Tolchester Beach, Chestertown holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Tolchester Beach that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as air conditioning and a pool. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Tolchester Beach

Showing deals for:26 Sept - 3 Oct

Exceptional

(5 reviews)

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, MD

17% off

AU$639 per night

includes taxes & fees

Master bedroom.. King-size bed and en-suite bathroom.

Exceptional

(14 reviews)

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Chestertown, MD

12% off

AU$353 per night

includes taxes & fees

Exceptional

(35 reviews)

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall, MD

9% off

AU$2,584 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Tolchester Beach

Showing deals for: 23 Sept - 26 Sept

BAYSIDE BUNGALOW

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

AU$391 per night

includes taxes & fees

Cottage within walking distance to the Bay!

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 cottage

AU$498 per night

includes taxes & fees

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Sleeps 12 · 4 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$1,113 per night

includes taxes & fees

Waterfront Retreat with Private Dock and Beach

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$470 per night

includes taxes & fees

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

AU$805 per night

includes taxes & fees

Peaceful getaway convenient to local amenities including beach, boating & food

Sleeps 4 · 2 bedrooms · 1+ bathroom

for 3 nights, 1 cottage

AU$450 per night

includes taxes & fees

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Choose a holiday rental for your Tolchester Beach getaway

Learn about the unique charm of Tolchester Beach with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Tolchester Beach

Do you want to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Tolchester Beach a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Compass Pointe Golf Courses (15.3 mi / 24.5 km)
Cassinelli Winery and Vineyards (14 mi / 22.6 km)
Rocky Point Golf Course (9.8 mi / 15.7 km)
Hazel Miner Monument (15.2 mi / 24.4 km)

Exploring the natural landscape of Tolchester Beach

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Tolchester Beach is a great place to get out in nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

Ferry Park (5.9 mi / 9.5 km)
Rocky Point Park and Beach (9.3 mi / 14.9 km)
Miami Beach (9.3 mi / 15 km)
Downs Park Dog Beach (12.8 mi / 20.7 km)
Eastern Neck National Wildlife Refuge (13.1 mi / 21.1 km)
Betterton Beach (13.9 mi / 22.4 km)

Transport options to and around Tolchester Beach

The nearest airport is in Baltimore, MD (MTN-Martin State), located 12.4 mi (20 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Baltimore Washington International Airport (BWI), which is 23.3 mi (37.6 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Tolchester Beach?

The most desirable types of holiday homes in Tolchester Beach are houses. Want something different? Stayz has a variety of options to match our guests' unique needs, so you'll see holiday properties in lots of sizes and shapes. The perfect fit is ready and waiting for you --- get yours today.

How much does it cost to rent a holiday home in Tolchester Beach?

The average price for a holiday home in Tolchester Beach is determined by a number of factors, like time of year, length of stay and property type. Whether you'd like a sprawling villa with a pool or an apartment for you and your other half, just enter your dates of travel to view stays that offer great value.

How much does it cost to rent a beach house in Tolchester Beach?

When you travel and the size and style of the property will determine the cost of your beachside holiday home. Click on your Tolchester Beach travel dates to see your options on Stayz. Did someone just say "private pool"? Use our filters to select the features and amenities you want in your beach house.

Are there pet-friendly holiday homes in Tolchester Beach?

Good news! Yes. You'll have a choice of four holiday homes that cater to pets in Tolchester Beach. Lots of our pet-friendly holiday homes have an area outdoors for your four-legged pal to have fun in, dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Stayz.

What are popular home amenities in Tolchester Beach?

When it comes to home amenities that guests look for in Tolchester Beach, a water view, a fireplace and a nearby waterfront are at the top of the list. With Stayz holiday homes, you'll have options to match your style and taste, whether you're going on a holiday with family members, friends or even pets.

Are there holiday homes in Tolchester Beach that welcome kids?

Tolchester Beach has four family-friendly holiday homes to choose from. And tracking down a stay that welcomes kids is a breeze with our "Properties good for families" filter. In addition to having the entire place to yourselves, you'll enjoy access to perks and conveniences like multiple bedrooms, full kitchens and yards.

What are the top attractions for families in Tolchester Beach?

Keep the kids entertained at these fabulous family-friendly attractions in Tolchester Beach:

Historical Society of Kent County Maryland
River Arts Chestertown
Garfield Centre for the Arts at the Prince Theatre

Can I find two-bedroom holiday homes in Tolchester Beach?

Tolchester Beach has two two-bedroom holiday homes to choose from. Go for a holiday home with all the space and privacy you need at a fantastic price on Stayz.

Are there holiday homes with WiFi in Tolchester Beach?

Tolchester Beach has three holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to catching up on social media, these Stayz homes make it a cinch to get online.

How can I find holiday homes with air conditioning in Tolchester Beach?

Tolchester Beach has four holiday homes where you can kick back in air-conditioned comfort. To find a stay on Stayz offering this perk, enter your dates of travel and use the filter tool to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Tolchester Beach?

We recommend you check with the Tolchester Beach holiday property you want on Stayz as the age limit varies. However, normally it's 16, 18 or 21.

How long can I rent a holiday home in Tolchester Beach for?

How long you can rent a holiday home in Tolchester Beach varies according to the property. Simply enter your chosen travel dates to view a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Tolchester Beach.