Vacation rentals in Talbot County

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Top cities to explore in Talbot County

St. Michaels

Vacation Rentals
St. Michaels

Top vacation rentals in Talbot County

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

7.92 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

7.96 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

7.91 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

4.29 mi from city center
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This vacation home features an outdoor pool and a sauna. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Kitchen
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

8.02 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

14.29 mi from city center
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This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.
Pool
Kitchen
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

26.62 mi from city center
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A gym is featured at this vacation home, along with limo/town car service and a garden. Laundry facilities, concierge services, and barbecue grills are also on offer.
Pool
Kitchen
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

17.04 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
18.29 mi from city center
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This houseboat features barbecue grills.
Kitchen
Pet friendly
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

25.94 mi from city center
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This vacation home features an outdoor pool and a hot tub. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

21.72 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

29.36 mi from city center
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A garden is available at this cabin.
Pool
Kitchen
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

24.87 mi from city center
$315 nightly
The price is $338 total per night
$338 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this vacation home in Edgewater. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Sand Point Marsh and Triton Beach are located nearby.
Washer
Dryer
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

16.27 mi from city center
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Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Kitchen
Free WiFi
Charming townhome with AC and WiFi in delightful Annapolis

Charming townhome with AC and WiFi in delightful Annapolis

26.83 mi from city center
$68 nightly
The price is $77 total per night
$77 total
Nov 4 - Nov 5
Total with taxes and fees
This vacation home features laundry facilities.
Free WiFi
Air conditioning
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

17.29 mi from city center
$257 nightly
The price is $273 total per night
$273 total
Oct 19 - Oct 20
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

26.34 mi from city center
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This vacation home features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Hot Tub
Washer
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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

26.43 mi from city center
$258 nightly
The price is $285 total per night
$285 total
Oct 14 - Oct 15
Total with taxes and fees
This apartment features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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.

The Best Way to Find Vacation Rentals in Talbot County 

How cheap is a vacation rental in Talbot County?


You can find Talbot County vacation rentals from just $77 per night. 


How do you look for the best vacation rental deals in Talbot County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Talbot County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Talbot County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Talbot County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Talbot County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Talbot County?


Whether you’re a winter wanderer or planning a summer sojourn, Talbot County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Talbot County?


Take your pick from the excitement of the big Talbot County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Talbot County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Talbot County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.