Top rated rentals — Talbot County
Destination guide

Book a vacation rental for your Talbot County getaway

Experience the unique character of Talbot County with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Things to do

Activities and attractions in and around Talbot County

Are you looking for things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Talbot County a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • St. Michaels Winery (7.9 mi / 12.7 km)
  • Queenstown Harbor Golf Club (15.7 mi / 25.2 km)
  • Chesapeake Beach Water Park (25.4 mi / 40.9 km)
  • Hog Neck Golf Course (3.7 mi / 5.9 km)
  • Queenstown Harbor Golf Links (15.7 mi / 25.2 km)
  • U.S. Naval Academy Golf Club (25.9 mi / 41.6 km)
Natural features

Exploring the natural landscape of Talbot County

Whether you're looking for adventure or just want to spend some time taking in the scenery, Talbot County is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Bay Environmental Center (14.5 mi / 23.4 km)
  • Harriet Tubman Underground Railroad National Historical Park (22.7 mi / 36.5 km)
  • Sandy Point Beach (23.7 mi / 38.2 km)
  • Blackwater National Wildlife Refuge (24.5 mi / 39.4 km)
  • Sandy Point State Park (24.6 mi / 39.6 km)
  • Maryland Quiet Waters Park (25.5 mi / 41 km)
How to get there

Transportation options to and around Talbot County

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 2.6 mi (4.2 km) from the city center.

What are the top vacation rentals in Talbot County?

From extravagant houses to rustic log cabins, Vrbo has properties to suit all sorts of tastes and budgets. Pack your bags and check out these top vacation rentals in Talbot County:

  • "New St. Michaels Estate - Pier": If you're after someplace in Easton with 5 bedrooms and the comforts of home, this escape is calling your name. Amenities include an electric car charging station and a bicycle.
  • "Stay In The Heart Of Saint Michaels": Settle in at this option in St. Michaels and you'll have access to cookware, dishware and utensils, coffee and tea making facilities and more. It has 2 bedrooms to accommodate your favorite people.

For even more great options, use the search bar at the top of the page to find the perfect Talbot County vacation rental for you.

What are the best tiny house vacation rentals in Talbot County?

You need only take a look inside our tiny house vacation rentals in Talbot County to find out that great things really do come in little packages. Ingeniously designed to maximize every spare inch of space, these fun-sized digs deliver a big vacation experience:

  • Leave the everyday behind and disappear to "Annapolis Waterfront "tiny House" In Garden Setting". This getaway in Parole packs plenty of comforts into its cozy space, such as a toaster and an iron and ironing board.
  • "A Serene Tiny Home Experience" comes with plenty of conveniences, such as nearby museums and a nearby river. Located in Parole, you'll be able to live big in this small but well-designed property.

What are the top-rated vacation rentals for weekend getaways in Talbot County?

While long trips overseas are epic, there's something undeniably lovely about slipping off for a weekend getaway. These properties in Talbot County are ideal for just that:

  • "Carpenter St. Cottage In The Heart Of St Michaels Village" - Located in St. Michaels, there's loads of awesome stuff to see and do right on the doorstep of this rental property. Handy amenities like towels and air conditioning make this getaway even sweeter!
  • "Waterfront Property, Kayaks, Private Dock" - With a water park and a TV, not to mention its convenient location in St. Michaels, you won't want to check out of this property.

Can I find studio apartments for rent in Talbot County?

Forget about booking a bland hotel room and opt for one of our studio apartments in Talbot County. Here's where you can hunker down in your own pad and enjoy your next travel destination like a local:

  • Sleep, eat, chill with friends ... Do it all from the compact yet smartly designed single space at "2 - Cambridge Room: 1 Bedroom, 1 Bathroom". Located in Lemvig, internet services and a TV are among the conveniences here.
  • Alternatively, use "5 - Tilghman Island Room - A Circa 1865 Queen Anne Victorian B&B With 6 Uniquely Furnished En Suite Rooms" as your base to discover the area around you. This appealing retreat is in Easton and offers a fireplace and off-street parking options.

