Chestertown Vacation Rentals

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Chestertown vacation 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)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,441
￥24,774 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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 ￥10,606
￥19,509 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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!

Vacation 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 ￥12,682
￥40,993 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Vacation Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (93)
"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 ￥9,202
￥31,345 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation 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 ￥14,373
￥43,118 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming Coastal/Country Home w/3 Acres & Sauna!
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Vacation 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 ￥14,037
￥19,558 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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 ￥32,286
￥64,010 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Waterfront Oasis of Annapolis Star
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Vacation Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
The price is ￥12,651
￥20,049 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious Private 2BR Suite in Abingdon with Separate Entrance
House (3 Bedrooms) | 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 ￥24,799
￥77,674 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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 ￥26,515
￥49,252 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is ￥27,295
￥48,572 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Waterfront Retreat with Private Dock and Beach
Marina
Cozy 2br home w/ parking in downtown Annapolis

Vacation 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 ￥22,928
￥53,876 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy 2br home w/ parking in downtown Annapolis
Outdoor dining
BAYSIDE BUNGALOW

Vacation 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 ￥31,194
￥46,623 total
includes taxes & fees
Jan 5 - Jan 6, 2026
BAYSIDE BUNGALOW
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation 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 ￥19,652
￥49,252 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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

Vacation 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 ￥23,392
￥43,112 total
includes taxes & fees
Jan 3 - Jan 4, 2026
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

Vacation Home in Perryville

5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is ￥50,394
￥93,758 total
includes taxes & fees
Jan 7 - Jan 8, 2026
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 ￥36,848
￥83,904 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Vacation Home in Glen Burnie

The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is ￥16,985
￥54,390 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (6)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ￥36,595
￥87,770 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Two issues: No blackout curtains, and their parking lot was well lit so not ideal. Also we had 3 people and had to keep reminding them of that in order to get enough towels but otherwise it was pretty good. Wonderful shower, nice bathroom, well lit bathroom and bedroom, great breakfast. "
Stacy 7-night trip
Posted 2 days ago
Holiday Inn Express White Marsh by IHG

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 vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation home rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Chestertown?

Expedia has 23 vacation 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 vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.