Photo by Lin R

Talbot County holiday homes

We found 537 holiday rentals — enter your dates for availability
Select from 139 homes, 33 cottages and other holiday rentals in Talbot County to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, including air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular Talbot County destinations on Bookabach

Holiday rentals with weekly discounts – Talbot County

Showing deals for:6 Nov - 13 Nov

Kitchen
Kitchen
Kitchen
Exterior
Exceptional
(27 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
NZ$4,055
for 7 nights, 1 room
NZ$579 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Swimming Pool
Porch Dining Table
Kitchen
Upstairs Hall
Exceptional
(33 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
NZ$23,025
for 7 nights, 1 home
NZ$3,289 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
View from Pier back to house!
Pool
View from Foyer into Great Room
Dining table- seats 10!
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
NZ$13,975
for 7 nights, 1 home
NZ$1,996 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Kitchen with peak into living room
Foyer into Living Room
Living Room into Kitchen/Dining
Foyer with stairs to second floor peak into 1st  floor master bedroom
Exceptional
(90 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
NZ$7,378
for 7 nights, 1 home
NZ$1,054 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Delightful front garden welcomes you when approaching house from driveway
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Convenient open-concept design:  kitchen, dining and living areas
Exceptional
(161 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
NZ$3,792
for 7 nights, 1 home
NZ$542 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Property grounds
Living area
Interior
Room
Exceptional
(14 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
NZ$8,980
for 7 nights, 1 home
NZ$1,283 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Exterior
Exterior
Private kitchen
Interior
Exceptional
(65 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
NZ$13,880
for 7 nights, 1 home
NZ$1,983 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Exterior
New Kitchen 2022
Dining room
Property grounds
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
NZ$6,437
for 7 nights, 1 home
NZ$920 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Sit and stay a while!
View down the lane
Dining Room - Seats 6
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,424
for 7 nights, 1 cottage
NZ$489 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Interior
Private kitchen
Property grounds
Living area
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
NZ$5,224
for 7 nights, 1 home
NZ$746 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Private kitchen
Dining
Interior
Living area
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$5,801
for 7 nights, 1 cottage
NZ$829 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Outdoor dining
Pool
Property grounds
Private kitchen
Exceptional
(214 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
NZ$5,656
for 7 nights, 1 room
NZ$808 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Interior
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Exterior detail
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
NZ$3,538
for 7 nights, 1 cottage
NZ$505 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Beautiful North Bach, MD
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Open-concept living area and kitchen
Exceptional
(17 reviews)

Unbelievable beach views for 6

North Beach

8% off
NZ$3,897
for 7 nights, 1 apartment
NZ$557 per night
includes taxes & fees
Unbelievable beach views for 6
Living area
Exterior
Private kitchen
Property grounds
Exceptional
(19 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island

8% off
NZ$5,097
for 7 nights, 1 cottage
NZ$728 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds
Foyer
Room
Exterior
Exceptional
(26 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
NZ$2,452
for 7 nights, 1 apartment
NZ$350 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Terrace/patio
Living area
Interior
Living area
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

Saint Michaels

17% off
NZ$4,118
for 7 nights, 1 home
NZ$588 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
upstairs offers 2 bedrooms including 1 queen and 4 twin (bunks)
Outdoor dining
Dining
Exterior detail
Exceptional
(30 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt

8% off
NZ$4,086
for 7 nights, 1 cottage
NZ$584 per night
includes taxes & fees
Eastern Shore Waterside Cottage Near St. Michaels
Property grounds
Outdoor dining
Terrace/patio
Exterior detail
Exceptional
(10 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
NZ$5,835
for 7 nights, 1 cottage
NZ$834 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Boutiques and vintage shops are right outside your door
The beautiful marina is just 4 blocks away
Interior
Private kitchen
Exceptional
(10 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
NZ$1,838
for 7 nights, 1 apartment
NZ$263 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Exterior
Interior
Interior
Marina
Exceptional
(52 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
NZ$2,178
for 7 nights, 1 cottage
NZ$311 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Interior
Living area
Private kitchen
Exterior
Exceptional
(49 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
NZ$11,662
for 7 nights, 1 home
NZ$1,666 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Living area
Exterior
Private kitchen
Dining
Exceptional
(27 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
NZ$8,121
for 7 nights, 1 home
NZ$1,160 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Large screened porch with ceiling fan allows outdoor dining and relaxing.
St. Michaels Harbor from Park down street
Front and side view of Blades House from Locust St.
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels

