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Vacation Rentals in Talbot County

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Top Vacation Rentals in Talbot County

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

Cottage in St Michaels

9.6 out of 10, Exceptional, (126)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in St Michaels

9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Fridge, microwave, oven, stovetop
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Vacation Home in Royal Oak

10.0 out of 10, Exceptional, (90)
"5 out of 5. Beautiful, well kept property across aspects. Comfortably accommodated our group of 14. Excellent communication with the Renter and felt as though we were borrowing the property from a family friend. Would recommend to anyone!"
United States
Katie M.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Vacation Home in Easton

10.0 out of 10, Exceptional, (96)
"Overall the stay was very good."
United States
Gregg S.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Vacation Home in Stevensville

10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Vacation Home in Cambridge

10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Vacation Home in Historic District

9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is ￥100,943
￥184,046 total
includes taxes & fees
Dec 8 - Dec 9
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Vacation Home in Tracys Landing

9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Vacation Home in stevensville

10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Vacation Home in Cambridge

9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Vacation Home in Chester

10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,066
￥46,925 total
includes taxes & fees
Jan 2 - Jan 3, 2026
BAYSIDE BUNGALOW
Exterior
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Vacation Home in Murray Hill

2.5 star property
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,358
￥24,641 total
includes taxes & fees
Dec 9 - Dec 10
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Vacation Home in Edgewater

9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is ￥46,133
￥110,904 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Edgewater/Mayo Gateaway w/ Hot Tub
Dining
Million Dollar View of the Chesapeake Bay

Vacation Home in Deale

9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of 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

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

10/10 Excellent
"Everything was great, clean and pretty quiet."
Gregory 1-night trip
Posted 2 days ago
Best Western Plus Easton Inn & Suites

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Vacation Apartments in Talbot County

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