Tolchester Beach Holiday Rentals

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Holiday Rentals in Tolchester Beach

Our top choices for Tolchester Beach holiday rentals

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

10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (38)
"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, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

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

9.8 out of 10, Exceptional, (65)
"Perfect for the wedding I attended and great place to host a short getaway with my brother and his kids."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (305)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

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

10.0 out of 10, Exceptional, (6)
"This property was decorated beautifully. Roomy and functional. We enjoyed coffee on the rear deck. Neighborhood restaurants were great. We had great communication with our host. This trip far exceeded our expectations."
The price is NZ$384
includes taxes & fees
24 Sept - 25 Sept
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (48)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is NZ$501
includes taxes & fees
23 Sept - 24 Sept
BAYSIDE BUNGALOW

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is NZ$561
includes taxes & fees
23 Sept - 24 Sept
Large 2 bedroom house with private parking in a nice neighborhood

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is NZ$251
includes taxes & fees
23 Sept - 24 Sept
First Floor Studio Apartment in Historic Chestertown

John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck

9.4 out of 10, Exceptional, (3)
"We had a wonderful stay at Deanna’s house, everything was clean and easy to get in with self instructions. We liked that the house was also close enough to inner harbor. The owner had great communication too, thank you we’ll plan to stay again soon!! "
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is NZ$1,134
includes taxes & fees
23 Sept - 24 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

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

9.6 out of 10, Exceptional, (44)
"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

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (3)
"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall

Luxury Waterfront Home Built for Entertaining!

5.0 out of 10, (2)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
The price is NZ$1,418
includes taxes & fees
23 Sept - 24 Sept
Luxury Waterfront Home Built for Entertaining!

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (64)
"Had such a great time at this cottage...would definately come back! Close to downtown activities and easy walking to water. Enjoyed our time there!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (13)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is NZ$486
includes taxes & fees
23 Sept - 24 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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

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$251 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?

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.