8% off
NZ$5,049
for 7 nights, 1 cottage
NZ$721 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Book a holiday rental for your Talbot County getaway

Learn about the unique charm of Talbot County with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Talbot County

Are you looking for attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Talbot County a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (7.9 mi / 12.7 km)
  • Queenstown Harbor Golf (15.7 mi / 25.2 km)
  • Chesapeake Beach Water Park (25.4 mi / 40.9 km)
  • Talbot Massage (0.7 mi / 1.2 km)
  • Easton Cycle and Sport (0.8 mi / 1.3 km)
  • Hog Neck Golf Course (3.7 mi / 5.9 km)

Exploring the natural landscape of Talbot County

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Talbot County. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Gerry Boyle Park at Great Marsh (13.2 mi / 21.2 km)
  • Long Wharf Park (13.7 mi / 22.1 km)
  • Chesapeake Bay Environmental Center (14.5 mi / 23.4 km)
  • Northern Chesapeake Bay (19.6 mi / 31.5 km)
  • Bay Ridge Beach (23.7 mi / 38.1 km)
  • Sandy Point Beach (23.7 mi / 38.2 km)

Transport 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 centre.

Frequently asked questions

What is the best area to stay in Talbot County when booking a holiday home?
If you're thinking about a trip to Talbot County, Claiborne is one of the most desirable places to stay. Whether you go for a cottage, condo or another property style, you'll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Talbot County?
According to our data, houses are the most popular type of holiday home in Talbot County. But having said that, everyone's idea of an epic trip can vary. Bookabach has holiday homes with every size, shape and budget in mind, so you're sure to discover the best fit for your needs.
How much does it cost to rent a holiday home in Talbot County?
The average price for a holiday home in Talbot County is determined by a number of factors, like property type, length of stay and season. Whether you're searching for a sprawling house with room for friends and family or a cosy cottage that's perfect for two, just enter your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Talbot County?
When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday home. Type in your Talbot County travel dates to view your options on Bookabach. Did someone just say "hot tub"? Use our filters to select the features and amenities you want in your home.
What are popular home amenities in Talbot County?
When it comes to home amenities that people are searching for in Talbot County, off-street parking options, a microwave oven and a fridge are the most popular. With Bookabach holiday homes, you'll have options to fit your style and taste, whether you're planning to get away with your partner, your family or even pets.
Are there large group holiday homes in Talbot County?
Pick from 26 properties in Talbot County that can accommodate 10 or more people. Whether you're organising a holiday with extended family or an event like an anniversary, there's ample room to get your loved ones together under one roof.
What are the top attractions for families in Talbot County?
Keeping the kids entertained during your stay in Talbot County is child's play with these cool family-friendly attractions:
  • Talbot County Visitor Centre
  • Avalon Theatre
  • Chesapeake Bay Maritime Museum
Can I find two-bedroom holiday homes in Talbot County?
Talbot County has 22 two-bedroom holiday homes for you to pick from. Discover a holiday home with all the comfort and space you're looking for at a price that's hard to resist on Bookabach.
Are there holiday homes with WiFi in Talbot County?
Talbot County has 75 holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to scrolling social media, these Bookabach homes make it easy to go online.
How old do you have to be to rent a holiday home in Talbot County?
The minimum age permitted can vary across properties on Bookabach, so be sure to check the rules of the holiday home in Talbot County you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Talbot County for?
The amount of time you can stay in a Talbot County holiday home for is down to each property. Simply tap in your preferred travel dates to see options offering longer term stays. They come with all you require to make your extended trip more enjoyable and comfortable, such as air conditioning and kitchens. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.

More holiday ideas