Can I find short term rentals in Talbot County?

Book yourself an inexpensive cabin or live it up in a luxury apartment. Vrbo has a great range of short-term rentals for your getaway in Talbot County. Take a look at these properties for some inspiration:

  • "Carpenter St. Cottage In The Heart Of St Michaels Village" in St. Michaels is a perfect place for a short-term stay. It's within easy reach of the town center, so you'll be able to see all the best sights without having to travel too far.
  • Otherwise, bunk down for day or two at "Waterfront Property, Kayaks, Private Dock" and explore the best bits of St. Michaels. This vacation rental also welcomes short-stay guests and is a good choice if you like being close to the action.

What are the best romantic weekend getaways in Talbot County?

If you'd like to surprise your special someone, take them somewhere special! Organize a romantic weekend getaway in Talbot County at one of these hideouts and let love bloom:

  • Bond as a couple at "New St. Michaels Estate - Pier". This Easton vacation rental is custom-made for romance, offering amenities like beauty services and a fireplace to help set the mood.
  • Alternatively, plan an amorous weekend escape at "Stay In The Heart Of Saint Michaels". Located in St. Michaels, it offers beauty services, outdoor furniture and other bonuses.

What are the best large group vacation rentals in Talbot County?

When it comes to planning a vacation, we think the more people the merrier. If you're looking for somewhere with ample space to fit friends or family, one of these large group vacation rentals in Talbot County will be just the ticket:

  • "Country Home And Bunk House - Wifi": With 6 bedrooms, everyone can join the fun at this sought-after getaway in Eagle. A kitchen and a firepit are just a couple of the amenities offered here.
  • "Waterfront Estate. Walk To St. Michaels": Located in St. Michaels, this roomy option has 6 bedrooms and is another favorite for a get-together with loved ones. There's plenty to keep guests content and comfortable, including a firepit and a nearby river.

What are the best houses for rent with a pool in Talbot County?

Get ready to take your pick and jump right in. Here are a couple of exceptional house rentals in Talbot County where life is cooler by the pool:

  • Welcome to "Premier St. Michaels Cottage - T. Blades House", where the first item on your itinerary should be getting acquainted with the pool. This getaway is located in St. Michaels and comes with a host of family-friendly amenities, including a living room and a dining table.
  • Spring out of bed and enjoy an early morning dip at "Large - In Town - Historic House On Harbor In St Michaels" in St. Michaels. A stereo and a barbecue grill are just two of the many amenities at this exceptional option.

What are the best large family vacation rentals in Talbot County?

Perhaps you're organizing a trip to celebrate a special milestone, or reuniting with loved ones you haven't seen for ages. Whatever the reason, you're going to want lots of space. One of these large family vacation rentals in Talbot County could be just the thing:

  • Located in Easton, "New St. Michaels Estate - Pier" has 5 bedrooms and can sleep up to 10 people. A few of the conveniences here include a fenced pool and childrens activities.
  • Another terrific option, "Large - In Town - Historic House On Harbor In St Michaels" in St. Michaels offers 6 bedrooms and accommodates up to 9 people. A microwave oven and a living room will help keep everyone comfortable and happy.

Can I find family cabin rentals in Talbot County?

Toast marshmallows and enjoy a round of cards. These cabins in Talbot County are fantastic bases to spend some family time:

  • "Boulder Ridge Cabin - A Private Chalet In The Woods" - Located in Friendsville, this inviting escape features amenities such as nearby birdwatching activities and a porch.
  • "Fw Drei - Landhaus Ostseeblick" - Amenities like a pool table and coffee and tea making facilities also make this a favorite among families. Head to this Crystal City hideaway and enjoy some time in nature.

For more options, use the search bar at the top of the page and adjust the filters to find the Talbot County vacation rental that's perfect for your needs.