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

Three birds perched on a wooden structure by the water.

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

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
$1,127 nightly
The price is $1,247
Sep 29 - Sep 30
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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!

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.
$1,074 nightly
The price is $1,188
Sep 29 - Sep 30
Total with taxes and fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
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

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
$595 nightly
The price is $631
Sep 29 - Sep 30
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

4. 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.
$230 nightly
The price is $244
Sep 29 - Sep 30
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
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 29 - Sep 30
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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

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.
$543 nightly
The price is $576
Sep 29 - Sep 30
Total with taxes and fees
Turnbridge Manor
A building with a gabled roof and a circular vent on the roof.

7. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$271 nightly
The price is $300
Sep 29 - Sep 30
Total with taxes and fees
BAYSIDE BUNGALOW
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

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.
$310 nightly
The price is $329
Sep 29 - Sep 30
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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

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.
$555 nightly
The price is $588
Oct 5 - Oct 6
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A modern exterior with a black door, a metal staircase, and a lantern.

10. 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.
Cass-Away Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

11. 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.
$240 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
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

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.
$932 nightly
The price is $988
Sep 30 - Oct 1
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

13. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (126 reviews)
"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.)"
United States
Charr
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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!

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.
$240 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A bedroom with a bed, a dresser, a mirror, and a window with curtains.

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

More, than just a place to sleep - welcome home!
Cambridge
$352 nightly
The price is $390
Sep 29 - Sep 30
Total with taxes and fees
More, than just a place to sleep - welcome home!
A kitchen with wooden cabinets, a dining table, and a refrigerator.

16. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
$250 nightly
The price is $276
Sep 29 - Sep 30
Total with taxes and fees
Family Retreat at Lansdowne Manor
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

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$1,062 nightly
The price is $1,179
Sep 29 - Sep 30
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
A beach with chairs and a pier in the background.

18. 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.
$384 nightly
The price is $437
Sep 29 - Sep 30
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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
$332 nightly
The price is $352
Oct 27 - Oct 28
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
$570 nightly
The price is $650
Sep 29 - Sep 30
Total with taxes and fees
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

Sonesta ES Suites Annapolis

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."
kelly 2-night trip
Posted 14 hours ago
Sonesta ES Suites 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 $258 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?


Vacation rentals in Talbot County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Talbot County vacation rentals to suit everyone. 


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.