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Chestertown Vacation Rentals

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Jul 6 - Jul 7
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Jul 7 - Jul 8
Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20

Vacation Rentals in Chestertown

Amazing Modern house with a full kitchen and parking
Fridge, microwave, stovetop, cookware/dishes/utensils

Amazing Modern house with a full kitchen and parking

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
$309 nightly
The price is $316
Jul 26 - Jul 27
Total includes taxes and fees
Amazing Modern house with a full kitchen and parking
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
$416 nightly
The price is $441
Jul 15 - Jul 16
Total includes taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
$571 nightly
The price is $605
Jul 15 - Jul 16
Total includes taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

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

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
$400 nightly
The price is $424
Jul 8 - Jul 9
Total includes taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Sunset Bayview: sleeps 6
Beach

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
$788 nightly
The price is $835
Aug 2 - Aug 3
Total includes taxes and fees
Waterfront Sunset Bayview: sleeps 6
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
$377 nightly
The price is $400
Jul 8 - Jul 9
Total includes taxes and fees
Bayside Cottage steps from Rock Hall Harbor
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (41)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
$283 nightly
The price is $300
Jul 8 - Jul 9
Total includes taxes and fees
BAYSIDE BUNGALOW
Room for an Island getaway
1 bedroom, iron/ironing board, travel crib, WiFi

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
$204 nightly
The price is $216
Jul 8 - Jul 9
Total includes taxes and fees
Room for an Island getaway
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Beach

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
$318 nightly
The price is $337
Jul 13 - Jul 14
Total includes taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Luxury Waterfront Home Built for Entertaining!
6 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
$849 nightly
The price is $900
Jul 9 - Jul 10
Total includes taxes and fees
Luxury Waterfront Home Built for Entertaining!
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
$321 nightly
The price is $341
Jul 14 - Jul 15
Total includes taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
$1,314 nightly
The price is $1,393
Jul 14 - Jul 15
Total includes taxes and fees
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun loungers, beach towels

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
$1,229 nightly
The price is $1,303
Jul 14 - Jul 15
Total includes taxes and fees
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Smart TV, fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

10.0 out of 10, Exceptional, (1)
"We were visiting family stationed at Aberdeen. Our stay at the property was a wonderful experience from check-in to check-out. Erik was very attentive to the smallest things--wifi for teens—which is a huge deal to them. If we return to the area the location and place are definitively top of our list. "
$268 nightly
The price is $284
Jul 13 - Jul 14
Total includes taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Hobbit House one of a kind home
Property grounds

Hobbit House one of a kind home

10.0 out of 10, Exceptional, (5)
"Our family had a fantastic weekend here. The house fit our needs and was very relaxing and enjoyable."
$333 nightly
The price is $336
Jul 8 - Jul 9
Total includes taxes and fees
Hobbit House one of a kind home
Small House on Gentleman’s Farm
Fridge, microwave, oven, stovetop

Small House on Gentleman’s Farm

10.0 out of 10, Exceptional, (11)
"Great little getaway, very clean, and the bedding was so comfy! "
$314 nightly
The price is $316
Jul 13 - Jul 14
Total includes taxes and fees
Small House on Gentleman’s Farm
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
$453 nightly
The price is $517
Jul 8 - Jul 9
Total includes taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Neptune by the Water
Fridge, microwave, oven, stovetop

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
$453 nightly
The price is $482
Jul 8 - Jul 9
Total includes taxes and fees
Neptune by the Water
Charming Historic Row House in The Heart of Eastport's Horn Point
Terrace/patio

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
$494 nightly
The price is $563
Jul 21 - Jul 22
Total includes taxes and fees
Charming Historic Row House in The Heart of Eastport's Horn Point
Historic Row Home 1 Block from Gate 1 at USNA!
Fridge, microwave, oven, stovetop

Historic Row Home 1 Block from Gate 1 at USNA!

$647 nightly
The price is $738
Jul 16 - Jul 17
Total includes taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!
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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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 Chestertown Dog Park and Urieville Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Rolphs Wharf Marina and Chestertown Historic District 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.