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

Find Cheap Hostels in Chestertown

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (998 reviews)
"Good hotel"
United States
Michael
$98 nightly
The price is $109
Dec 6 - Dec 7
Total with taxes and fees
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
$64 nightly
The price is $70
Nov 6 - Nov 7
Total with taxes and fees
Driftwood Inn
A living room with a fireplace, a television, and a stone accent wall.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (512 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
$72 nightly
The price is $80
Nov 12 - Nov 13
Total with taxes and fees
Red Roof Inn & Suites Chestertown
A campfire in a stone fire pit by a lakeside at sunset.

4. 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
$124 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
The Lodge at Great Oak Landing
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. 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.
$136 nightly
The price is $150
Nov 9 - Nov 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A garden path leading to a wooden building with a rustic appearance.

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.
$263 nightly
The price is $273
Nov 6 - Nov 7
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

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.
$290 nightly
The price is $321
Nov 8 - Nov 9
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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.
$261 nightly
The price is $277
Nov 11 - Nov 12
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered porch with a wooden bench, potted plants, and a decorative railing.

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.
$440 nightly
The price is $457
Nov 7 - Nov 8
Total with taxes and fees
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
$156 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees
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
$135 nightly
The price is $150
Nov 11 - Nov 12
Total with taxes and fees
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
$110 nightly
The price is $117
Nov 9 - Nov 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A gazebo with a view of a lake at dusk.

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)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
$91 nightly
The price is $101
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A house with a blue front door, two windows, and a small porch.

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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$251 nightly
The price is $278
Nov 6 - Nov 7
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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.
$272 nightly
The price is $301
Nov 6 - Nov 7
Total with taxes and fees
BAYSIDE BUNGALOW
A modern hotel lobby with a long dining table, several chairs, and a bar area.

16. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,011 reviews)
"Very nice stay and staff"
United States
Deborah
$85 nightly
The price is $96
Nov 23 - Nov 24
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

17. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (314 reviews)
"The whole experience was great 👍"
United States
Donald
$101 nightly
The price is $113
Dec 3 - Dec 4
Total with taxes and fees
Hilton Garden Inn Bel Air
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

18. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,000 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
$84 nightly
The price is $93
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

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, (1,004 reviews)
"very clean and staff was very helpful"
United States
Nate
$87 nightly
The price is $97
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

20. 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, (971 reviews)
"The property was in a very nice area. There were a few restaurants near. Very quiet, will definitely stay again."
United States
Rashawna
$107 nightly
The price is $124
Nov 12 - Nov 13
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
Donna 1-night trip
Posted 1 hour ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

Chestertown Hostels information

Number of reviews
4,131
Accommodation
0 Hostels
Lowest Price
$70
Highest Price
$457

Frequently asked questions

What are the best hostels in Chestertown?
You may be able to find reasonable rates at these Chestertown accommodations, which get positive reviews from our customers: Red Roof Inn & Suites Chestertown - Property features at this hotel include free WiFi, free parking, and a 24-hour front desk. The Lodge at Great Oak Landing - Guests can enjoy free WiFi, free parking, and a 24-hour front desk at this hotel.
When is the best time of year to stay in a hostel in Chestertown?
Good weather's definitely a plus when you're discovering new places, so here's some information about the local climate: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to see and do in Chestertown?
Generally, Chestertown is known for its sports, college atmosphere, and festivals. Get out into nature with places like Northern Chesapeake Bay, Chesapeake Bay, and Chestertown Dog Park. Cultural attractions include Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater, and The Mainstay. Locals like to shop at Chestertown Farmers Market.
What's the best way to get to and around Chestertown while staying at a hostel?
Keep this information about transit options in Chestertown on hand to make the most of your stay: You can search for flights to the nearest airport, which is Baltimore, MD (MTN-Martin State), 20.3 mi (32.7 km) from the city center. An alternative is Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.

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