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Holiday Homes in Chestertown

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Featured Holiday Homes in Chestertown

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (31)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AU$437
includes taxes & fees
27 Oct - 28 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
9.6 out of 10, Exceptional, (4)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is AU$322
includes taxes & fees
27 Oct - 28 Oct
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Amazing Modern house with a full kitchen and parking
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$550
includes taxes & fees
30 Oct - 31 Oct
Amazing Modern house with a full kitchen and parking
High Tide Haven Suite
The price is AU$314
includes taxes & fees
26 Oct - 27 Oct
High Tide Haven Suite
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$489
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (88)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is AU$324
includes taxes & fees
3 Nov - 4 Nov
Hidden Fells Point Gem / Private Courtyard Patio
Modern New Suite Close to US Capital and BWI Airport
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
The price is AU$225
includes taxes & fees
27 Oct - 28 Oct
Modern New Suite Close to US Capital and BWI Airport
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AU$691
includes taxes & fees
3 Nov - 4 Nov
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very good, (1)
"The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the...
United States
Zach N.
The price is AU$196
includes taxes & fees
8 Nov - 9 Nov
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$652
includes taxes & fees
24 Oct - 25 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (29)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is AU$508
includes taxes & fees
3 Nov - 4 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
The price is AU$350
includes taxes & fees
30 Oct - 31 Oct
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.4 out of 10, Very good, (7)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is AU$541
includes taxes & fees
3 Nov - 4 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Exclusive Sunken Living Room Soaring Exposed Brick
10.0 out of 10, Exceptional, (6)
"Place was amazing. So many amenities. So close to all the tourist attractions as well. Tons of street parking even at late night. Neighborhood is nice and secure. Would certainly stay again! Communication was excellent. "
United States
Mike J.
The price is AU$590
includes taxes & fees
30 Oct - 31 Oct
Exclusive Sunken Living Room Soaring Exposed Brick
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$465
includes taxes & fees
3 Nov - 4 Nov
BAYSIDE BUNGALOW
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
9.8 out of 10, Exceptional, (64)
"Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips."
United States
Anonymous traveller
The price is AU$448
includes taxes & fees
3 Nov - 4 Nov
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
New! Stylish downtown home w/awesome outdoor area!
9.8 out of 10, Exceptional, (25)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AU$875
includes taxes & fees
7 Nov - 8 Nov
New! Stylish downtown home w/awesome outdoor area!
Romantic Hot Tub Getaway, Walking Distance to Fells Point
10.0 out of 10, Exceptional, (32)
"Awesome place.. take advice on parking when offered "
United States
Steven B.
The price is AU$322
includes taxes & fees
3 Nov - 4 Nov
Romantic Hot Tub Getaway, Walking Distance to Fells Point
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146)
" The location and the house! Great communication from owner!! Thank you!!"
United States
steve j.
The price is AU$936
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
10.0 out of 10, Exceptional, (4)
"The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. "
United States
Alexandra C.
The price is AU$474
includes taxes & fees
3 Nov - 4 Nov
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
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 Holiday Homes information

Number of reviews
488
Accommodation
493 Holiday Homes
Lowest Price
AU$196
Highest Price
AU$936