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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14
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, (990 reviews)
"Property was quiet and clean and close to town."
United States
Roberta
The price is CA $138
CA $154 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Chestertown
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 reviews)
"Easy check-in & out. Convenient parking. Room was clean, though there were stains on loveseat, sheets, comforter (look like they’d been there for awhile; washed & put back on)."
United States
Kate
The price is CA $101
CA $112 total
includes taxes & fees
Oct 27 - Oct 28
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. 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 $89
CA $99 total
includes taxes & fees
Oct 23 - Oct 24
Driftwood Inn
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, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $139
CA $223 total
includes taxes & fees
Oct 22 - Oct 23
First Floor Studio Apartment in Historic Chestertown
A large white tent with a peaked roof, surrounded by a grassy area and potted plants.

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, (122 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is CA $152
CA $174 total
includes taxes & fees
Oct 25 - Oct 26
The Lodge at Great Oak Landing
A rustic wooden barn with a red roof, surrounded by lush greenery and a wooden fence.

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 $258
CA $387 total
includes taxes & fees
Oct 25 - Oct 26
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 $316
CA $497 total
includes taxes & fees
Oct 22 - Oct 23
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 $278
CA $404 total
includes taxes & fees
Oct 27 - Oct 28
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 $428
CA $677 total
includes taxes & fees
Oct 26 - Oct 27
Wren Retweet- Country Estate in Center of C’Town
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.

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 $219 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, (16 reviews)
"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."
United States
Joe
The price is CA $188
CA $209 total
includes taxes & fees
Oct 27 - Oct 28
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 $176 total
includes taxes & fees
Oct 22 - Oct 23
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.

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $174
CA $416 total
includes taxes & fees
Oct 25 - Oct 26
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, (1,001 reviews)
"Good location, easy access to local restaurants. The staff is friendly and helpful. I would recommend staying here"
United States
Terry Kyungho
The price is CA $148
CA $164 total
includes taxes & fees
Nov 15 - Nov 16
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 $281
CA $444 total
includes taxes & fees
Oct 22 - Oct 23
BAYSIDE BUNGALOW
A hotel with a modern facade, a covered entrance, and a red car parked outside.

16. 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, (965 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 $174 total
includes taxes & fees
Oct 29 - Oct 30
SpringHill Suites Baltimore White Marsh/Middle River
A multi-story hotel with outdoor seating areas and a dock extending into the water.

17. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (845 reviews)
"Awesome place"
United States
Joseph
The price is CA $210
CA $233 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Place Kent Narrows & Marina
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

18. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (997 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is CA $117
CA $130 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A row of white single-story houses with dark roofs, a paved driveway, and a grassy lawn.

19. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is CA $445
CA $507 total
includes taxes & fees
Nov 2 - Nov 3
Queenstown Harbor Golf Resort
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.

20. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very good, (1,134 reviews)
"Okay for a one night stay. Location is good!"
Canada
Johanne
The price is CA $111
CA $124 total
includes taxes & fees
Oct 22 - Oct 23
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8/10 Good
"breakfast station needs more fruits"
Andre 3-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
4,974
Accommodation
4 Cabin Rentals
Lowest Price
CA $99
Highest Price
CA $677

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 $99 to CA $677 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 $99 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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