Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Chestertown holiday homes

Terrace/patio

Holiday Home in Smyrna

Amazing Modern house with a full kitchen and parking
9.2 out of 10, Wonderful, (9 reviews)
"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 €315
includes taxes & fees
18 Jan - 19 Jan
Amazing Modern house with a full kitchen and parking
Interior

Holiday Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is €520
includes taxes & fees
21 Jan - 22 Jan
JVA LUXURY HOUSING
Dining

Holiday Home in Overlea

Spacious 4-bedroom retreat house with plenty of parking
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Property was comfortable. TV streaming isnt a preferred way to watch, "
United States
Joseph M. G.
The price is €489
includes taxes & fees
22 Jan - 23 Jan
Spacious 4-bedroom retreat house with plenty of parking
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"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 €232
includes taxes & fees
18 Jan - 19 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Smart TV

Holiday Home in Berea

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
9.6 out of 10, Exceptional, (5 reviews)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is €294
includes taxes & fees
14 Feb - 15 Feb
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Smart TV, fireplace

Holiday Home in Glen Burnie

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very good, (2 reviews)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is €112
includes taxes & fees
15 Jan - 16 Jan
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Interior

Holiday Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (94 reviews)
"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 €177
includes taxes & fees
18 Jan - 19 Jan
Hidden Fells Point Gem / Private Courtyard Patio
Sun-loungers, beach towels

Holiday Home in Perryville

5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is €529
includes taxes & fees
15 Jan - 16 Jan
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"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 €230
includes taxes & fees
19 Jan - 20 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is €482
includes taxes & fees
15 Jan - 16 Jan
Neptune by the Water - Pet Friendly Fenced Yard
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Holiday Home in Glen Burnie

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (5 reviews)
"This home had everything we needed and more. I say home because it felt like home when we walked in. Super cozy and comfortable. The basement was perfect for our family playing card games. Kitchen had everything we needed. We'll definitely see if this place is avaliable on our next visit. "
United States
Jena F.
The price is €286
includes taxes & fees
24 Jan - 25 Jan
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Smart TV

Holiday Home in Berea

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is €226
includes taxes & fees
5 Feb - 6 Feb
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Exterior detail

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is €264
includes taxes & fees
15 Jan - 16 Jan
BAYSIDE BUNGALOW
Exterior

Holiday Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
The price is €115
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Dining

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12 reviews)
"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 €370
includes taxes & fees
15 Jan - 16 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Dining

Holiday Home in Abingdon

Luxury Waterfront Home Built for Entertaining!
8.8 out of 10, Excellent, (8 reviews)
"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"
United States
Oluwaseyi E.
The price is €734
includes taxes & fees
16 Jan - 17 Jan
Luxury Waterfront Home Built for Entertaining!
Interior

Holiday Home in Middletown

Heated Pool • Private Backyard • Home Theater
2.0 star property
The price is €471
includes taxes & fees
19 Jan - 20 Jan
Heated Pool • Private Backyard • Home Theater
Marina

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is €661
includes taxes & fees
15 Jan - 16 Jan
Fisher House: Steps From USNA + Covered Parking!
Property grounds

Holiday Home in Herald Harbor

Cute, Cozy 2-bedroom house in near Annapolis with water access
2.0 star property
The price is €208
includes taxes & fees
15 Jan - 16 Jan
Cute, Cozy 2-bedroom house in near Annapolis with water access
Terrace/patio

Holiday Home in Kent County

High Tide Haven Suite
The price is €178
includes taxes & fees
15 Jan - 16 Jan
High Tide Haven Suite
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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"This property was amazing. Everything you can ask for in a hotel. The staff is very friendly and always willing to help. The room was very clean. The room and hallway had a very fresh smell. "
Jarrett 2-night trip
Posted 5 days ago
Fairfield Inn & Suites by Marriott Middletown

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
367
Accommodation
485 Holiday Homes
Lowest Price
€112
Highest Price
€734