Vacation Homes in Talbot County

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Talbot County vacation homes

Smart TV

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (61 reviews)
"Cozy little home with an ideal location in town to easily access all St. Michael’s restaurants and shops."
United States
Julie S.
Dollhouse in Central Historic St Michaels
Exterior

PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history
Historic District
10.0 out of 10, Exceptional, (222 reviews)
"We had a great time here. It is so close to downtown and USNA. The comfort and convenience is terrific. "
United States
Amy B.
PERFECT LOCATION in the heart of history
Fridge, microwave, oven, stovetop

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (20 reviews)
"Super nice and very clean, perfect for our stay."
United States
Douglas S.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Interior

Charming Historic Annapolis Home With Two Off-street Parking Places!

Charming Historic Annapolis Home With Two Off-street Parking Places!
Historic District
10.0 out of 10, Exceptional, (206 reviews)
"Wonderful weekend in a great location! House was perfect for 3 couples looking to get away for the weekend"
United States
Barb K.
Charming Historic Annapolis Home With Two Off-street Parking Places!
Beach nearby, sun loungers, beach towels

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes
North Beach
10.0 out of 10, Exceptional, (84 reviews)
"Host was wonderful. Place was amazing. We could walk to a lot of restaurants, a brewery, breakfast spot and of course the pier! We will stay here again. "
United States
John B.
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Amazing bayfront views! Lots of great restaurants and boutique shopping nearby. "
United States
Karen G.
"La Licorne" Waterfront Beach Cottage
Smart TV

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Everything was great."
United States
Brandon H.
4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
Beach

Private Cottage on gated estate

Private Cottage on gated estate
Annapolis
10.0 out of 10, Exceptional, (32 reviews)
"Very good location. Our family enjoyed our stay. "
United States
Teresa R.
Private Cottage on gated estate
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
The price is AED 1,102
AED 2,324 total
includes taxes & fees
26 May - 27 May
Charming Annapolis WaterVIEW Home
Exterior detail

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

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Murray Hill
10.0 out of 10, Exceptional, (42 reviews)
"Excellent location, charming thematic decor, perfect small house for a couple."
United States
Lisa F.
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Property grounds

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge
9.8 out of 10, Exceptional, (134 reviews)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Property grounds

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Tilghman Island
10.0 out of 10, Exceptional, (39 reviews)
"We love this property and most definitely plan to stay there again in the future."
United States
Joe F.
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Exterior

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Oxford
10.0 out of 10, Exceptional, (21 reviews)
"Wonderful location for a family reunion. Very close to Oxford but felt nicely secluded. House itself was beautiful and charming, and pool was amazing in this hot weather. Would highly recommend"
United States
Evan C.
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Smart TV, fireplace

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Great home base to explore nearby beaches."
United States
Lisa K.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Terrace/patio

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Admiral Heights
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,114 total
includes taxes & fees
13 May - 14 May
BAYSIDE BUNGALOW
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is AED 256
AED 1,135 total
includes taxes & fees
14 May - 15 May
Walk to Beach! King Bed & Free Beach Passes
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (78 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,574 total
includes taxes & fees
25 May - 26 May
Cozy 2br home w/ parking in downtown Annapolis
Exterior

"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!
Woolford
10.0 out of 10, Exceptional, (8 reviews)
"Great location "
United States
Christopher T.
"Endless Summer" Waterfront on the Chesapeake Bay!
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AED 845
AED 1,024 total
includes taxes & fees
3 Jun - 4 Jun
Waterfront Getaway with Dock
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

Inn at Perry Cabin

Inn at Perry Cabin

8/10 Good
"Beautiful historic building with a breathtaking view. Rooms were nice and comfortable. Food was excellent"
Keith 2-night trip
Posted 1 hour ago
Inn at Perry Cabin