A stone church with a pointed steeple and arched windows.

Talbot County Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Talbot County

A waterfront street lined with trees and a white building with a balcony.
Vacation HomesVacation Homes

St. Michaels

St. Michaels

Our top choices for Talbot County vacation homes

A beach with chairs and a pier in the background.

1. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $270
CA $671 total
includes taxes & fees
Oct 20 - Oct 21
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A room with a fireplace, a mirror, a wreath, and a potted plant.

2. Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Historic District
9.4 out of 10, Exceptional, (22 reviews)
"Good location convenient to old town Annapolis and even can walk there"
United States
Thomas B.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
A living room with a sofa, a wooden coffee table, a red chair, a white cabinet with glass doors, and a chandelier.

3. Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (70 reviews)
"Centrally located, this little dollhouse is perfect for a couple or small family. Easily in walking distance to all important locations in St Michael’s. The A/C works great too!"
United States
Bonnie T.
Dollhouse in Central Historic St Michaels
A large house with a swimming pool, deck chairs, and a covered patio area.

4. Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge
9.6 out of 10, Exceptional, (98 reviews)
"The host, Virgina, was amazing, so accommodating. Beautiful property. Looking forward to hopefully booking next year. "
United States
Susan B.
Private 2 Acre Waterfront Family Retreat with Pool & Pier
A modern kitchen with white cabinetry, a stainless steel refrigerator, wooden shelves, and pendant lighting.

5. 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, (56 reviews)
"Place was awesome and Erin, the property manager, was so kind"
United Kingdom
Carter S.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
An outdoor patio with two tables set up, surrounded by ivy-covered walls and string lights.

6. 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, (263 reviews)
"Great location in downtown Annapolis! House was clean and comfortable. We had a great stay."
United States
Kristen P.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

7. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $169
CA $369 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A wooden dock leading to a house with multiple windows and a well-lit interior.

8. Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Easton
10.0 out of 10, Exceptional, (113 reviews)
"Spectacular property...we can't wait to come back again next year!!"
United States
Matthew P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
A building with a porch, a sign reading "Ristorante St. Michaels," and a brick sidewalk.

9. Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (16 reviews)
"Loved the walkable nature of this property"
United States
Melody E.
Grace Cottage, St Michaels Walk to everything!
A two-story house with a covered patio and a swimming pool.

10. Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Greensboro
10.0 out of 10, Exceptional, (70 reviews)
"Had a great stay. Excellent property, beautiful location, perfect fenced yard for our dogs and lovely hosts. 100% recommend."
United States
Kirsty D.
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
A wooden deck with a table and chairs overlooking a calm body of water at sunset.

11. Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis
9.8 out of 10, Exceptional, (38 reviews)
"Beautiful property. Very clean with all the conveniences. Hosts have literally thought of everything...from sunscreen and bug spray to cell phone chargers and extension cords. Lots of comfortable seating indoors and outdoors. It was perfect for our small team retreat!"
United States
Shannon R.
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
A dining area with a large table and benches, a view of the sea through large windows, and a ceiling with recessed lighting.

12. One-Level Bayfront Home w Private Beach Access & Panoramic Chesapeake Bay Bridge Views

One-Level Bayfront Home w Private Beach Access & Panoramic Chesapeake Bay Bridge Views
Stevensville
9.8 out of 10, Exceptional, (27 reviews)
"This house is in a great location for myself and my friends. Would love to visit again."
United States
Kathy H.
One-Level Bayfront Home w Private Beach Access & Panoramic Chesapeake Bay Bridge Views
A modern kitchen with white cabinetry, a central island, and a dining area with two chairs.

13. Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels
Downtown St. Michaels
10.0 out of 10, Exceptional, (17 reviews)
"Excellent stay for two adults and a toddler. Super clean and comfortable. Great location on a quiet street, walkable to everything!"
United States
Jacqui Z.
Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels
Community Beach one block from Hickory House

14. Welcome to Hickory House on the Chesapeake Bay!

Welcome to Hickory House on the Chesapeake Bay!
Saint Leonard
9.6 out of 10, Exceptional, (22 reviews)
"Very clean had everything I needed host was very nice"
United States
BETZAIDA V.
Welcome to Hickory House on the Chesapeake Bay!
A room with large windows overlooking a snowy landscape and a body of water at sunset.

15. Home by the Bay: Chesapeake Bay Western Shore

Home by the Bay: Chesapeake Bay Western Shore
Port Republic
9.8 out of 10, Exceptional, (12 reviews)
"Such a perfect house and location! We will absolutely be back! "
United States
Tiana O.
Home by the Bay: Chesapeake Bay Western Shore
A sandy beach with trees and a clear blue sky.

16. 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, (8 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
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

17. Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (22 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
The price is CA $417
CA $682 total
includes taxes & fees
Nov 10 - Nov 11
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

18. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
The price is CA $320
CA $616 total
includes taxes & fees
Oct 15 - Oct 16
Rose Haven Coastal Cottage
A spacious living room with a large window, a round coffee table, and a grey armchair.

19. 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, (25 reviews)
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
A sandy beach with a wooden jetty extending into calm waters.

20. Private Cottage on gated estate

Private Cottage on gated estate
Annapolis
9.8 out of 10, Exceptional, (38 reviews)
"Very good location. Our family enjoyed our stay. "
United States
Teresa R.
Private Cottage on gated estate
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

Sandaway Suites & Beach

Sandaway Suites & Beach

10/10 Excellent
"This place is amazing! Ben went way over and above with hospitality. He has what he calls 7 o’clock coffee where he delivers coffee and pastries on your doorstep. Who does this? No one. The view of the bay is incredible. Will definitely stay again longer next time."
don 1-night trip
Posted 7 hours ago
Sandaway Suites & Beach

Find out more about Talbot County

Talbot County Vacation Homes information

Number of reviews
890
Accommodation
794 Vacation Homes
Lowest Price
CA $369
Highest Price
CA $682

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