Chestertown Holiday Rentals from €197: Search Short-Term Rentals

Check Chestertown holiday rental availability

Holiday Rentals in Chestertown

"Great!"

"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"

"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "

"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "

"Perfect location"

includes taxes & fees

3 Dec - 4 Dec

"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"

On the beach, sun-loungers, beach towels

"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."

"This cottage was very cute inside, but could use some curb appeal. When we pulled up, we were worried what the inside looked like. The front bedroom is literally in front of the door, so no one wanted to sleep in that room. The back bedroom in the sunroom, got very cold. The front door would not properly lock, and we realized that you could punch in any number to unlock it. The inside was very cute and updated, but there needs to be some repairs to justify the price. Bedroom doors did not shut...

"The place was just as expected, the neighborhood is cute and quiet, the pub next door is great, and the water is a short walk away. Will likely stay here again. "

includes taxes & fees

4 Dec - 5 Dec

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"

"Perfect for a romantic weekend away!"

"Excellent experience."

includes taxes & fees

1 Dec - 2 Dec

"We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!"

"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"

includes taxes & fees

30 Dec - 31 Dec

"We really enjoyed this property. It was clean and tidy. Checking in was simple. Parking was straightforward once we noticed the markers giving us clear instructions. The kitchen has everything you need. I stayed in the downstairs bedroom, and the bed and pillows were very comfortable. The downstairs shower is small, but the water pressure is good. Everyone who stayed upstairs enjoyed the amenities. Definitely will try to rent this again for the next time we visit Annapolis."

"All as advertised Wonderful option to a hotel"

"My husband and son really loved their stay at Pat & Ken's VRBO house! They enjoyed going on walks around the neighborhood, visiting the local restaurants, and sitting in the hot tub. It was perfect for our family. Pat & Ken are such gracious hosts, and we will definitely stay here again!"

"I took my three daughters on a girls weekend trip and wanted to do something different… This houseboat was perfect! Not only did it have every amenity we could need, but the rooftop was spectacular, the home was modern and efficient, and Brian was an amazing host!"

includes taxes & fees

2 Dec - 3 Dec

"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "

includes taxes & fees

10 Dec - 11 Dec

"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"

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Other types of properties in Chestertown you may be interested in

"Very polite service. The room was clean and comfortable. "

includes taxes & fees

22 Dec - 23 Dec

"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."

includes taxes & fees

5 Dec - 6 Dec

"Great!"

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €197 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Chestertown properties

5/5 Excellent

"Very polite service. The room was clean and comfortable. "

A verified traveller stayed at Comfort Inn & Suites Chestertown

Posted 2 days ago

Holiday Inn Express White Marsh, An IHG Hotel

5/5 Excellent

"The desk staff was terrific- very friendly and helpful. The room was clean, bed extremely comfortable, the breakfast buffet was outstanding, and the pool was great. My only negative comment would be the window treatment in our room- there was no blackout curtain or shade, just one flimsy shade that let far too much light in the room beginning at sunrise. I would have preferred a much darker environment so i could have slept later, instead of being woken up at dawn."

A verified traveller stayed at Holiday Inn Express White Marsh, An IHG Hotel

Posted 5 days ago

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Chestertown?

Expedia has 30 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Rolphs Wharf Marina and Crumpton Auction 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.

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Holiday Rentals in Chestertown

Check Chestertown holiday rental availability

Holiday Rentals in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

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

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

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

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

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

'At Fells Point' Courtyard - Your historically restored apartment

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Amazing views, short walks to great dining!

Relax on Kent Island in 3 Bedroom Home w/Waterview

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Waterfront Oasis of Annapolis Star

USNA Quintessential Charm ~ Downtown Annapolis.

Cass-Away Luxury Houseboat

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Freshly renovated 3-story home 1 block from USNA!

The Heron's Nest at Atlantic Marina

Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Find out more about Chestertown

Recent reviews of Chestertown properties

Comfort Inn & Suites Chestertown

La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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

Best Western Plus Hotel & Conference Center

Historic Inns of Annapolis

Hampton Inn Baltimore/Glen Burnie

Holiday Inn Express White Marsh, An IHG Hotel

Fairfield Inn & Suites by Marriott White Marsh

Frequently asked questions