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Tolchester Beach Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Tolchester Beach vacation rentals

Exterior detail

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 661
AED 1,062 total
includes taxes & fees
15 Sep - 16 Sep
BAYSIDE BUNGALOW
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AED 364
AED 583 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is AED 826
AED 1,297 total
includes taxes & fees
19 Aug - 20 Aug
Newly restored apartment in the heart of Chestertown
Beach

4. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 433
AED 1,057 total
includes taxes & fees
18 Aug - 19 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

5. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AED 834
AED 1,565 total
includes taxes & fees
24 Aug - 25 Aug
Bayside Cottage steps from Rock Hall Harbor
TV, fireplace

6. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is AED 674
AED 1,037 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Property grounds

7. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AED 1,178
AED 1,838 total
includes taxes & fees
18 Aug - 19 Aug
Wren Retweet- Country Estate in Center of C’Town
1 bedroom, in-room safe, desk, iron/ironing board

8. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is AED 347
AED 655 total
includes taxes & fees
30 Aug - 31 Aug
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Beach nearby

9. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AED 826
AED 1,390 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

10. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
18 Aug - 19 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
1 bedroom, WiFi, bed sheets

11. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 516
AED 640 total
includes taxes & fees
24 Aug - 25 Aug
Turtle Cove Room
1 bedroom, WiFi (free), bed sheets

12. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 711
AED 1,455 total
includes taxes & fees
18 Aug - 19 Aug
Waterfront Oasis of Annapolis Star
House (3 Bedrooms) | Interior

13. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is AED 823
AED 1,783 total
includes taxes & fees
25 Aug - 26 Aug
Idyllic Pasadena Retreat With Garden + Hot Tub!
Property grounds

14. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a great time staying in this houseboat. It was our first time ever trying a houseboat and it did not disappoint us at all. The house was very clean and the host provides fully stocked kitchen cabinets, toiletries, towels, etc...We spent most of our time on the rooftop patio, soaking in the sun, and relaxing by the fire pit playing games. The bed was very comfortable as well. It was a great weekend, at a great house that has the benefit of being in a gated marina which was an...
United States
Justin M.
The price is AED 868
AED 1,944 total
includes taxes & fees
24 Aug - 25 Aug
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Property grounds

15. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is AED 586
AED 724 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
Coffee/tea maker, fridge, microwave, oven

16. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AED 889
AED 2,601 total
includes taxes & fees
18 Aug - 19 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Dining

17. 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, (16 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
The price is AED 918
AED 1,557 total
includes taxes & fees
18 Aug - 19 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Outdoor dining

18. Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (15 reviews)
"What an amazing experience! Communication was A from the owners. The location was perfect. First home staying at a FloHom and certainly won’t be the last. Thank you for making our anniversary memorable!"
United States
Nicole B.
The price is AED 1,365
AED 2,716 total
includes taxes & fees
24 Aug - 25 Aug
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Coffee/tea maker, fridge, microwave, oven

19. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AED 707
AED 1,795 total
includes taxes & fees
18 Aug - 19 Aug
Pool Loft Suite | Bay Access & Beach Passes
Exterior

20. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is AED 325
AED 1,030 total
includes taxes & fees
18 Aug - 19 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Nice rooms and breakfast was amazing"
Jenri 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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 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.