We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Talbot County Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
44 rentals in Talbot County.
Sort by:
Tripadvisor Sort
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Payment Protection
5 other travelers have booked this property
Premier Cottage in St. Michaels- In Town Location!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
15 other travelers have booked this property
Location Location! St Michaels-- In Town Cottage!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
13 other travelers have booked this property
Main House at Grandview at Pleasure Point
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage 1a at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage 1b at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage 2 at Grandview Pleasure Point
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Pines: Enjoy Harris Creek w/Pool and Boats
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
7 other travelers have booked this property
RESTORED WATERFRONT COTTAGE
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
2 other travelers have booked this property
Historic Waterfront Property with Wi-Fi and Dock
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
3 other travelers have booked this property
Tranquil Easton Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Pot Pie House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
2 other travelers have booked this property
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
1 other traveler has booked this property
NewSt. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
*****Waterfront home w/ pool in St. Michaels
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Eastern Shore Getaway Near St. Michaels
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Hot Tub/Warming Hut, Screened Deck, Encl. Porch, Kayaks, Bikes, Fishing Poles
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
2 other travelers have booked this property
Waterview Cottage In St. Michaels!
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
7 other travelers have booked this property
St. Michael's Premier in Town Summer Cottage!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
1 other traveler has booked this property
St. Michaels Area Cottage - Walk to Water & Marina
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
1 other traveler has booked this property
St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Fully remodel 2 bedroom country cottage.
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
St. Michael's Waterfront Vacation Cottage
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Gorgeous Sunsets and Chesapeake Charm
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxurious Waterfront Kent Island Home 30 miles from Annapolis
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Comfy home on beautiful Leadenham Creek. Book now for summer!
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Shelter in place -15 ac estate while children go to school & you work online
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Elegant, Waterfront Cottage on Six Acres in Historic Area
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Tidewater home between Easton & ST Michaels!
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Anchorage B&B - Skipjack
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Relax or Play on the Choptank River!
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
4 bedroom Bed and Breakfast on the Choptank River
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming 3 Bedroom 3 Bath Beach Front Property
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Private waterfront estate with pool, convenient to Easton and St. Michaels
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1