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

Villas in Chestertown

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A hotel with a beige facade, red brick accents, and a symmetrical design.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (983 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
$107 nightly
The price is $119
Oct 13 - Oct 14
Total with taxes and fees
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, (496 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
United States
Linda
$72 nightly
The price is $80
Sep 29 - Sep 30
Total with taxes and fees
Red Roof Inn & Suites Chestertown
A swimming pool with a wooden deck and lounge chairs, surrounded by trees and a building with a white roof.

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, (112 reviews)
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
United States
Jane
$124 nightly
The price is $137
Sep 23 - Sep 24
Total with taxes and fees
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
$64 nightly
The price is $70
Sep 23 - Sep 24
Total with taxes and fees
Driftwood Inn
A building with a balcony and large windows, surrounded by trees and a fence.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

6. 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.
$293 nightly
The price is $311
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A rustic wooden barn with a red roof, surrounded by lush greenery and a wooden fence.

7. 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.
$264 nightly
The price is $274
Sep 23 - Sep 24
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A garden with a variety of plants and a small bridge.

8. 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.
$463 nightly
The price is $481
Sep 24 - Sep 25
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A two-story house with a covered porch, a staircase, and a garden area.

9. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (14 reviews)
"We had a wonderful stay. Beds were comfortable, and room was quiet. The host, Paul was very helpful and suggested local places to visit and eat. His home cooked breakfast was delightful with fresh herbs from his garden."
United States
Mary
$144 nightly
The price is $159
Oct 22 - Oct 23
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.

10. 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, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
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.

11. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (73 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
$200 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Inn at Huntingfield Creek
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

12. 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.
$259 nightly
The price is $286
Sep 23 - Sep 24
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (1,004 reviews)
"Good hotel for the money and location."
United States
Marc
$114 nightly
The price is $127
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A single-story house with a front porch, a garage, and a small garden area.

14. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$286 nightly
The price is $316
Sep 23 - Sep 24
Total with taxes and fees
BAYSIDE BUNGALOW
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (972 reviews)
"Room was clean. Bathroom small. Staff was pleasant and helpful."
United States
John
$100 nightly
The price is $111
Oct 13 - Oct 14
Total with taxes and fees
Quality Inn Grasonville near Kent Island
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

16. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Close to the bay"
United States
Joshua
$116 nightly
The price is $129
Sep 29 - Sep 30
Total with taxes and fees
Best Western Kent Narrows Inn
A row of white single-story houses with dark roofs, a paved driveway, and a grassy lawn.

17. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
$436 nightly
The price is $482
Sep 24 - Sep 25
Total with taxes and fees
Queenstown Harbor Golf Resort
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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, (1,002 reviews)
"Very big room, everything clean. Great location, friendly staff. Would definitely stay here again."
United States
Vanessa
$91 nightly
The price is $102
Sep 27 - Sep 28
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A Hampton Inn hotel with a modern brick facade, large windows, and a clear blue sky.

19. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,007 reviews)
"We have stayed here several times and this hotel has consistently been a wonderful stay for us!"
United States
walter
$84 nightly
The price is $95
Sep 29 - Sep 30
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel room with two beds, each with patterned bedding, a nightstand with a lamp, and a framed picture on the wall.

20. Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.2 out of 10, Good, (22 reviews)
"Property is not new, but very well maintained. Staff was super helpful and accommodating, room was clean, bathroom was spotless, plenty of parking spaces. Will definitely stay there again."
United States
Elena
$53 nightly
The price is $60
Oct 23 - Oct 24
Total with taxes and fees
Motel Edgewood
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Lovely set of historic inns. The setting was perfect to explore downtown Annapolis (Maryland Inn). We would have preferred a lower floor with more space in lieu of the top floor which was a bit tight for two. Very little natural light in the room. The rooms could have used water (only offered a $12 bottle!) and sufficient coffee cups for two (received only 1)"
Jamie 2-night trip
Posted 3 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Villas information

Number of reviews
7,440
Accommodation
4 Villas
Lowest Price
$60
Highest Price
$223

Frequently asked questions

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How can I find cheap villas in Chestertown?
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What is there to do near my villa in Chestertown?
If you want to discover the sights of Chestertown, make your way to Rolphs Wharf Marina. It's a winner with travelers and locals alike.

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