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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A hotel with a beige facade, red brick accents, and a symmetrical design.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (963 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
The price is AU$165
includes taxes & fees
28 Sept - 29 Sept
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (481 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
United States
Linda
The price is AU$108
includes taxes & fees
30 Aug - 31 Aug
Red Roof Inn & Suites Chestertown
A large white tent with a peaked roof, surrounded by a grassy area and potted plants.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (104 reviews)
"Everything was wonderful"
United States
Lynda
The price is AU$172
includes taxes & fees
30 Aug - 31 Aug
The Lodge at Great Oak Landing
A row of motel rooms with stone walls and red doors.

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (180 reviews)
"surprisingly, this place was nice, room was semi-clean. Man at counter was nice even though his tone seemed rough but overall he was just a nice man. Bed sheets were still dirty. the bed my daughter slept on had a small blood stain on it. There was little black stuff all over the bed but besides that it was quiet and thats what i needed"
United States
Vanesa
The price is AU$98
includes taxes & fees
30 Aug - 31 Aug
Driftwood Inn
A building with a balcony and large windows, surrounded by trees and a fence.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (123 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AU$224
includes taxes & fees
3 Sept - 4 Sept
First Floor Studio Apartment in Historic Chestertown
A two-story building with a ground-floor commercial space and upper residential units.

6. 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 traveller
The price is AU$482
includes taxes & fees
30 Aug - 31 Aug
Newly restored apartment in the heart of Chestertown

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is AU$397
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

8. 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 AU$388
includes taxes & fees
1 Sept - 2 Sept
Secluded Cottage in Middle of Chestertown
A two-story house with a porch, a chimney, and a flagpole.

9. 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)
The price is AU$691
includes taxes & fees
30 Aug - 31 Aug
Wren Retweet- Country Estate in Center of C’Town
A two-story house with a covered porch, a staircase, and a garden area.

10. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.8 out of 10, Exceptional, (11 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is AU$186
includes taxes & fees
15 Sept - 16 Sept
Haven Point Inn and Gallery
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

11. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (73 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is AU$278
includes taxes & fees
7 Sept - 8 Sept
Inn at Huntingfield Creek
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

12. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,003 reviews)
"Very nice hotel in an area of mixed use properties. Convenient to shopping, dining and entertainment"
United States
Betty
The price is AU$188
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

13. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is AU$177
includes taxes & fees
9 Sept - 10 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

14. 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 AU$396
includes taxes & fees
29 Aug - 30 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (958 reviews)
"Clean room and easy parking"
United States
Faezeh
The price is AU$154
includes taxes & fees
28 Sept - 29 Sept
Quality Inn Grasonville near Kent Island
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.

16. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (408 reviews)
"Complimentary breakfast was a good option"
United States
Mark
The price is AU$152
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A building with a gabled roof and a circular vent on the roof.

17. 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 AU$431
includes taxes & fees
31 Aug - 1 Sept
BAYSIDE BUNGALOW
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

18. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (569 reviews)
"Beautiful and charming. Very nice staff and great breakfast."
United States
Joan
The price is AU$250
includes taxes & fees
3 Sept - 4 Sept
Vandiver Inn
A multi-story hotel with outdoor seating areas and a dock extending into the water.

19. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (823 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
The price is AU$258
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina
A Hampton Inn hotel with a modern brick facade, large windows, and a clear blue sky.

20. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,001 reviews)
"We have stayed here several times and this hotel has consistently been a wonderful stay for us!"
United States
walter
The price is AU$130
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
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 Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Perfect for business and quick family stop travels. Staff is amazing and extremely generous. Clean and well stocked."
Kyle 1-night trip
Posted 16 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
4,062
Accommodation
3 Cabin Rentals
Lowest Price
AU$98
Highest Price
AU$691

