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Chestertown Holiday Rentals

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Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

Holiday Rentals in Chestertown

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
'At Fells Point' CitySide - 'Tons better than a hotel!'
Marina

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is AU$327
includes taxes & fees
18 Feb - 19 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Miscellaneous

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
The price is AU$464
includes taxes & fees
19 Feb - 20 Feb
Cass-N-Reel Luxury Houseboat
Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Marina

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Beach

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

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is AU$404
includes taxes & fees
19 Feb - 20 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (21)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (16)
"One of if not the best VRBO I have ever stayed in. Incredible property and host"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (24)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.
BALTIMORE ROWHOUSE CLOSE TO WATER KING BED PARKING
Interior

BALTIMORE ROWHOUSE CLOSE TO WATER KING BED PARKING

9.4 out of 10, Exceptional, (28)
"This is a very nice and comfortable row house that sits right in between Fells Point and Canton. Safe, quiet street with nice neighbors and you can walk to everything. Communication and access was seamless. Highly recommend it!"
BALTIMORE ROWHOUSE CLOSE TO WATER KING BED PARKING
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Parking

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (78)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
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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Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (745)
"Staff was courteous and friendly. Room was clean and in good order. Check out was quick and very easy."
The price is AU$175
includes taxes & fees
23 Feb - 24 Feb
Comfort Inn & Suites Chestertown
Sagamore Pendry Baltimore
Lobby

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (997)
"Beautiful hotel in great neighborhood with very well-designed and furnished rooms. Unfortunately, the pool area was locked so we didn't get to take in the water views. I thought $70, after tax and mandatory tip, for a half bottle of poor-quality red wine from the hospitality bar was a bit much, even by hotel standards. "
The price is AU$664
includes taxes & fees
12 Mar - 13 Mar
Sagamore Pendry Baltimore
Quality Inn & Suites Bel Air I-95 Exit 77A
Desk, free WiFi, bed sheets, alarm clocks

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

2.5 star property
7.2 out of 10, Good, (1004)
"Great service "
The price is AU$93
includes taxes & fees
17 Feb - 18 Feb
Quality Inn & Suites Bel Air I-95 Exit 77A
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.

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?

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.: This holiday home rental outside of Chestertown is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

How many holiday rentals are there in Chestertown?

Expedia has 27 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Wilmer Park and Kings Town 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 Roundtop Park 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.