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Find Hotels with Balconies in Chestertown, MD from CA $182

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Check availability on Chestertown Hotels with Balconies

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chestertown Hotels with Balconies

The Lodge at Great Oak Landing
Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (58)
"Great place to get some quiet rest by the water"
The price is CA $182
CA $202 total
includes taxes & fees
Aug 7 - Aug 8
The Lodge at Great Oak Landing
5-bedroom vacation home 5 minutes from historic Charlestown
Enjoy a serene lakeside retreat with a grassy area, sandy beach, and dock for boating and fishing.

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is CA $462
CA $858 total
includes taxes & fees
Aug 11 - Aug 12
5-bedroom vacation home 5 minutes from historic Charlestown
Vandiver Inn
Relax on the covered porch with wicker chairs and enjoy the view of the surrounding neighborhood.

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Staff was very friendly. We had a very relaxing stay. "
The price is CA $184
CA $207 total
includes taxes & fees
Aug 18 - Aug 19
Vandiver Inn
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (603)
"Great place to stay. "
The price is CA $218
CA $242 total
includes taxes & fees
Aug 26 - Aug 27
Hyatt Place Kent Narrows & Marina
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
The price is CA $288
CA $348 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour
Kent Island Resort
Surrounded by lush greenery and a serene lake, this historic property offers a picturesque setting with a spacious parking area and a circular driveway.

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is CA $211
CA $284 total
includes taxes & fees
Sep 3 - Sep 4
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (405)
"Staff was very polite and friendly. "
The price is CA $282
CA $348 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Experience the charm of this historic home, where a central island and ceiling fan create a welcoming space.

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is CA $1,171
CA $1,894 total
includes taxes & fees
Aug 7 - Aug 8
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Ospreys perch on a scenic waterfront structure overlooking a serene body of water.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is CA $1,102
CA $1,810 total
includes taxes & fees
Aug 11 - Aug 12
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Watch Deer from a Farm Cottage
Relax in this serene bedroom with a plush bed, ceiling fan, and comfortable wicker chair.

Watch Deer from a Farm Cottage

10.0 out of 10, Exceptional, (2)
"Tracy's place was perfect for that quick, relaxing getaway for our family. The house had everything we needed and when we wanted to get outside, there was plenty of space to play and it was awesome to see all of the animals. Tracy was also very attentive and a wonderful host!"
The price is CA $220
CA $493 total
includes taxes & fees
Aug 8 - Aug 9
Watch Deer from a Farm Cottage
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.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Hotel was very quaint, valet is a little steep at 50 dollars a day so I would recommend off street parking. "
Danielle 2-night trip
Posted 2 days ago
Historic Inns of Annapolis

Frequently asked questions

What can I expect from my stay in Chestertown?
Would you like a relaxing vacation in Chestertown with some nice views? Book one of our hotels with balconies and take in the scenery from your room. Chestertown is known for its sporting events. Think about making time to explore the university setting as well.
What are some of the top hotels with balconies that I might want to consider for my trip to Chestertown?
Great Oak Manor is a top B&B featuring premium bedding and free WiFi in guestrooms. The Lodge at Great Oak Landing is another popular hotel where you can enjoy a room with a balcony.
How many hotels with balconies are there in Chestertown?
Expedia has 2 accommodations with balconies to choose from in Chestertown.
What should I see and do while I'm in Chestertown?
After you've taken in the view from your balcony, put on your walking shoes and hit the streets to explore Chestertown. Get started by checking out Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Garfield Center for the Arts at the Prince Theater. A few other sites and attractions to discover include Chestertown Historic District, Sumner Hall, and Urieville Park.
Is it worth paying more for a room with a balcony in Chestertown?
There are lots of reasons why booking a room that features a balcony may be a good idea. Enjoy views of Chestertown and sunbathe outside without leaving your room. If you're vacationing with your kids, relax in a patio chair on the balcony while they are watching TV inside. If you're vacationing with your spouse, you might want a room with a patio so you can spend some quiet time outside enjoying the local scenery.