A stone church with a pointed steeple and arched windows.

Vacation Rentals in Talbot County

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Top Cities in Talbot County

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

St. Michaels

St. Michaels

Our top choices for Talbot County vacation rentals

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

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
$239 nightly
The price is $253
Sep 28 - Sep 29
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$547 nightly
The price is $580
Oct 27 - Oct 28
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$267 nightly
The price is $288
Sep 28 - Sep 29
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
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.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
$452 nightly
The price is $479
Sep 28 - Sep 29
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
$255 nightly
The price is $275
Sep 28 - Sep 29
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
$350 nightly
The price is $371
Sep 28 - Sep 29
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A modern exterior with a black door, a metal staircase, and a lantern.

8. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
$260 nightly
The price is $288
Sep 28 - Sep 29
Total with taxes and fees
Cass-Away Luxury Houseboat
A beach with chairs and a pier in the background.

9. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
$403 nightly
The price is $459
Sep 28 - Sep 29
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A two-story house with a red roof, a brick chimney, and a small porch.

10. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.0 out of 10, Very good, (5 reviews)
"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...
United States
Suzanne R.
$939 nightly
The price is $995
Sep 27 - Sep 28
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A building with a gabled roof and a circular vent on the roof.

11. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$271 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
BAYSIDE BUNGALOW
A modern kitchen with dark cabinets, a white countertop, and a large window.

12. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
$235 nightly
The price is $260
Oct 8 - Oct 9
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
$1,241 nightly
The price is $1,373
Sep 27 - Sep 28
Total with taxes and fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
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.

14. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Sep 28 - Sep 29
Total with taxes and fees
Turnbridge Manor
A wooden interior with a dining area, sofas, and a table.

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

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
$643 nightly
The price is $682
Sep 27 - Sep 28
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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.

16. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$1,068 nightly
The price is $1,185
Sep 28 - Sep 29
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

17. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
$393 nightly
The price is $433
Sep 27 - Sep 28
Total with taxes and fees
Sunset Breezes - quiet waterfront retreat
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

18. 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, (41 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.
$280 nightly
The price is $319
Sep 30 - Oct 1
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
$351 nightly
The price is $372
Oct 27 - Oct 28
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

20. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
$265 nightly
The price is $281
Oct 27 - Oct 28
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The room was perfect. The location was amazing!"
Nicole 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Talbot County

Discover your perfect Talbot County vacation rental with Expedia

How many vacation rentals are available in Talbot County?


Expedia has plenty of vacation rentals to choose from in and around  Talbot County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Talbot County?


The selection of Talbot County vacation rentals we have selected for you start as low as $275 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Talbot County?


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Why should I choose a vacation rental in Talbot County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Talbot County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Talbot County?


Find vacation rentals in Talbot County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Talbot County.  


What amenities are available in a vacation rental in Talbot County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Talbot County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Talbot County?   


Everytime is a great time to head to Talbot County! Staying in a Talbot County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Talbot County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Talbot County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Talbot County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Talbot County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.