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Tolchester Beach Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Tolchester Beach vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

2. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$261 nightly
The price is $288
Sep 7 - Sep 8
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A building with a gabled roof and a circular vent on the roof.

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$260 nightly
The price is $287
Sep 9 - Sep 10
Total with taxes and fees
BAYSIDE BUNGALOW
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

4. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
$384 nightly
The price is $407
Sep 30 - Oct 1
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

5. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$271 nightly
The price is $281
Sep 7 - Sep 8
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

6. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
$286 nightly
The price is $316
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
A lighthouse with a white exterior, a balcony, and a metal roof.

7. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$289 nightly
The price is $313
Sep 17 - Sep 18
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

8. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
$370 nightly
The price is $421
Sep 15 - Sep 16
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A spacious living area with a dining table, sofa, and a kitchen in the background.

9. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$319 nightly
The price is $352
Sep 7 - Sep 8
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

10. Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Sep 7 - Sep 8
Total with taxes and fees
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

11. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$181 nightly
The price is $196
Sep 14 - Sep 15
Total with taxes and fees
Beachcomber Suite
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

12. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$270 nightly
The price is $286
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

13. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
10.0 out of 10, Exceptional, (1 review)
"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...
United States
Jennifer R.
$135 nightly
The price is $156
Sep 15 - Sep 16
Total with taxes and fees
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

14. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (7 reviews)
$175 nightly
The price is $186
Sep 9 - Sep 10
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

15. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
$310 nightly
The price is $354
Sep 15 - Sep 16
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.

16. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$478 nightly
The price is $497
Sep 7 - Sep 8
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

17. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
$293 nightly
The price is $333
Sep 7 - Sep 8
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

18. Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveler
$1,028 nightly
The price is $1,187
Sep 13 - Sep 14
Total with taxes and fees
Serenity on the Cove
A spacious hallway with a staircase, a seating area with a sofa and armchairs, and a large window with a stained glass design.

19. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (16 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$210 nightly
The price is $243
Sep 7 - Sep 8
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

20. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (14 reviews)
"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"
United States
Chris H.
$339 nightly
The price is $387
Sep 17 - Sep 18
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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 Tolchester Beach Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"Nice hotel overall. Room was cleans and the staff was helpful"
Lillian 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Find out more about Tolchester Beach

Everything you need to know about Tolchester Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tolchester Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tolchester Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tolchester Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tolchester Beach. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tolchester Beach in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tolchester Beach rentals

At Expedia, we put the best Tolchester Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tolchester Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tolchester Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tolchester Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Tolchester Beach?

Yes, we give you a choice of vacation rentals near top points of interest in Tolchester Beach, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Tolchester Beach has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Tolchester Beach offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Tolchester Beach?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Rock Hall Harbor and Washington College.

What are vacation rentals like in Tolchester Beach?

Vacation rentals are private accommodations you can reserve for a short or long stay in Tolchester Beach. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for small groups.