Top Vacation Homes in Talbot County in 2026

Talbot County Vacation Homes
Expedia.ae

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Talbot County vacation homes

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

Historic District

10.0 out of 10, Exceptional, (35 reviews)

10/10

Exceptional

(35 reviews)

"Beautiful home in a great central location for walking to most downtown and USNA destinations. "

Hunter S.

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

Large 2 bedroom house with private parking in a nice neighborhood

Arnold

9.4 out of 10, Exceptional, (36 reviews)

9.4/10

Exceptional

(36 reviews)

"This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!"

Emily B.

The price is AED 463

AED 463

AED 1,164 total

includes taxes & fees

11 Feb - 12 Feb

Large 2 bedroom house with private parking in a nice neighborhood

1 bedroom, in-room safe, WiFi, bed sheets

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

North Beach

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"Nice place to stay,very close to the beach "

James L.

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

6 bedrooms, desk, iron/ironing board, free WiFi

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

Historic District

9.4 out of 10, Exceptional, (20 reviews)

9.4/10

Exceptional

(20 reviews)

"Great place, excellent location!"

Joseph C.

The price is AED 2,777

AED 2,777

AED 4,861 total

includes taxes & fees

10 Feb - 11 Feb

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 reviews)

"Very clean, and very comfortable beds."

Edward R.

The price is AED 533

AED 533

AED 1,297 total

includes taxes & fees

16 Feb - 17 Feb

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

Eastport

10.0 out of 10, Exceptional, (129 reviews)

10/10

Exceptional

(129 reviews)

"Great property and location. "

Steve N.

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

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

Historic District

10.0 out of 10, Exceptional, (127 reviews)

10/10

Exceptional

(127 reviews)

"Great location, very clean house, wonderful stay"

Kathryn O.

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

3 bedrooms, desk, iron/ironing board, travel crib

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

Historic District

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"Perfect location and parking was a big bonus!"

Angela H.

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

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

Cambridge

9.8 out of 10, Exceptional, (8 reviews)

9.8/10

Exceptional

(8 reviews)

"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. "

Lea F.

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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

9.4 out of 10, Exceptional, (25 reviews)

9.4/10

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."

robert p.

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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

Downtown St. Michaels

9.8 out of 10, Exceptional, (48 reviews)

9.8/10

Exceptional

(48 reviews)

"Conveniently located!"

Jennifer E.

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

200 steps to the beach!

Rock Hall

10.0 out of 10, Exceptional, (93 reviews)

10/10

Exceptional

(93 reviews)

"Beautiful, comfortable home in a great location. "

Stephanie C.

200 steps to the beach!

4 bedrooms, iron/ironing board, free WiFi, bed sheets

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

Prince Frederick

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "

Olivia M.

The price is AED 735

AED 735

AED 1,374 total

includes taxes & fees

10 Feb - 11 Feb

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

3 bedrooms, iron/ironing board, travel crib, WiFi

Shewell's A-Frame on Mill Creek

Lusby

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Very nice with full amenities. Perfect for us and our dog!"

Gaynel

Shewell's A-Frame on Mill Creek

Waterfront Estate w Private Pier, Game Room & Bar

Centreville

9.6 out of 10, Exceptional, (37 reviews)

9.6/10

Exceptional

(37 reviews)

"Great location and plenty of fun"

Carl S.

Waterfront Estate w Private Pier, Game Room & Bar

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

Historic District

10.0 out of 10, Exceptional, (34 reviews)

10/10

Exceptional

(34 reviews)

"Great location and nicely appointed house. "

Jonathan E.

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

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

Exceptional

(26 reviews)

"Very clean, had everything we needed for our stay!"

Jackie R.

Edgewater/Mayo Gateaway w/ Hot Tub

Scenic Waterfront Getaway with Private Pool and Pier, Minutes from Annapolis

Cape St. John

10.0 out of 10, Exceptional, (116 reviews)

10/10

Exceptional

(116 reviews)

"Beautiful location! The house was clean and had everything we needed. Would love to come back one day. Would highly recommend!!! "

Will C.

Scenic Waterfront Getaway with Private Pool and Pier, Minutes from Annapolis

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

Port Republic

10.0 out of 10, Exceptional, (125 reviews)

10/10

Exceptional

(125 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."

Jeanne O.

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

Discover tranquility near Calvert Cliffs

Saint Leonard

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Absolute beautiful home & area. House was clean & welcoming! Would definitely recommend & book again in future "

Anonymous traveler

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.

View all properties