Chestertown Vacation Rentals

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Jan 2 - Jan 3
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Jan 3 - Jan 4
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

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
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 ￥15,489
￥24,851 total
includes taxes & fees
Jan 12 - Jan 13
First Floor Studio Apartment in Historic Chestertown
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
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 ￥10,639
￥19,569 total
includes taxes & fees
Jan 5 - Jan 6
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!

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, (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 ￥9,987
￥37,335 total
includes taxes & fees
Jan 4 - Jan 5
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
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 ￥9,231
￥31,442 total
includes taxes & fees
Jan 18 - Jan 19
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
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 ￥11,828
￥40,067 total
includes taxes & fees
Jan 4 - Jan 5
Charming Coastal/Country Home w/3 Acres & Sauna!
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Glen Burnie
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 ￥14,081
￥19,619 total
includes taxes & fees
Jan 8 - Jan 9
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥32,385
￥64,742 total
includes taxes & fees
Jan 3 - Jan 4
Waterfront Oasis of Annapolis Star
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
Bel Air South
The price is ￥12,641
￥20,033 total
includes taxes & fees
Jan 4 - Jan 5
Spacious Private 2BR Suite in Abingdon with Separate Entrance
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
Rosedale
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 ￥24,876
￥77,914 total
includes taxes & fees
Jan 4 - Jan 5
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Fridge, microwave, oven, stovetop
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
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 ￥26,597
￥49,226 total
includes taxes & fees
Jan 4 - Jan 5
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥27,379
￥48,722 total
includes taxes & fees
Jan 19 - Jan 20
Waterfront Retreat with Private Dock and Beach
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
The price is ￥18,618
￥48,156 total
includes taxes & fees
Jan 4 - Jan 5
Cozy 2br home w/ parking in downtown Annapolis
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,348
￥46,853 total
includes taxes & fees
Jan 5 - Jan 6
BAYSIDE BUNGALOW
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

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, (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 ￥19,713
￥49,582 total
includes taxes & fees
Jan 6 - Jan 7
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

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
Berea
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 ￥28,213
￥49,423 total
includes taxes & fees
Jan 5 - Jan 6
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

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
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 ￥50,643
￥94,221 total
includes taxes & fees
Jan 5 - Jan 6
5-bedroom vacation home 5 minutes from historic Charlestown
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
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 ￥37,030
￥84,817 total
includes taxes & fees
Jan 5 - Jan 6
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
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 ￥17,069
￥54,658 total
includes taxes & fees
Jan 5 - Jan 6
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ￥36,776
￥88,204 total
includes taxes & fees
Jan 4 - Jan 5
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Breakfast could have been better. Would have been nice to have fresher options. The suite was great, except one remote wasn’t working."
Carolyn 1-night trip
Posted 15 hours ago
Hampton Inn Baltimore/Glen Burnie

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 24 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.