A stone church with a pointed steeple and arched windows.

Vacation Rentals in Talbot County

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Top Cities in Talbot County

Our top choices for Talbot County vacation rentals

1. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
$164 nightly
The price is $174
Aug 16 - Aug 17
Total with taxes and fees
Pet-Friendly Pond Cottage • Nature Escape Near Beaches

2. 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, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$316 nightly
The price is $343
Aug 24 - Aug 25
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Aug 12 - Aug 13
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (45 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
$270 nightly
The price is $292
Aug 13 - Aug 14
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

5. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
$240 nightly
The price is $254
Aug 13 - Aug 14
Total with taxes and fees
Sailwinds Loft at Cambridge Creek

6. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Lovely ! "
United States
Ellen B.
$301 nightly
The price is $333
Aug 13 - Aug 14
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away

7. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$268 nightly
The price is $296
Aug 23 - Aug 24
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

8. Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
$255 nightly
The price is $270
Aug 17 - Aug 18
Total with taxes and fees
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

9. Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very Good, (9 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
$372 nightly
The price is $394
Aug 26 - Aug 27
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

10. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$267 nightly
The price is $304
Aug 18 - Aug 19
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

11. 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, (24 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
$492 nightly
The price is $522
Sep 8 - Sep 9
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

12. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
$285 nightly
The price is $303
Sep 8 - Sep 9
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

13. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
$406 nightly
The price is $463
Aug 24 - Aug 25
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

14. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$425 nightly
The price is $485
Aug 12 - Aug 13
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

15. 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, (15 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
$400 nightly
The price is $424
Aug 12 - Aug 13
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

16. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
$254 nightly
The price is $269
Aug 17 - Aug 18
Total with taxes and fees
Waterfront Getaway with Dock

17. 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, (5 reviews)
$261 nightly
The price is $277
Aug 31 - Sep 1
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

18. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$260 nightly
The price is $276
Aug 16 - Aug 17
Total with taxes and fees
BAYSIDE BUNGALOW

19. 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.
$296 nightly
The price is $337
Sep 2 - Sep 3
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

20. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$272 nightly
The price is $282
Aug 19 - Aug 20
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
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

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 $343 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.