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Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

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. "
The price is AU$474
includes taxes & fees
27 July - 28 July
Amazing Modern house with a full kitchen and parking

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. "
The price is AU$725
includes taxes & fees
13 Aug - 14 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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. "
The price is AU$932
includes taxes & fees
21 July - 22 July
5-bedroom vacation home 5 minutes from historic Charlestown

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

9.6 out of 10, Exceptional, (10)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AU$652
includes taxes & fees
14 July - 15 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is AU$1,276
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

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!"
The price is AU$609
includes taxes & fees
21 July - 22 July
Bayside Cottage steps from Rock Hall Harbor

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."
The price is AU$463
includes taxes & fees
15 July - 16 July
BAYSIDE BUNGALOW

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$587
includes taxes & fees
4 Aug - 5 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is AU$1,384
includes taxes & fees
14 July - 15 July
Luxury Waterfront Home Built for Entertaining!

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."
The price is AU$537
includes taxes & fees
27 July - 28 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

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!"
The price is AU$2,142
includes taxes & fees
14 July - 15 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

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

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,016
includes taxes & fees
14 July - 15 July
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

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. "
The price is AU$423
includes taxes & fees
15 July - 16 July
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

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."
Hobbit House one of a kind home

Small House on Gentleman’s Farm

10.0 out of 10, Exceptional, (11)
"Great little getaway, very clean, and the bedding was so comfy! "
The price is AU$474
includes taxes & fees
17 July - 18 July
Small House on Gentleman’s Farm

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."
The price is AU$743
includes taxes & fees
14 July - 15 July
Neptune by the Water

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

Historic Row Home 1 Block from Gate 1 at USNA!

The price is AU$1,051
includes taxes & fees
16 July - 17 July
Historic Row Home 1 Block from Gate 1 at USNA!

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is AU$1,102
includes taxes & fees
21 July - 22 July
Freshly renovated 3-story home 1 block from 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 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chestertown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 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 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.