Talbot County Holiday Rentals from €274: Search Short-Term Rentals

A stone church with a pointed steeple and arched windows.

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Top Cities in Talbot County

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

Our top choices for Talbot County holiday rentals

Three birds perched on a wooden structure by the water.

1. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

barbara s.

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

2. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

includes taxes & fees

5 Oct - 6 Oct

A wooden interior with a dining area, sofas, and a table.

3. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge

Anonymous traveller

includes taxes & fees

30 Sept - 1 Oct

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

4. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

includes taxes & fees

30 Sept - 1 Oct

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

5. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

6. Turnbridge Manor

Denton

Glenn S.

includes taxes & fees

30 Sept - 1 Oct

A building with a gabled roof and a circular vent on the roof.

7. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

5 Oct - 6 Oct

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

8. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

includes taxes & fees

12 Oct - 13 Oct

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

9. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

includes taxes & fees

30 Sept - 1 Oct

A modern exterior with a black door, a metal staircase, and a lantern.

10. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michelle P.

includes taxes & fees

12 Oct - 13 Oct

A two-story house with a red roof, a brick chimney, and a small porch.

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

includes taxes & fees

3 Oct - 4 Oct

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

13. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

30 Sept - 1 Oct

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Dawn G.

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bed, a dresser, a mirror, and a window with curtains.

15. More, than just a place to sleep - welcome home!

Cambridge

includes taxes & fees

30 Sept - 1 Oct

A kitchen with wooden cabinets, a dining table, and a refrigerator.

16. Family Retreat at Lansdowne Manor

Centreville

Emily C.

includes taxes & fees

30 Sept - 1 Oct

A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

17. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

includes taxes & fees

12 Oct - 13 Oct

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Sharon Z.

includes taxes & fees

30 Sept - 1 Oct

19. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Robert

includes taxes & fees

27 Oct - 28 Oct

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

20. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

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Top Talbot County Hotel Reviews

Courtyard by Marriott Annapolis

10/10 Excellent

"The staff were super friendly."

Sonesta ES Suites Annapolis

10/10 Excellent

"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."

Find out more about Talbot County

Holiday Homes in Talbot County

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Room 1

Change your mind

Treat yourself

Be picky

Top Cities in Talbot County

St. Michaels

Our top choices for Talbot County holiday rentals

1. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

2. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!