Tolchester Beach Vacation Rentals

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Check prices for these dates

Tonight
Jul 10 - Jul 11
Tomorrow
Jul 11 - Jul 12
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Vacation Rentals in Tolchester Beach

The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (293)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Waterfront Oasis of Annapolis Star
Surround yourself with nature's serenity by the tranquil pool, complete with a soothing waterfall and lush greenery.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is ￥36,194
￥68,102 total
includes taxes & fees
Jul 16 - Jul 17
Waterfront Oasis of Annapolis Star
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and stove, complemented by white cabinetry and a sink.

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

9.8 out of 10, Exceptional, (55)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Secluded Tiny Pool House -Private Pool -Self Check in
Relax by the pool surrounded by lush greenery and enjoy dining or lounging on the deck.

Secluded Tiny Pool House -Private Pool -Self Check in

9.6 out of 10, Exceptional, (7)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
The price is ￥24,130
￥31,343 total
includes taxes & fees
Jul 14 - Jul 15
Secluded Tiny Pool House -Private Pool -Self Check in
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Spanning a tranquil body of water, this iconic bridge offers breathtaking views.

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is ￥14,587
￥43,831 total
includes taxes & fees
Jul 13 - Jul 14
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

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

10.0 out of 10, Exceptional, (90)
"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!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

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
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy cooking in this well-equipped kitchen with oven, microwave, and refrigerator.

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

10.0 out of 10, Exceptional, (5)
"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
Enter a serene space with a sauna and comfortable seating area.

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (41)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is ￥29,248
￥43,869 total
includes taxes & fees
Jul 13 - Jul 14
BAYSIDE BUNGALOW
Cass-N-Reel Luxury Houseboat
Enjoy a serene view of the water from the balcony, featuring a comfortable seating area and dining space.

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
The price is ￥14,478
￥23,229 total
includes taxes & fees
Jul 17 - Jul 18
First Floor Studio Apartment in Historic Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Escape to a serene cabin surrounded by lush greenery and natural beauty.

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

10.0 out of 10, Exceptional, (4)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Relax in this serene outdoor seating area with a glass-top table and wicker chairs, surrounded by a wooden deck and large windows offering views of the surrounding landscape.

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

10.0 out of 10, Exceptional, (187)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Enjoy cooking in this well-equipped kitchen with a range hood, oven, and large sink.

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 ￥22,082
￥73,139 total
includes taxes & fees
Jul 16 - Jul 17
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Enjoy the tranquil atmosphere on our rooftop terrace, overlooking the marina with boats and buildings in the distance.

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 ￥41,305
￥88,571 total
includes taxes & fees
Jul 21 - Jul 22
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Property grounds

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 ! ! !
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Guests can enjoy a scenic pier with a clear view of the surrounding water and natural landscape.

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (30)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
New Tropical Oasis with Rooftop Views, Mins from the Inner Harbor
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel appliances.

New Tropical Oasis with Rooftop Views, Mins from the Inner Harbor

10.0 out of 10, Exceptional, (3)
"We thoroughly enjoyed our stay here. Very clean"
New Tropical Oasis with Rooftop Views, Mins from the Inner Harbor
Waterfront Retreat with Private Dock and Beach
Guests can enjoy serene lakeside views from the dock.

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is ￥32,904
￥55,054 total
includes taxes & fees
Jul 14 - Jul 15
Waterfront Retreat with Private Dock and Beach
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy serene views of the water with seagulls perched on the shore.

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

9.6 out of 10, Exceptional, (40)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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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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.