Frequently asked questions

What are the best cabins near Chestertown?
Book one of our 33 cabins in Chestertown and you'll be rewarded with picturesque scenery, outdoor adventure and memories you'll never forget. Cosy Cabin Happiness is the place to go for a relaxing getaway. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is also ideal if you'd love some time out in Mother Nature.
Are there cheap cabins in Chestertown?
For a budget-friendly escape in nature, look no further than our cheap cabins in Chestertown. Wake up in the morning to the sweet sound of birds chirping from one of our cosy retreats priced from AU$98 to AU$691 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best family cabins near Chestertown?
If you're seeking a getaway the kids will go wild for, a family cabin rental in or near Chestertown is ideal. Spend time with the gang at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. It offers a meal delivery service and a travel crib as well as ample outdoor adventure. Country Coziness - Lancaster County Private Cabin is another top pick for small groups or families and comes with a deck and a toaster.
What are the best river cabins near Chestertown?
When you think of the word relaxing, a river cabin near Chestertown should be the first thing that comes to mind. Cabin - - Picturesque Wooded Property With Unique Tiny House is the perfect place to discover your Zen. On top of its beautiful surroundings, it features amenities such as on-site watersports and outdoor furniture. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another appealing option. On-site watersports and a firepit are a few of the conveniences that await you here.
What are the best cabins with pools near Chestertown?
If you love the thought of every day being a pool day, escape to Country Coziness - Lancaster County Private Cabin. It's one of our leading cabin rentals with a pool near Chestertown and comes with handy amenities like a swimming pool and a patio. Amazing Getaway: Enjoy Our Cosy Log Cabins On The Chesapeake Bay is another fantastic place to spend your days splashing around. A swimming pool, a patio and good times are all on the menu here.
What are some great Chestertown cabins?
From chic pads with all the fancy perks to cosy retreats that are easy on the hip pocket, Expedia has cabin rentals to suit every taste and budget. Spend a few days enjoying Mother Nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Conveniences here include a firepit and a fireplace. Another excellent option is Pet - Friendly Lakeview Cabin W. It features a deck, a dock and more.
What are the best weekend cabin rentals in Chestertown?
Nothing's as good as a weekend cabin getaway after a tiring week at work. Ditch your cubicle for a few days in nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. A patio and a firepit are among the amenities it offers. Emails will also be the furthest thing from your mind at Country Coziness - Lancaster County Private Cabin. Put your bags down here and make the most of a swimming pool and a patio.
What are the best cabin prices in Chestertown?
With prices starting at just AU$98 a night for a cabin rental in Chestertown, there's no need to wrestle with that hard-to-pitch tent.
Can I find log cabins in Chestertown?
Kick off your day with a hot coffee in your peaceful log cabin and then try some surfing and swimming. Sound perfect to you? Book a stay at 1850 Historic Log Cabin. Another getaway that comes with lots of character and comfort is Log Cabin In Townsend Delaware. Nearby activities like sea kayaking and hiking will add to the good times here.
What are the highest-rated cabins in Chestertown?
There are some cabin stays that are just about perfect. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a prime example. With an impressive rating, it comes with useful amenities such as a patio, a firepit and loads more. Another terrific option is Pet - Friendly Lakeview Cabin W. A patio and a firepit are a few of the conveniences you'll appreciate here.
What are the top things to see and do in Chestertown?
If you're looking to do some sightseeing around Chestertown, don't miss Washington College. Feeling adventurous? Pick up a car rental and find your way to attractions a little further out, including Rolphs Wharf Marina. There's an amazing world to enjoy beyond your comfortable cabin!
Why should I book a cabin in Chestertown?
For a holiday in the great outdoors at an amazing price, there's nothing better than a cabin. Imagine rising to the sound of birds outside and sipping coffee on a private deck surrounded by stunning vistas. Stay in a cabin in Chestertown to get away from the hectic pace of the city. Whether they're by the beach, in the mountains or near a river, cabins offer a rustic and relaxing experience you'll always remember.
What are the top nature cabins in Chestertown?
Stay at Cabin - - Picturesque Wooded Property With Unique Tiny House and you'll be surrounded by breathtaking nature. Amenities such as on-site watersports and a firepit help make this river cabin in Chestertown a popular choice. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another place where you can escape the concrete jungle and unwind by the river. Conveniences here include on-site watersports and a patio.