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

Riads in Chestertown

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No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

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

2. 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
$72 nightly
The price is $80
Nov 12 - Nov 13
Total with taxes and fees
Red Roof Inn & Suites Chestertown

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
$64 nightly
The price is $70
Nov 7 - Nov 8
Total with taxes and fees
Driftwood Inn

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.
$136 nightly
The price is $150
Nov 9 - Nov 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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
$124 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
The Lodge at Great Oak Landing

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.
$253 nightly
The price is $262
Nov 7 - Nov 8
Total with taxes and fees
Secluded Cottage in Middle of Chestertown

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

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.
$257 nightly
The price is $272
Nov 12 - Nov 13
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

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.
$420 nightly
The price is $436
Nov 8 - Nov 9
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town

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

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
$194 nightly
The price is $215
Nov 8 - Nov 9
Total with taxes and fees
Haven Point Inn and Gallery

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

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.
$260 nightly
The price is $287
Nov 9 - Nov 10
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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
$91 nightly
The price is $101
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

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.
$259 nightly
The price is $287
Nov 7 - Nov 8
Total with taxes and fees
BAYSIDE BUNGALOW

16. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,000 reviews)
"Very nice stay and staff"
United States
Deborah
$85 nightly
The price is $96
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South

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

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

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, (972 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

20. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (855 reviews)
"Great place to stay"
United States
Michael
$134 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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

Find out more about Chestertown

Chestertown Riads information

Number of reviews
3,621
Accommodation
0 Riads
Lowest Price
$70
Highest Price
$436

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