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Chestertown Vacation Rentals

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Nov 12 - Nov 13
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Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
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Nov 21 - Nov 23

Vacation Rentals in Chestertown

Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown

Chestertown
9.8 out of 10, Exceptional, (27)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is ￥50,870
￥73,883 total
includes taxes & fees
Nov 14 - Nov 15
Newly restored apartment in the heart of Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
The price is ￥15,252
￥24,471 total
includes taxes & fees
Nov 17 - Nov 18
First Floor Studio Apartment in Historic Chestertown
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
The price is ￥24,264
￥61,557 total
includes taxes & fees
Nov 18 - Nov 19
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Outdoor dining
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Canton
10.0 out of 10, Exceptional, (11)
"My partner and I loved our stay on this houseboat. It’s incredibly clean and has all you need, including the views and vibes. The host, Brian, was so responsive and accommodating too. Would definitely recommend staying here!"
United States
Yeeli M.
The price is ￥40,441
￥92,233 total
includes taxes & fees
Nov 13 - Nov 14
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Marina
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
The price is ￥28,325
￥70,425 total
includes taxes & fees
Nov 16 - Nov 17
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Front of property
Hudson house

Hudson house

3.5 star property
Canton
The price is ￥23,168
￥50,332 total
includes taxes & fees
Nov 13 - Nov 14
Hudson house
Terrace/patio
Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront

Historic District
The price is ￥55,153
￥122,061 total
includes taxes & fees
Nov 13 - Nov 14
Historic Downtown Luxury • USNA • Waterfront
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
The price is ￥15,021
￥43,356 total
includes taxes & fees
Dec 2 - Dec 3
Small House on Gentleman’s Farm
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

2.0 star property
Berea
9.6 out of 10, Exceptional, (4)
"Crystal was a wonderful host with great communication! The check in process was simple and the house was tidy; would definitely recommend. "
United States
Mekiyah H.
The price is ￥15,122
￥31,710 total
includes taxes & fees
Nov 17 - Nov 18
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
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
9.6 out of 10, Exceptional, (19)
"It was very clean and cozy! My partner and I loved staying here! "
United States
Tyaunna W.
The price is ￥10,476
￥19,270 total
includes taxes & fees
Nov 13 - Nov 14
Guest Suite for up to 2 in a Victorian on the Chester River
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
The price is ￥27,115
￥70,910 total
includes taxes & fees
Nov 23 - Nov 24
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is ￥34,664
￥64,505 total
includes taxes & fees
Nov 13 - Nov 14
Grandma’s Cottage will wrap around you like a warm hug
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is ￥34,664
￥41,970 total
includes taxes & fees
Nov 13 - Nov 14
Chesapeake Bay Harbor View in a central location to events/restaurants
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is ￥12,132
￥40,459 total
includes taxes & fees
Nov 16 - Nov 17
Relax on Kent Island in 3 Bedroom Home w/Waterview
Outdoor pool, a heated pool
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 ￥35,434
￥68,320 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Oasis of Annapolis Star
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, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is ￥18,159
￥43,880 total
includes taxes & fees
Nov 13 - Nov 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"Loved sitting on the dock, peaceful, quiet; house has everything you need"
United States
jackie r.
The price is ￥26,961
￥47,978 total
includes taxes & fees
Nov 13 - Nov 14
Waterfront Retreat with Private Dock and Beach
Exterior
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, (12)
"I was impressed with how spacious and clean the house was."
United States
Susan M.
The price is ￥38,515
￥64,505 total
includes taxes & fees
Nov 24 - Nov 25
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

Centreville
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is ￥30,365
￥68,604 total
includes taxes & fees
Nov 17 - Nov 18
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Marina
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
9.6 out of 10, Exceptional, (31)
"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 ￥10,515
￥38,255 total
includes taxes & fees
Nov 13 - Nov 14
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Nice room"
Steve 1-night trip
Posted 16 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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 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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This vacation home rental outside of Chestertown is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

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 Chesapeake Bay and Chestertown Dog 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.