Talbot County Holiday Rentals

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Our top choices for Talbot County holiday rentals

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

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

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

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown 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)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
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)
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cape Saint Claire
10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
Stevensville
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
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Historic District
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop
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.

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

Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
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
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
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!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is HK$4,918
HK$9,041 total
includes taxes & fees
14 Dec - 15 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

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

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
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!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
10.0 out of 10, Exceptional, (126)
"Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.."
United States
Karen K.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
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
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!
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!
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,401
HK$2,104 total
includes taxes & fees
4 Jan - 5 Jan 2026
BAYSIDE BUNGALOW
Exterior
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
2.5 star property
Murray Hill
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

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$770
HK$1,236 total
includes taxes & fees
23 Dec - 24 Dec
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is HK$1,868
HK$4,956 total
includes taxes & fees
5 Jan - 6 Jan 2026
Edgewater/Mayo Gateaway w/ Hot Tub
Dining
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"The hotel is obviously and older structure taken over and renovated by Hilton Garden Inn. That said, it is clean, with good amenities, enough space in the rooms. And best of all, the staff is very professional and pleasant. The restaurant staff went out of their way to make me feel welcome just before closing time. Makes a weary traveler's day!"
Urs-Rainer 1-night trip
Posted 3 days ago
Hilton Garden Inn Annapolis Downtown