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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov
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, (943 reviews)
"Clean and affordable amenities and a decent breakfast!"
United States
Deanna
The price is £89
includes taxes & fees
25 Aug - 26 Aug
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, (471 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is £52
includes taxes & fees
17 Aug - 18 Aug
Red Roof Inn & Suites Chestertown
Outdoor banquet area

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very good, (94 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is £92
includes taxes & fees
5 Aug - 6 Aug
The Lodge at Great Oak Landing
Exterior

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is £121
includes taxes & fees
5 Aug - 6 Aug
First Floor Studio Apartment in Historic Chestertown
Front of property – evening/night

5. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (178 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is £52
includes taxes & fees
5 Aug - 6 Aug
Driftwood Inn
Exterior

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is £265
includes taxes & fees
5 Aug - 6 Aug
Newly restored apartment in the heart of Chestertown
Exterior

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 £209
includes taxes & fees
2 Sept - 3 Sept
Secluded Cottage in Middle of Chestertown
Exterior

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 £374
includes taxes & fees
6 Aug - 7 Aug
Wren Retweet- Country Estate in Center of C’Town
Exterior

9. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (10 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is £99
includes taxes & fees
5 Aug - 6 Aug
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, (69 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is £149
includes taxes & fees
5 Aug - 6 Aug
Inn at Huntingfield Creek
Exterior

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, (23 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
10 Aug - 11 Aug
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, (27 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £215
includes taxes & fees
5 Aug - 6 Aug
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, (1,000 reviews)
"Very clean hotel,beautiful view and great staff."
United States
Jackie
The price is £98
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

14. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (947 reviews)
"Great staff and breakfast crew. Extremely reasonable price, for convenient location."
United States
Jonathan
The price is £84
includes taxes & fees
24 Aug - 25 Aug
Quality Inn Grasonville near Kent Island
Exterior

15. 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 £283
includes taxes & fees
2 Sept - 3 Sept
Waterfront Retreat with Private Dock and Beach
Exterior detail

16. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £211
includes taxes & fees
17 Aug - 18 Aug
BAYSIDE BUNGALOW
Exterior

17. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"good for a short stay"
United States
chanel
The price is £99
includes taxes & fees
6 Aug - 7 Aug
Best Western Kent Narrows Inn
Exterior

18. 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, (398 reviews)
"Complimentary breakfast was a good option"
United States
Mark
The price is £82
includes taxes & fees
16 Aug - 17 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Reception

19. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (172 reviews)
"Wonderful room, bar and food!"
United States
Leigh
The price is £174
includes taxes & fees
10 Aug - 11 Aug
Kent Island Resort
Exterior

20. 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)
"It was very clean and the staff was friendly as well as professional."
United States
LAURENCE
The price is £74
includes taxes & fees
1 Sept - 2 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"I work in Annapolis and stay at the Calvert House on occasion. It is my go to. The property is clean, the staff is helpful. The in room amenities are very good. It is a quiet hotel, so your sleep should be restful. The lobby and hallway have interesting history exhibits from the building's previous life during colonial times. If you are looking for a clean, affordable and quiet hotel, the Calvert House is a wonderful choice for your stay in Annapolis."
Kathryn 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
3,386
Accommodation
3 Cabin Rentals
Lowest Price
£52
Highest Price
£374

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 £52 to £374 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 £52 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.