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Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chestertown holiday homes

TV, fireplace

1. 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 AU$401
includes taxes & fees
5 Aug - 6 Aug
Secluded Cottage in Middle of Chestertown
Property grounds

2. 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)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is AU$727
includes taxes & fees
1 Sept - 2 Sept
Wren Retweet- Country Estate in Center of C’Town
Exterior detail

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$402
includes taxes & fees
31 Aug - 1 Sept
BAYSIDE BUNGALOW
Smart TV

4. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AU$546
includes taxes & fees
3 Aug - 4 Aug
Bayside Cottage steps from Rock Hall Harbor
TV

5. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is AU$135
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom house in Aberdeen with WiFi and AC
Interior

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AU$633
includes taxes & fees
31 Aug - 1 Sept
Family Retreat at Lansdowne Manor
Dining

7. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AU$582
includes taxes & fees
17 Aug - 18 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

8. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is AU$480
includes taxes & fees
13 Aug - 14 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
1 bedroom, iron/ironing board, free WiFi, bed sheets

9. Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AU$291
includes taxes & fees
3 Aug - 4 Aug
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Interior

10. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is AU$550
includes taxes & fees
30 Aug - 31 Aug
Abingdon Haven Hideaway
Interior

11. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (98 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AU$325
includes taxes & fees
30 Aug - 31 Aug
Hidden Fells Point Gem / Private Courtyard Patio
Coffee/tea maker, fridge, microwave, oven

12. Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (4 reviews)
"Overall you’re getting what you pay for. The downstairs toilet didn’t work and there weren’t any towels or lotion but the place was spacey and nice"
United States
Tobi A.
The price is AU$386
includes taxes & fees
4 Aug - 5 Aug
Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Exterior

13. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (49 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AU$473
includes taxes & fees
12 Aug - 13 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Coffee/tea maker, fridge, microwave, oven

14. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (17 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AU$336
includes taxes & fees
2 Aug - 3 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Interior

15. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is AU$483
includes taxes & fees
1 Sept - 2 Sept
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV

16. Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
9.0 out of 10, Wonderful, (9 reviews)
"Listing was better than expected. Highly recommend."
United States
Patrick S.
The price is AU$323
includes taxes & fees
1 Sept - 2 Sept
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Outdoor spa tub

17. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (35 reviews)
"10/10 stars! We had a wonderful stay! It was very clean and well organized! Loved it"
United States
Amy L.
The price is AU$691
includes taxes & fees
12 Aug - 13 Aug
Idyllic Pasadena Retreat with Garden + Hot Tub!
Exterior detail

18. Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere
Patterson Place
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home just two blocks from the park. The owner was extremely friendly and responsive! Hoping to stay here again sometime!"
United States
Lisa A.
The price is AU$370
includes taxes & fees
3 Aug - 4 Aug
Patterson Park Gem, Walk Everywhere
Smart TV, printers

19. Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
8.6 out of 10, Excellent, (7 reviews)
"Host was very friendly and the space was large and clean! "
United States
Mia H.
The price is AU$404
includes taxes & fees
14 Aug - 15 Aug
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Smart TV

20. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (14 reviews)
"THE PERFECT WATERSIDE GETAWAY!!! The Hideaway Spot is a true GEM of a location/property for "
United States
Karen M.
The price is AU$763
includes taxes & fees
5 Aug - 6 Aug
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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

10/10 Excellent
"Great location for experiencing Annapolis. Hotel is clean well maintained but gives the feel of an old Inn. Rooms are nice and up to date"
Jeff 6-night trip
Posted 14 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
3,984
Accommodation
458 Holiday Homes
Lowest Price
AU$81
Highest Price
AU$313