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Tolchester Beach Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Tolchester Beach holiday rentals

A building with a gabled roof and a circular vent on the roof.

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AU$411
includes taxes & fees
7 Nov - 8 Nov
BAYSIDE BUNGALOW
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$219
includes taxes & fees
9 Nov - 10 Nov
First Floor Studio Apartment in Historic Chestertown
A house with a blue front door, two windows, and a small porch.

3. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$412
includes taxes & fees
9 Nov - 10 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A garden path leading to a wooden building with a rustic appearance.

4. 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.
The price is AU$380
includes taxes & fees
7 Nov - 8 Nov
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is AU$460
includes taxes & fees
8 Nov - 9 Nov
Newly restored apartment in the heart of Chestertown
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

6. 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, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is AU$636
includes taxes & fees
8 Nov - 9 Nov
FLOHOM 14 - Luxury Houseboat with Chesapeake Bay Panoramic Views
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is AU$278
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room
A covered porch with a wooden bench, potted plants, and a decorative railing.

8. 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.
The price is AU$631
includes taxes & fees
8 Nov - 9 Nov
Wren Retweet- Country Estate in Center of C’Town
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AU$395
includes taxes & fees
13 Nov - 14 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is AU$197
includes taxes & fees
7 Dec - 8 Dec
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
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.
The price is AU$290
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite
A deck with a view of a marina, including boats and docks.

12. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is AU$370
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

13. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (18 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is AU$446
includes taxes & fees
9 Nov - 10 Nov
B’more Restful. Comfortable Townhome -Easy access to everywhere
A covered outdoor seating area with a wooden ceiling, two chairs, a table, and a wicker sofa.

14. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AU$496
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

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

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.4 out of 10, Exceptional, (18 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.
The price is AU$506
includes taxes & fees
9 Nov - 10 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A bedroom with a large window, a wooden floor, a bed, a bedside table, and a wardrobe.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is AU$423
includes taxes & fees
9 Nov - 10 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

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, (44 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.
The price is AU$450
includes taxes & fees
9 Nov - 10 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Stylish kitchen with open layout and island seating

18. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AU$688
includes taxes & fees
9 Nov - 10 Nov
Pool Loft Suite | Bay Access & Beach Passes
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

19. 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, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is AU$585
includes taxes & fees
15 Nov - 16 Nov
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A spacious hallway with a staircase, a seating area with a sofa and armchairs, and a large window with a stained glass design.

20. 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, (18 reviews)
"Perfect Maryland trip"
United States
Rosa E.
The price is AU$344
includes taxes & fees
8 Nov - 9 Nov
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

8/10 Good
"Need to upgrade decor"
Ashley 1-night trip
Posted 4 hours ago
Best Western Plus Hotel & Conference Center

Find out more about Tolchester Beach

Everything you need to know about Tolchester Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Tolchester Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Tolchester Beach holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tolchester Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tolchester Beach holiday rentals we have selected for you start as low as AU$197 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Tolchester Beach rentals

At Expedia, we put the best Tolchester Beach holiday 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 holiday.

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 holiday rental in Tolchester Beach?

Yes, there are holiday rentals close to the most popular sights in Tolchester Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tolchester Beach has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Tolchester Beach offers a balcony, a garden and a BBQ 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 that 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 wider area, you’ll find Rock Hall Harbor and Washington College.

What are holiday rentals like in Tolchester Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tolchester Beach. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.