Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chestertown holiday rentals

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$771
HK$1,236 total
includes taxes & fees
8 Jan - 9 Jan
First Floor Studio Apartment in Historic Chestertown
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$529
HK$974 total
includes taxes & fees
12 Jan - 13 Jan
Guest Suite for up to 2 in a Victorian on the Chester River
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43)
"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 HK$496
HK$1,855 total
includes taxes & fees
4 Jan - 5 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Holiday Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (94)
"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 HK$459
HK$1,574 total
includes taxes & fees
11 Jan - 12 Jan
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32)
"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 HK$589
HK$1,994 total
includes taxes & fees
5 Jan - 6 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Holiday Home in Glen Burnie

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very good, (2)
"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 HK$701
HK$976 total
includes taxes & fees
3 Jan - 4 Jan
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,612
HK$3,222 total
includes taxes & fees
3 Jan - 4 Jan
Waterfront Oasis of Annapolis Star
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Holiday Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
The price is HK$660
HK$1,030 total
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
The price is HK$1,238
HK$3,878 total
includes taxes & fees
4 Jan - 5 Jan
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Fridge, microwave, oven, stovetop
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Apartment in Historic District

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (27)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
United States
betsy b.
The price is HK$1,324
HK$2,450 total
includes taxes & fees
4 Jan - 5 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is HK$1,362
HK$2,424 total
includes taxes & fees
7 Jan - 8 Jan
Waterfront Retreat with Private Dock and Beach
Marina
Cozy 2br home w/ parking in downtown Annapolis

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
The price is HK$895
HK$2,352 total
includes taxes & fees
4 Jan - 5 Jan
Cozy 2br home w/ parking in downtown Annapolis
Outdoor dining
BAYSIDE BUNGALOW

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,557
HK$2,327 total
includes taxes & fees
5 Jan - 6 Jan
BAYSIDE BUNGALOW
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Holiday Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36)
"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 HK$981
HK$2,459 total
includes taxes & fees
4 Jan - 5 Jan
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

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)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is HK$1,402
HK$2,455 total
includes taxes & fees
11 Jan - 12 Jan
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

Holiday Home in Perryville

5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146)
"Our family was in town from all over the US for family wedding. Plenty of room for all of us and had a great time at the large kitchen table sharing meals and playing games."
United States
lynn p.
The price is HK$2,515
HK$4,679 total
includes taxes & fees
6 Jan - 7 Jan
5-bedroom vacation home 5 minutes from historic Charlestown
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Houseboat in Baltimore

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, (12)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is HK$1,840
HK$4,213 total
includes taxes & fees
5 Jan - 6 Jan
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Holiday Home in Glen Burnie

The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.6 out of 10, Excellent, (8)
"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 HK$848
HK$2,715 total
includes taxes & fees
5 Jan - 6 Jan
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Holiday Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is HK$1,827
HK$4,382 total
includes taxes & fees
4 Jan - 5 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Room was very clean...staff was nice..."
Crystal 1-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chestertown?

Expedia has 24 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.