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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (999 reviews)
"Good hotel"
United States
Michael
The price is CA $139
CA $154 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

2. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is CA $90
CA $100 total
includes taxes & fees
Nov 9 - Nov 10
Driftwood Inn
A multi-story brick building with a covered entrance and a parking lot.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is CA $102
CA $113 total
includes taxes & fees
Nov 15 - Nov 16
Red Roof Inn & Suites Chestertown
A building with a balcony and large windows, surrounded by trees and a fence.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $140
CA $212 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (127 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is CA $153
CA $174 total
includes taxes & fees
Nov 9 - Nov 10
The Lodge at Great Oak Landing
A wooden bridge leading to a house surrounded by lush greenery.

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 CA $259
CA $389 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Cottage in Middle of Chestertown
A two-story building with a ground-floor commercial space and upper residential units.

7. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $318
CA $475 total
includes taxes & fees
Nov 9 - Nov 10
Newly restored apartment in the heart of Chestertown
A house with a blue door, a front porch, and a garden with various plants and flowers.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is CA $280
CA $392 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is CA $430
CA $645 total
includes taxes & fees
Nov 9 - Nov 10
Wren Retweet- Country Estate in Center of C’Town
A boat deck with a white bench and a view of a calm lake and distant trees.

10. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 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 CA $198
CA $220 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A two-story house with a covered porch, a staircase, and a garden area.

11. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay and would go back again."
United States
Linda
Haven Point Inn and Gallery
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

12. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $96
CA $165 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a blue front door, two windows, and a small porch.

13. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $189
CA $396 total
includes taxes & fees
Nov 12 - Nov 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

14. 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, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is CA $134
CA $149 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Annapolis East-Kent Island by IHG
A building with a gabled roof and a circular vent on the roof.

15. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $283
CA $425 total
includes taxes & fees
Nov 9 - Nov 10
BAYSIDE BUNGALOW
A multi-story hotel with outdoor seating areas and a dock extending into the water.

16. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (857 reviews)
"Great place to stay"
United States
Michael
The price is CA $189
CA $210 total
includes taxes & fees
Nov 15 - Nov 16
Hyatt Place Kent Narrows & Marina
A Hampton Inn hotel with a modern brick facade, large windows, and a clear blue sky.

17. 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)
"Very nice stay and staff"
United States
Deborah
The price is CA $120
CA $135 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

18. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (315 reviews)
"The whole experience was great 👍"
United States
Donald
The price is CA $143
CA $160 total
includes taxes & fees
Dec 3 - Dec 4
Hilton Garden Inn Bel Air
A hotel with a modern facade, a covered entrance, and a red car parked outside.

19. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (974 reviews)
"The property was in a very nice area. There were a few restaurants near. Very quiet, will definitely stay again."
United States
Rashawna
The price is CA $151
CA $175 total
includes taxes & fees
Nov 12 - Nov 13
SpringHill Suites Baltimore White Marsh/Middle River
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

20. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,001 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is CA $119
CA $132 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Grasonville near Kent Island
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

WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham

8/10 Good
"It was alright"
Jerry 1-night trip
Posted 2 hours ago
WoodSpring Suites Baltimore White Marsh - Nottingham

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
3,623
Accommodation
4 Cabin Rentals
Lowest Price
CA $100
Highest Price
CA $645

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. Cozy 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 cozy retreats priced from CA $100 to CA $645 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 Cozy 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 cozy 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 CA $100 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 farther 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 vacation 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.

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