Tolchester Beach Holiday Rentals

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Our top choices for Tolchester Beach holiday rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is NZ$279
includes taxes & fees
6 Apr - 7 Apr
First Floor Studio Apartment in Historic Chestertown

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$470
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

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, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is NZ$565
includes taxes & fees
5 Apr - 6 Apr
Large 2 bedroom house with private parking in a nice neighborhood

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$508
includes taxes & fees
23 Apr - 24 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$728
includes taxes & fees
6 Apr - 7 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 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 NZ$675
includes taxes & fees
5 Apr - 6 Apr
Pool Loft Suite | Bay Access & Beach Passes

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (10 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is NZ$259
includes taxes & fees
8 Apr - 9 Apr
Secluded Tiny Pool House -Private Pool -Self Check in

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

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is NZ$372
includes taxes & fees
5 Apr - 6 Apr
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is NZ$549
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat with Private Dock and Beach

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is NZ$349
includes taxes & fees
17 Apr - 18 Apr
High Tide Haven Suite

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is NZ$630
includes taxes & fees
15 Apr - 16 Apr
Bayside Cottage steps from Rock Hall Harbor

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$745
includes taxes & fees
6 Apr - 7 Apr
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$1,056
includes taxes & fees
15 Apr - 16 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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, (8 reviews)
"Great place!"
United States
Chris A.
The price is NZ$757
includes taxes & fees
15 Apr - 16 Apr
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$798
includes taxes & fees
5 Apr - 6 Apr
Waterfront Oasis of Annapolis Star

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home. Great location. Super clean. Would definitely stay there again."
United States
Sean S.
The price is NZ$997
includes taxes & fees
7 Apr - 8 Apr
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$919
includes taxes & fees
5 Apr - 6 Apr
Charming Pet-Friendly Stay - Near Bay & Beaches.

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$523
includes taxes & fees
30 Apr - 1 May
BAYSIDE BUNGALOW

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 traveller
The price is NZ$1,518
includes taxes & fees
5 Apr - 6 Apr
Serenity on the Cove

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is NZ$726
includes taxes & fees
5 Apr - 6 Apr
Grandma’s Cottage will wrap around you like a warm hug
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

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 favorite 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 depends 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 NZ$279 per night. Entering your travel dates in the search wizard you might find 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.