An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chestertown vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥16,219
￥26,023 total
includes taxes & fees
Aug 3 - Aug 4
First Floor Studio Apartment in Historic Chestertown
TV, fireplace

Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥30,079
￥45,754 total
includes taxes & fees
Jul 29 - Jul 30
Secluded Cottage in Middle of Chestertown
Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is ￥65,113
￥97,081 total
includes taxes & fees
Jul 30 - Jul 31
Wren Retweet- Country Estate in Center of C’Town
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
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥11,140
￥20,491 total
includes taxes & fees
Jul 28 - Jul 29
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is ￥19,299
￥46,983 total
includes taxes & fees
Jul 28 - Jul 29
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥23,002
￥28,544 total
includes taxes & fees
Aug 3 - Aug 4
Turtle Cove Room
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥36,862
￥62,023 total
includes taxes & fees
Jul 28 - Jul 29
Waterfront Retreat with Private Dock and Beach
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is ￥23,886
￥29,682 total
includes taxes & fees
Aug 10 - Aug 11
Beachcomber Suite
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥29,489
￥45,498 total
includes taxes & fees
Aug 4 - Aug 5
BAYSIDE BUNGALOW
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥28,670
￥59,565 total
includes taxes & fees
Jul 28 - Jul 29
Bayside Cottage steps from Rock Hall Harbor
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is ￥11,059
￥15,196 total
includes taxes & fees
Jul 28 - Jul 29
Charming 2-bedroom house in Aberdeen with WiFi and AC
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (208 reviews)
"Appreciated the privacy."
United States
Marie
The price is ￥8,683
￥35,953 total
includes taxes & fees
Jul 28 - Jul 29
Cozy Fells Point Gem / In The Heart of Fells Point
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is ￥23,036
￥54,572 total
includes taxes & fees
Aug 12 - Aug 13
Charming Coastal/Country Home w/3 Acres & Sauna!
House (3 Bedrooms) | Interior

Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is ￥62,583
￥79,343 total
includes taxes & fees
Jul 28 - Jul 29
Waterfront Home on Marley Creek!
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (98 reviews)
"Awesome place, great location"
United States
Mark M.
The price is ￥11,304
￥39,358 total
includes taxes & fees
Aug 12 - Aug 13
Hidden Fells Point Gem / Private Courtyard Patio
Interior

Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is ￥65,532
￥80,555 total
includes taxes & fees
Aug 3 - Aug 4
Family Retreat at Lansdowne Manor
Terrace/patio

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is ￥29,489
￥35,253 total
includes taxes & fees
Aug 3 - Aug 4
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is ￥131,719
￥239,355 total
includes taxes & fees
Aug 9 - Aug 10
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Smart TV

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
9.0 out of 10, Wonderful, (9 reviews)
"Listing was better than expected. Highly recommend."
United States
Patrick S.
The price is ￥13,418
￥30,635 total
includes taxes & fees
Jul 31 - Aug 1
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥40,958
￥68,596 total
includes taxes & fees
Jul 28 - Jul 29
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great location and nice staff!"
Amit 2-night trip
Posted 3 hours ago
Holiday Inn Express Annapolis East-Kent Island 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
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  • 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 Garfield Center for the Arts at the Prince Theater, 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?

Cute, Cozy 2-bedroom house near Annapolis with water access: This vacation home rental outside of Chestertown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Chestertown?

Expedia has 26 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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. 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.