located on Bay many amenities and great views

Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
9.8 out of 10, Exceptional, (62 reviews)
"What a stunning place, we were delighted by this 300 year old property, the view was incredible. "
United States
Karen N.
Circa 1700 Chesapeake Colonial home on the National Register.

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AED 316
AED 974 total
includes taxes & fees
28 Jun - 29 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cape Saint Claire
9.8 out of 10, Exceptional, (48 reviews)
"Everything was perfect for a large family gathering over the holiday. "
United States
daniel h.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge
9.8 out of 10, Exceptional, (135 reviews)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (31 reviews)
"The house was spacious and comfortable, a great fit for our work trip."
United States
Katie B.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Coastal Retreat Near Solomon’s Island, Water View & Semi-Private Beach, Sleeps 6

Coastal Retreat Near Solomon’s Island, Water View & Semi-Private Beach, Sleeps 6
Lusby
9.0 out of 10, Wonderful, (2 reviews)
"Had a nice time, the property was large and great for a family and pets. Loved the beach, close and easy to walk to. The host was easy to communicate with and accommodating. Pet-friendly and family-friendly"
United States
Tammy F.
Coastal Retreat Near Solomon’s Island, Water View & Semi-Private Beach, Sleeps 6

Pet Friendly-newly built house in peaceful beach community, located in Riva MD.

Pet Friendly-newly built house in peaceful beach community, located in Riva MD.
Riva
10.0 out of 10, Exceptional, (2 reviews)
"The place was amazing!"
United States
Sonya N.
Pet Friendly-newly built house in peaceful beach community, located in Riva MD.

Discover tranquility near Calvert Cliffs

Discover tranquility near Calvert Cliffs
Saint Leonard
9.8 out of 10, Exceptional, (20 reviews)
"Comfortable beds, large house with awesome views…had a great experience"
United States
Deborah R.
Discover tranquility near Calvert Cliffs

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Mechanicsville
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful house! The stay made me feel like I was home and very clean !"
United States
Jessica H.
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Eastport Cottage .5 mi from Downtown Annapolis

Eastport Cottage .5 mi from Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (59 reviews)
"Great stay - great location"
United States
Taliesin D.
Eastport Cottage .5 mi from Downtown Annapolis

Belle of the Chesapeake Bay

Belle of the Chesapeake Bay
Lusby
9.0 out of 10, Wonderful, (23 reviews)
"Nice place. Good location"
United States
Brandon H.
Belle of the Chesapeake Bay

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is AED 356
AED 1,038 total
includes taxes & fees
29 Jun - 30 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (61 reviews)
"Host was aces….place was great and right in the heart of town "
United States
Sean T.
Dollhouse in Central Historic St Michaels
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