Tolchester Beach Holiday Rentals

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Holiday Rentals in Tolchester Beach

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

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

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

10.0 out of 10, Exceptional, (22)
"Adam was very communicative and we had no issues with the house. It was very neat and tidy. The sauna and hated bathroom floors are legit. It is in a secluded place which is nice. "
The price is AU$396
includes taxes & fees
27 Feb - 28 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (20)
"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"
Grasonville Home w/ Private Pool on the Water

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

10.0 out of 10, Exceptional, (24)
"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

Beautiful Chesapeake Bay Views -pet friendly

9.6 out of 10, Exceptional, (114)
"The home accomodated"
Beautiful Chesapeake Bay Views -pet friendly

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (28)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is AU$251
includes taxes & fees
4 Mar - 5 Mar
First Floor Studio Apartment in Historic Chestertown

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (32)
"We immensely enjoyed our stay! The home is a peaceful retreat yet close enough to Annapolis and DC to visit! It was super clean! It was a joy to sit outside and watch the wildlife on the water during the day! Will definitely come back!"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is AU$425
includes taxes & fees
11 Mar - 12 Mar
BAYSIDE BUNGALOW

Waterfront CHeerful 2 with Private Pier

10.0 out of 10, Exceptional, (8)
"Quiet location on the water, well laid out. Very clean and very easy to work with. "
Waterfront CHeerful 2 with Private Pier

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

10.0 out of 10, Exceptional, (5)
"This is a terrific property with tons of room and beautifully appointed. We had a great stay. Beautiful sunsets to the west over the water. "
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

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

9.8 out of 10, Exceptional, (29)
"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

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

9.8 out of 10, Exceptional, (9)
"I took my three daughters on a girls weekend trip and wanted to do something different… This houseboat was perfect! Not only did it have every amenity we could need, but the rooftop was spectacular, the home was modern and efficient, and Brian was an amazing host!"
The price is AU$933
includes taxes & fees
10 Mar - 11 Mar
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
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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Other types of properties in Tolchester Beach you may be interested in

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.2 out of 10, Good, (998)
"No problems"
The price is AU$93
includes taxes & fees
27 Feb - 28 Feb
Quality Inn & Suites Bel Air I-95 Exit 77A

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
8.0 out of 10, Very good, (1002)
"Everything was great love it there"
The price is AU$184
includes taxes & fees
2 Mar - 3 Mar
Hilton Garden Inn Baltimore/White Marsh

Best Western Plus Hotel & Conference Center

2.5 star property
7.6 out of 10, Good, (1002)
"Quiet and clean. Needs an upgrade."
The price is AU$198
includes taxes & fees
9 Mar - 10 Mar
Best Western Plus Hotel & Conference Center
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.

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?

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.: This holiday home rental outside of Tolchester Beach is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

How many holiday rentals are there in Tolchester Beach?

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

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 Ferry Park. In the wider area, you’ll find The Mainstay and Rock Hall Harbor.

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.