Vacation Homes in Talbot County

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Talbot County holiday homes

Interior

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, (35 reviews)
"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
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is HK$1,094
HK$2,628 total
includes taxes & fees
1 Mar - 2 Mar
Large 2 bedroom house with private parking in a nice neighborhood
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
9.8 out of 10, Exceptional, (16 reviews)
"The house was clean and a great stay. I enjoyed my stay"
United States
royal b.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Exterior

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, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is HK$6,455
HK$11,057 total
includes taxes & fees
2 Mar - 3 Mar
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is HK$1,172
HK$2,817 total
includes taxes & fees
2 Mar - 3 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport
10.0 out of 10, Exceptional, (129 reviews)
"Great property and location. "
United States
Steve N.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Exterior

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.
Historic District
10.0 out of 10, Exceptional, (128 reviews)
"Great location, very clean house, wonderful stay"
United States
Kathryn O.
Charming garden row home, easy 4 block walk to the heart of Annapolis.
3 bedrooms, desk, iron/ironing board, travel cot

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
Historic District
10.0 out of 10, Exceptional, (41 reviews)
"Perfect location and parking was a big bonus!"
United States
Angela H.
Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
Outdoor pool

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, (8 reviews)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Smart TV, books, printers

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.4 out of 10, Exceptional, (25 reviews)
"House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions we had. Everyone enjoyed their stay with many memories made."
United States
robert p.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
TV

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

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels
9.8 out of 10, Exceptional, (48 reviews)
"Conveniently located!"
United States
Jennifer E.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Interior

200 steps to the beach!

200 steps to the beach!
Rock Hall
10.0 out of 10, Exceptional, (93 reviews)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is HK$1,704
HK$3,173 total
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Exterior

Shewell's A-Frame on Mill Creek

Shewell's A-Frame on Mill Creek
Lusby
10.0 out of 10, Exceptional, (10 reviews)
"Very nice with full amenities. Perfect for us and our dog!"
United States
Gaynel
Shewell's A-Frame on Mill Creek
Interior

Waterfront Estate w Private Pier, Game Room & Bar

Waterfront Estate w Private Pier, Game Room & Bar
Centreville
9.6 out of 10, Exceptional, (38 reviews)
"Great location and plenty of fun"
United States
Carl S.
Waterfront Estate w Private Pier, Game Room & Bar
Fridge, microwave, oven, stovetop

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Historic District
10.0 out of 10, Exceptional, (34 reviews)
"Great location and nicely appointed house. "
United States
Jonathan E.
Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater
9.8 out of 10, Exceptional, (26 reviews)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
Edgewater/Mayo Gateaway w/ Hot Tub
Exterior

Peaceful Waterfront Retreat with Private Pool & Pier, Minutes from Annapolis

Peaceful Waterfront Retreat with Private Pool & Pier, Minutes from Annapolis
Cape St. John
10.0 out of 10, Exceptional, (116 reviews)
"Beautiful location! The house was clean and had everything we needed. Would love to come back one day. Would highly recommend!!! "
United States
Will C.
Peaceful Waterfront Retreat with Private Pool & Pier, Minutes from Annapolis
Smart TV, fireplace, books, offices

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Port Republic
10.0 out of 10, Exceptional, (126 reviews)
"The host was superb and very responsive to our needs. The house was very clean and the view from the back was absolutely stunning to the Chesapeake Bay."
United States
Jeanne O.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Outdoor dining

Discover tranquility near Calvert Cliffs

Discover tranquility near Calvert Cliffs
Saint Leonard
9.8 out of 10, Exceptional, (18 reviews)
"Absolute beautiful home & area. House was clean & welcoming! Would definitely recommend & book again in future "
United States
Anonymous traveller
Discover tranquility near Calvert Cliffs
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Just as one would expect with Hyatt hotel Great food, pool was really nice "
Raymon 3-night trip
Posted 2 days ago
Hyatt Regency Chesapeake Bay

Find out more about Talbot County

Talbot County Vacation Homes information

Number of reviews
938
Accommodation
787 Vacation Homes
Lowest Price
HK$2,628
Highest Price
HK$11,057

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