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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
The price is CA $137
CA $152 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

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
The price is CA $101
CA $112 total
includes taxes & fees
Nov 16 - Nov 17
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

3. 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 $151
CA $173 total
includes taxes & fees
Nov 9 - Nov 10
The Lodge at Great Oak Landing
A row of motel rooms with stone walls and red doors.

4. 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
Nov 7 - Nov 8
Driftwood Inn
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.
The price is CA $138
CA $210 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

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 $257
CA $367 total
includes taxes & fees
Nov 7 - Nov 8
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.
The price is CA $314
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
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.
The price is CA $277
CA $381 total
includes taxes & fees
Nov 12 - Nov 13
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.
The price is CA $426
CA $609 total
includes taxes & fees
Nov 8 - Nov 9
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 $196
CA $217 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
The price is CA $244
CA $271 total
includes taxes & fees
Nov 8 - Nov 9
Haven Point Inn and Gallery
Two Adirondack chairs facing a calm body of water with a clear sky above.

12. 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 $127
CA $141 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Annapolis East-Kent Island by IHG
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

13. 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 $95
CA $163 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
A building with a gabled roof and a circular vent on the roof.

14. 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 $279
CA $401 total
includes taxes & fees
Nov 8 - Nov 9
BAYSIDE BUNGALOW
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

15. 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
The price is CA $187
CA $208 total
includes taxes & fees
Nov 16 - Nov 17
Hyatt Place Kent Narrows & Marina
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, (1,000 reviews)
"Very nice stay and staff"
United States
Deborah
The price is CA $119
CA $133 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn & Suites Edgewood/Aberdeen-South
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

17. 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 $181
CA $403 total
includes taxes & fees
Nov 9 - Nov 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

18. 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, (1,005 reviews)
"very clean and staff was very helpful"
United States
Nate
The price is CA $122
CA $137 total
includes taxes & fees
Nov 29 - Nov 30
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

19. 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
The price is CA $141
CA $158 total
includes taxes & fees
Dec 3 - Dec 4
Hilton Garden Inn Bel Air
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, (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
The price is CA $150
CA $173 total
includes taxes & fees
Dec 3 - Dec 4
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.
View all properties

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top reviews in Chestertown

A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
Vandiver Inn

Vandiver Inn

Vandiver Inn
Havre De Grace

10/10 Excellent

Friendly staff, nice fresh breakfast, beautiful and well maintained building. Fully recommended!!
Canada
Aimara Z
Reviewed June 6, 2026
Vandiver Inn

Frequently Asked Questions

What should I expect during my aparthotel stay in Chestertown?

You're likely to stay centrally in Chestertown when you book an aparthotel or serviced apartment. You can also come to Chestertown for its sporting events and university setting.

How many aparthotels will I find in Chestertown?

Even though there aren't many aparthotels bookable on Expedia and located in Chestertown, you'll find plenty of choices with 45 lodging options. We can help you find options that are similar to an aparthotel such as an apartment or condo.

What should I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. While here, Chestertown Historic District and Rolphs Wharf Marina are other places worth a visit.

What is an aparthotel?

An aparthotel is both a hotel and an apartment, providing the amenities you expect from a traditional hotel, and more space and privacy found in an apartment. Feel like a local when you return to your apartment-like space, often located centrally in Chestertown. Enjoy making home-cooked meals in the full kitchen or kitchenette and having extra space to spread out while you're in town.

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