Talbot County Vacation Rentals

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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
Vacation HomesVacation Homes

St. Michaels

St. Michaels

Our top choices for Talbot County vacation homes

Exterior

PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history
Historic District
10.0 out of 10, Exceptional, (223 reviews)
"We had a great time here. It is so close to downtown and USNA. The comfort and convenience is terrific. "
United States
Amy B.
PERFECT LOCATION in the heart of history
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $275
CA $415 total
includes taxes & fees
May 24 - May 25
BAYSIDE BUNGALOW
Property grounds

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Tilghman Island
10.0 out of 10, Exceptional, (39 reviews)
"We love this property and most definitely plan to stay there again in the future."
United States
Joe F.
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Fridge, microwave, oven, stovetop

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.8 out of 10, Exceptional, (21 reviews)
"Super nice and very clean, perfect for our stay."
United States
Douglas S.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Fridge, microwave, oven, stovetop

"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Amazing bayfront views! Lots of great restaurants and boutique shopping nearby. "
United States
Karen G.
"La Licorne" Waterfront Beach Cottage
Interior

Charming Historic Annapolis Home With Two Off-street Parking Places!

Charming Historic Annapolis Home With Two Off-street Parking Places!
Historic District
10.0 out of 10, Exceptional, (208 reviews)
"Wonderful weekend in a great location! House was perfect for 3 couples looking to get away for the weekend"
United States
Barb K.
Charming Historic Annapolis Home With Two Off-street Parking Places!
Smart TV, fireplace

Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
8.0 out of 10, Very good, (3 reviews)
"House was clean and up to date. Pool and location were perfect."
United States
Emily K.
The price is CA $1,375
CA $1,664 total
includes taxes & fees
May 25 - May 26
Kent Island Luxary Home W/ Pool and walking distance from the beach
Exterior

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, (44 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 CA $220
CA $497 total
includes taxes & fees
Jun 2 - Jun 3
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV, fireplace, video games, books

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side
9.8 out of 10, Exceptional, (29 reviews)
"Very cute house. We had a wonderful weekend! "
United States
Kimberly B.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Property grounds

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, (134 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
Beach nearby, sun loungers, beach towels

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes
North Beach
10.0 out of 10, Exceptional, (84 reviews)
"Host was wonderful. Place was amazing. We could walk to a lot of restaurants, a brewery, breakfast spot and of course the pier! We will stay here again. "
United States
John B.
The Blue Crab Beach House - Free beach passes
Smart TV, fireplace

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Lusby
10.0 out of 10, Exceptional, (69 reviews)
"Great home base to explore nearby beaches."
United States
Lisa K.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
8.6 out of 10, Excellent, (8 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is CA $309
CA $494 total
includes taxes & fees
May 25 - May 26
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Interior

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
St. Michaels
8.0 out of 10, Very good, (2 reviews)
"Very relaxing"
United States
Andrew K.
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Interior

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
Easton
10.0 out of 10, Exceptional, (4 reviews)
"I had a wonderful stay while on a work trip to Easton. The house is super cute with a lot of very thoughtful touches, everything from phone charges and cleaning supplies to snacks and toiletries. I would highly recommend this stay to anyone looking to travel to the area. "
United States
amy p.
“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
Outdoor dining

Back Creek Villa Covered Deck

Back Creek Villa Covered Deck
Solomons
9.0 out of 10, Wonderful, (2 reviews)
"Love that they accept pets location is great and the food in the area was great . Just one suggestion since there is no central air conditioning I would install a window unit in the master bed room with no ceiling fan in the room it was stuffy and it wasn’t really hot but other then that place is perfect "
United States
Anthony C.
Back Creek Villa Covered Deck
Property grounds

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
Smart TV

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Everything was great."
United States
Brandon H.
4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
Beach nearby

NEW! Charming Farm House in Historic Kent Island

NEW! Charming Farm House in Historic Kent Island
Stevensville
9.0 out of 10, Wonderful, (16 reviews)
"My family stayed in this lovingly restored farm house. The owner provided the perfect binder full of information to acquaint us to our surroundings and was very responsive to our needs and inquiries. Wish we had more time to explore. Will return!"
United States
Carlos and Delia S.
NEW! Charming Farm House in Historic Kent Island
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
The price is CA $371
CA $823 total
includes taxes & fees
May 26 - May 27
Charming Annapolis WaterVIEW Home
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4/10 Poor
"Staff was just okay. Not super welcoming. The hotel is older and just not kept up well. The lobby and restaurant were nice enough but the room wasn’t up to Double Tree standards. My door wouldn’t seal closed, my bathroom door wouldn’t even close shut all the way it was too big for the door frame, there was mold on the ceiling and the pillows smelled moldy. I left a day early because I didn’t want to stay another night."
Kellee 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Talbot County

Talbot County Vacation Homes information

Number of reviews
744
Accommodation
805 Vacation Homes
Lowest Price
CA $415
Highest Price
CA $1,664

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