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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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

1. NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues

NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
Stevensville
10.0 out of 10, Exceptional, (11 reviews)
"Clean, comfortable and well appointed, set in a very scenic and relaxed location. This house suited our needs perfectly and we hope to rent it again same time next year."
United States
Dave D.
NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
An outdoor patio with two tables set up, surrounded by ivy-covered walls and string lights.

2. 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, (258 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!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

3. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.8 out of 10, Excellent, (9 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is CA $519
CA $763 total
includes taxes & fees
Aug 31 - Sep 1
Fabulous 5-bedroom house with AC in charming Annapolis
A building with a porch, a sign reading "Ristorante St. Michaels," and a brick sidewalk.

4. Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (11 reviews)
"Loved the walkable nature of this property"
United States
Melody E.
Grace Cottage, St Michaels Walk to everything!
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a stove.

5. Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Historic District
10.0 out of 10, Exceptional, (46 reviews)
"The perfect place to spend the day exploring all Annapolis has to offer. Within walking distance to all of downtown Annapolis nestled in a cute neighborhood. The home was well appointed, beds were amazingly comfortable and the home was clean and well maintained. We will definitely stay here again if we ever return to Annapolis. "
United States
Megan V.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

6. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $116
CA $377 total
includes taxes & fees
Aug 30 - Aug 31
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $168
CA $360 total
includes taxes & fees
Sep 2 - Sep 3
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious kitchen with a central island, wooden dining table, and chairs, along with a refrigerator and oven.

8. “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, (10 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.
A spacious living room with two green sofas, a coffee table, and a chandelier. Large windows offer a view of the sea and a pier.

9. Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing

Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing
Port Republic
10.0 out of 10, Exceptional, (137 reviews)
"Our family had a wonderful time! There was plenty of space for our family of 4. The house had everything we needed including spots to just relax and watch the waves inside the house. In the evening when the temps got cooler it was nice to be on the deck and watch the sunset. The kids could not get enough of the easy beach access. We found plenty of shark teeth and fossils! Alicia was so kind and easy to work with. Would love to rent again!"
United States
Valerie R. W.
Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing
A modern kitchen with white cabinets, stainless steel appliances, a central island, and a large wall clock.

10. Recently Renovated Annapolis Home - Conveniently Located

Recently Renovated Annapolis Home - Conveniently Located
Murray Hill
10.0 out of 10, Exceptional, (78 reviews)
"Right on a main road, extremely convenient location, nicely decorated, comfortable, clean."
United States
Sammy M.
Recently Renovated Annapolis Home - Conveniently Located
A two-story house with a white facade, blue shutters, and a wooden front door. There are flower boxes on the windowsills and a white picket fence in front.

11. Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Murray Hill
10.0 out of 10, Exceptional, (55 reviews)
"Our second time staying here- lovely as ever"
United States
Christine T.
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
A modern kitchen with white cabinetry, a stainless steel refrigerator, wooden shelves, and pendant lighting.

12. 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, (52 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
A modern kitchen with wooden cabinets, a built-in oven, and a dining area with a table and chairs.

13. Belle of the Chesapeake Bay

Belle of the Chesapeake Bay
Lusby
8.8 out of 10, Excellent, (26 reviews)
"Nice place. Good location"
United States
Brandon H.
Belle of the Chesapeake Bay
A sandy beach with a wooden jetty extending into calm waters.

14. Private Cottage on gated estate

Private Cottage on gated estate
Annapolis
9.8 out of 10, Exceptional, (36 reviews)
"Very good location. Our family enjoyed our stay. "
United States
Teresa R.
Private Cottage on gated estate
A lakeside view with chairs and a table, a rainbow, and trees.

15. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is CA $287
CA $496 total
includes taxes & fees
Aug 30 - Aug 31
Bright and airy waterfront getaway
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

16. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is CA $193
CA $467 total
includes taxes & fees
Sep 1 - Sep 2
Large 2 bedroom house with private parking in a nice neighborhood
A wooden deck with a table and chairs overlooking a calm body of water at sunset.

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

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis
10.0 out of 10, Exceptional, (33 reviews)
"Amazing views right on the water. Perfect home for a long weekend getaway "
United States
Thomas C.
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
A covered porch with a table set for dining, a rocking chair, and a ceiling fan.

18. Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels
Tilghman Island
9.6 out of 10, Exceptional, (16 reviews)
"Perfect place - clean, stocked, beautiful. We loved it and will be back."
United States
Kate
Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $147
CA $416 total
includes taxes & fees
Aug 31 - Sep 1
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

20. Bayfront Maryland Retreat w/ Deck, Near Beaches!

Bayfront Maryland Retreat w/ Deck, Near Beaches!
North Beach
9.4 out of 10, Exceptional, (16 reviews)
"Perfect cottage on the bay! Beautiful view. Love that it was close to Herrington Harbor but not too far from town. Host was very responsive. Great to place to stay."
United States
Suzanne
Bayfront Maryland Retreat w/ Deck, Near Beaches!
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

St Michaels Inn

St Michaels Inn

8/10 Good
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"
CYNTHIA 3-night trip
Posted 4 hours ago
St Michaels Inn

Find out more about Talbot County

Talbot County Vacation Homes information

Number of reviews
871
Accommodation
787 Vacation Homes
Lowest Price
CA $360
Highest Price
CA $763

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