An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Exterior

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (982 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
The price is £89
includes taxes & fees
14 Oct - 15 Oct
Comfort Inn & Suites Chestertown
Exterior

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (493 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
United States
Linda
The price is £60
includes taxes & fees
27 Sept - 28 Sept
Red Roof Inn & Suites Chestertown
Outdoor banquet area

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, (110 reviews)
"I booked this stay last minute being undecisive and missed other bookings. The best stay in my state short trip ever. The pictures don't do the place justice."
United States
Irma
The price is £92
includes taxes & fees
24 Sept - 25 Sept
The Lodge at Great Oak Landing
Front of property – evening/night

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (182 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is £53
includes taxes & fees
21 Sept - 22 Sept
Driftwood Inn
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5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £122
includes taxes & fees
29 Sept - 30 Sept
First Floor Studio Apartment in Historic Chestertown
Exterior detail

6. 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 £221
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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7. 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 £208
includes taxes & fees
21 Sept - 22 Sept
Secluded Cottage in Middle of Chestertown
Property grounds

8. 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 £346
includes taxes & fees
29 Sept - 30 Sept
Wren Retweet- Country Estate in Center of C’Town
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9. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (14 reviews)
"We had a wonderful stay. Beds were comfortable, and room was quiet. The host, Paul was very helpful and suggested local places to visit and eat. His home cooked breakfast was delightful with fresh herbs from his garden."
United States
Mary
The price is £97
includes taxes & fees
22 Sept - 23 Sept
Haven Point Inn and Gallery
Property grounds

10. 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 £150
includes taxes & fees
21 Sept - 22 Sept
Inn at Huntingfield Creek
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11. 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, (28 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 £96
includes taxes & fees
23 Sept - 24 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

12. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £221
includes taxes & fees
20 Sept - 21 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior

13. 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)
"Good hotel for the money and location."
United States
Marc
The price is £92
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior detail

14. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £231
includes taxes & fees
28 Sept - 29 Sept
BAYSIDE BUNGALOW
Exterior

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (971 reviews)
"Room was clean. Bathroom small. Staff was pleasant and helpful."
United States
John
The price is £83
includes taxes & fees
14 Oct - 15 Oct
Quality Inn Grasonville near Kent Island
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16. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,002 reviews)
"We have stayed here several times and this hotel has consistently been a wonderful stay for us!"
United States
walter
The price is £71
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior

17. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is £379
includes taxes & fees
20 Oct - 21 Oct
Queenstown Harbor Golf Resort
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18. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (834 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 £126
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
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19. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,000 reviews)
"Very big room, everything clean. Great location, friendly staff. Would definitely stay here again."
United States
Vanessa
The price is £75
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"No free breakfast but the one I had to pay for was good"
Darlene 1-night trip
Posted 12 hours ago
Hilton Garden Inn Kent Island Marina

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
4,043
Accommodation
4 Cabin Rentals
Lowest Price
£53
Highest Price
£379

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 £53 to £379 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 £53 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.