Tolchester Beach Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Tolchester Beach vacation rentals

Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$346 nightly
The price is $382
Jun 7 - Jun 8
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (112 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Jun 8 - Jun 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Jul 6 - Jul 7
Total with taxes and fees
Turtle Cove Room
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
$166 nightly
The price is $180
Jun 8 - Jun 9
Total with taxes and fees
Beachcomber Suite
Dining

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, (13 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
$395 nightly
The price is $419
Jun 8 - Jun 9
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
Jun 15 - Jun 16
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Beach

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$266 nightly
The price is $294
Jun 8 - Jun 9
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 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.
$367 nightly
The price is $389
Jun 30 - Jul 1
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (55 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jun 9 - Jun 10
Total with taxes and fees
BAYSIDE BUNGALOW
Exterior

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 place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
$259 nightly
The price is $275
Jun 9 - Jun 10
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (10 reviews)
"Very clean, spacious and quiet!!!!! Beautiful home! "
United States
Jennifer M.
$1,142 nightly
The price is $1,211
Jun 7 - Jun 8
Total with taxes and fees
Luxury Waterfront Home Built for Entertaining!
House (3 Bedrooms) | Interior

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
$449 nightly
The price is $476
Jun 25 - Jun 26
Total with taxes and fees
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
Exterior detail

2 Mi to APG: Edgewood Family Home w/ Fenced Yard

2 Mi to APG: Edgewood Family Home w/ Fenced Yard
Edgewood
4.0 out of 10, (1 review)
"The house was okay. Definitely wasnt cleaned thoroughly as there was still food stains in the fridge and peices of food in the butter tray inside the fridge. The stove would not work until i set the time to the correct time so that was a bit of a question mark as to why that was. There was ants all over inside the house which personally was very disgusting. Both me and my son woke up with ants crawling on us in both the master bedroom and back bedroom. So that is something that should be...
United States
Sean G.
$455 nightly
The price is $481
Jun 25 - Jun 26
Total with taxes and fees
2 Mi to APG: Edgewood Family Home w/ Fenced Yard
Fridge, microwave, oven, stovetop

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
$737 nightly
The price is $840
Jul 1 - Jul 2
Total with taxes and fees
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Property grounds

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.0 out of 10, Wonderful, (12 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
$615 nightly
The price is $701
Jun 8 - Jun 9
Total with taxes and fees
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Fridge, microwave, oven, stovetop

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.
$440 nightly
The price is $502
Jun 8 - Jun 9
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Outdoor pool, a heated pool

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
$436 nightly
The price is $497
Jun 7 - Jun 8
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$457 nightly
The price is $521
Jun 10 - Jun 11
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Living area

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
$180 nightly
The price is $207
Jun 7 - Jun 8
Total with taxes and fees
The Sparrows Nest - in downtown Sparrows Point
Interior

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, (40 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
$278 nightly
The price is $317
Jun 7 - Jun 8
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
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

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

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

4/10 Poor
"Pool and gym is out of order and has been for a long time. Ice machine didn’t work on the first floor. AC is weak in the room. Wall paper literally falling down. Cleanliness is minimum. Takes a long time before you get your deposit back."
Jennifer 1-night trip
Posted 1 hour ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Tolchester Beach

Everything you need to know about Tolchester Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tolchester Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tolchester Beach vacation 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 low season months. For more hustle and bustle, you may prefer to visit Tolchester Beach in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tolchester Beach rentals

At Expedia, we put the best Tolchester Beach vacation 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 vacation.

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 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?

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views: This vacation home rental outside of Tolchester Beach is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

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 larger area, you’ll find Waterman’s Museum and The Mainstay.

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.