Find Vacation Homes in Talbot County, MD from $307

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Top Cities in Talbot County

Vacation Homes in Talbot County

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Historic District
10.0 out of 10, Exceptional, (238)
"A great experience all around"
United States
Daniel m.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

North Beach
9.8 out of 10, Exceptional, (14)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

Cape Saint Claire
10.0 out of 10, Exceptional, (38)
"Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!"
United States
Melissa K.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
$333 nightly
The price is $353
Dec 8 - Dec 9
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville
10.0 out of 10, Exceptional, (7)
"Gorgeous home. Pet-friendly with a large pet bowl by the back door. The description said "one bathroom" but actually has 2 toilets, 3 vanities with one shower that is separated by pocket doors. We woke early each morning to amazing sunrises over the water with large windows at the back of the home. Plenty of room to walk our 2 little dogs on beautifully maintained property. Large, well-stocked kitchen with both Keurig and Nespresso machines. Beds are clean, comfortable with quality linens. ...
United States
jeanette
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Historic Row Home 1 Block from Gate 1 at USNA!

Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$654 nightly
The price is $746
Nov 20 - Nov 21
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!

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

Historic District
10.0 out of 10, Exceptional, (200)
"Excellent house and great location!"
United States
Brad B.
Charming Historic Annapolis Home With Two Off-street Parking Places!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
9.8 out of 10, Exceptional, (50)
"The house was so beautiful from top to bottom! It was incredibly well stocked on everything that we needed and we had an incredible weekend! The hosts were very responsive when needed and we can't speak higher about how wonderful this property is! We will certainly be back! "
United States
Julie S.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Million Dollar View of the Chesapeake Bay

Deale
9.8 out of 10, Exceptional, (129)
"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

Waterfront Wildlife Retreat on the Patuxent River

Lusby
10.0 out of 10, Exceptional, (172)
"Absolutely loved staying here! Property was exactly as advertised, well stocked and excellent wildlife watching opportunities!"
United States
Megan O.
Waterfront Wildlife Retreat on the Patuxent River

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (31)
"This was a great place to stay with everything you needed. I loved the furniture in the house and it was well decorated, not to mention the neighborhood was quiet and close to all these good restaurants. Parking was a breeze for us since we drove in two cars. We parked in the wrap around driveway. There is a small fenced in back yard so it was perfect to let the dog run around and do his business. The host was great and couldn’t have asked for a better stay. "
United States
Mateusz K.
$269 nightly
The price is $307
Nov 19 - Nov 20
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Walk to Everything House

Saint Michaels
10.0 out of 10, Exceptional, (83)
"Family of four stay for 4 nights. The place is clean with all the amenities. Comfortable beds & kitchen with washer & dryer. Early American decor gave a touch of class. We enjoyed the short walk to all the shops & restaurants in St Michael’s."
United States
Corey K.
Walk to Everything House

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Historic District
9.2 out of 10, Wonderful, (15)
"Clean, affordable, and a great location that allowed us to easily walk downtown and to the naval academy."
United States
Heather E.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Entire Townhouse in Rock Hall

Rock Hall
10.0 out of 10, Exceptional, (33)
"Had a great stay and enjoyed being close to dining and sailing."
United States
Ethan B.
Entire Townhouse in Rock Hall

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
$284 nightly
The price is $324
Nov 13 - Nov 14
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood

Timeless Charm Meets Modern Comfort

Historic District
10.0 out of 10, Exceptional, (4)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
United States
Rayne R.
Timeless Charm Meets Modern Comfort

Waterfront Estate w Private Pier, Game Room & Bar

Centreville
9.8 out of 10, Exceptional, (33)
"We take a family vacation every year and this was so perfect! Great for the kids. "
United States
Juanita M.
Waterfront Estate w Private Pier, Game Room & Bar

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Historic District
9.2 out of 10, Wonderful, (27)
"Didn’t really use the (small) kitchen because we were just steps from everything and all the restaurants. Impossible to beat the location. "
United States
Chris A.
Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Parking at Randall House Across from USNA Gate 1

Historic District
9.8 out of 10, Exceptional, (50)
"This is a great property for groups staying together and visiting the Naval Academy. Everything you need is within walking distance. We had a wonderful stay"
United States
Gretchen B.
Parking at Randall House Across from USNA Gate 1

Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg

Historic District
10.0 out of 10, Exceptional, (34)
"Great location to all Annapolis has to offer. Spacious. Great for family and friends."
United States
Trevor H.
Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg
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

Find out more about Talbot County

Booking Tips to Find the Best Talbot County Vacation Homes


How much does it cost to rent a vacation home in Talbot County?

You can find incredible Talbot County vacation homes for all types of budgets: between $307 and $746 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Talbot County?

If you are looking for a great deal on your vacation home in Talbot County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Talbot County?

There are 824 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Talbot County?

Begin by entering your trip dates to see what type of Talbot County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Talbot County?

Booking Talbot County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Talbot County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Talbot County along with your vacation property, into a Talbot County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Talbot County Vacation Homes information

Number of reviews
1,111
Accommodation
824 Vacation Homes
Lowest Price
$307
Highest Price
$746

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