Tolchester Beach Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Tolchester Beach

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (299)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is CA $339
CA $638 total
includes taxes & fees
Jul 30 - Jul 31
Waterfront Oasis of Annapolis Star

Secluded Tiny Pool House -Private Pool -Self Check in

9.6 out of 10, Exceptional, (8)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
Secluded Tiny Pool House -Private Pool -Self Check in

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (59)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $151
CA $429 total
includes taxes & fees
Aug 3 - Aug 4
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (30)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."
The price is CA $234
CA $520 total
includes taxes & fees
Jul 29 - Jul 30
Large 2 bedroom house with private parking in a nice neighborhood

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (88)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (92)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

9.8 out of 10, Exceptional, (10)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
The price is CA $495
CA $1,013 total
includes taxes & fees
Aug 11 - Aug 12
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (32)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (124)
"Nice big home with lots of room to be together"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

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

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $274
CA $411 total
includes taxes & fees
Jul 29 - Jul 30
BAYSIDE BUNGALOW

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

9.6 out of 10, Exceptional, (4)
"Nice house in a quiet, safe, residential neighborhood. Clean and comfortable. Easy access to all the attractions in Baltimore. "
The price is CA $207
CA $685 total
includes taxes & fees
Jul 29 - Jul 30
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (188)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is CA $136
CA $218 total
includes taxes & fees
Aug 4 - Aug 5
First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (102)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Tolchester Beach Hotel Reviews

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?

Secluded Tiny Pool House -Private Pool -Self Check in: This vacation home rental outside of Tolchester Beach offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Tolchester Beach?

Choose from 3 Expedia vacation rentals in Tolchester Beach for a memorable vacation.

What can I see and do in Tolchester Beach?

While exploring the area, visit family-friendly sights like Hazel Miner Monument, or get outside and enjoy nature at Rocky Point Park and Beach. In the larger area, you’ll find The Mainstay and Rock Hall Harbor.

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.