Chestertown Holiday Homes

Check availability on Holiday Homes in Chestertown

16 Apr - 17 Apr

Tonight

17 Apr - 18 Apr

Tomorrow night

Featured Holiday Homes in Chestertown

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

Annapolis, MD

£961

per night

20 Apr - 21 Apr

During your stay at Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, you'll be close to Chesapeake Bay Bridge. Enjoy features like a gym, a hot tub and concierge services.

Caribbean Oasis with Pool Home - 25 mins to USNA!

Stevensville, Maryland

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During your stay at Caribbean Oasis with Pool Home - 25 mins to USNA!, you're just a quick walk from Matapeake State Park.

Directly Across from Gate One & Steps from the Waterfront

Annapolis, MD

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Our customers tell us they can't get enough of this holiday home's walkable location. During your stay, you're just a quick walk from U.S. Naval Academy. You'll find features such as a water park. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!

Havre De Grace, MD

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Our customers tell us they can't get enough of this holiday home's great location. During your stay, you're just a quick walk from Susquehanna Museum at the Lock House. A water park is available. The holiday home includes amenities such as free WiFi and a kitchen.

Luxurious Three bedroom fells point townhome with rooftop deck

Baltimore, MD

£331

per night

17 Apr - 18 Apr

Our customers tell us they enjoy this holiday home's good location. During your stay, you're just a quick walk from Patterson Park. The holiday home includes amenities such as a kitchen and 3 bathrooms.

Kitchen

Washer

Sunny Glen Burnie Home - On-Site Water Access

Glen Burnie, Maryland

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During your stay at this holiday home, you'll be close to Bingo World. Enjoy features like free WiFi in public areas. The holiday home includes amenities such as a kitchen and a washer/dryer.

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

Annapolis, MD

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Our customers tell us that they can't get enough of the pool at this holiday home. During your stay, you're just a quick walk from Annapolis Maritime Museum. Free WiFi in public areas, an outdoor pool and a gym are available. Enjoy your stay with amenities like free WiFi and a private pool in the holiday home.

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Baltimore, MD

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During your stay at this holiday home, you're just a quick walk from Patterson Park. The holiday home offers free WiFi and a kitchen.

Private detached 1bedroom guest house.

Glen Burnie, MD

£163

per night

21 Apr - 22 Apr

During your stay at this holiday home, you'll be close to Bingo World. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Steps from the water, Easy parking and private backyard patio

Annapolis, MD

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Our customers tell us they can't get enough of this holiday home's walkable location. During your stay, you're just a quick walk from U.S. Naval Academy. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Stunning Home Steps minutes from Cal Ripken Stadium!!!

Aberdeen, MD

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During your stay at this holiday home, you'll be within walking distance of Cal Ripken Museum. You'll find features such as a hot tub. A jetted bath and a kitchen are available in the holiday home.

Large 2 bedroom house with private parking in a nice neighborhood

Arnold, MD

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During your stay at this holiday home, you'll be close to Bay Hills Golf Club. The holiday home offers free WiFi and a kitchen.

River Breezes with a private pier, parking and billiards room

Severna Park, MD

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During your stay at this holiday home, you'll be close to Severna Park Golf Center. Features include free WiFi in public areas, plus an arcade/games room and self-parking (surcharge). The holiday home includes amenities such as free WiFi and a kitchen.

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis, MD

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The clean homes at this holiday home get high marks from our customers. During your stay, you'll be close to U.S. Naval Academy. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis, MD

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This holiday home's good location gets good marks from our customers. During your stay, you're just a quick walk from Maynard-Burgess House. Free WiFi and a kitchen are available in the holiday home.

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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.

How to Find the Best Holiday Homes in Chestertown

Why rent a holiday home in Chestertown?

Chestertown holiday homes are perfect for lots of travellers and different types of holiday. You’ll have a place to call home, and more space and privacy. There are many accommodations to suit your needs, whether it’s a couples’ getaway or a large house to fit all your friends and family.

What are the benefits of booking a holiday home with ebookers?

ebookers offers some of the best deals on holiday homes in Chestertown. We give our members exclusive discounts with Insider Prices. Plus, members registered with BONUS+ receive points back on every booking (1 point = £1), and there are no blackout dates for using them. Choose from a great selection of holiday homes and get your flight tickets or car hire in Chestertown at the same time to save even more.

How much does it cost to rent a holiday home in Chestertown?

Prices on holiday homes in Chestertown between £163 - £961. Nightly rates vary based on your travel dates, property location, amenities, number of bedrooms, and more.

How many holiday homes can you choose from in Chestertown?

There are 355 private vacation homes available to rent in Chestertown.

What amenities can I find in a private holiday home?

Our private rental homes offer a wide range of amenities. Discover holiday homes with a swimming pool, games room, air-conditioning, hot tub, parking, and other desirable features. You can use our filters to narrow down your search.

When is the best time to stay in a holiday home in Chestertown?

Prices for Chestertown rental houses change based on seasonal demand. They are cheapest during and highest during . Save money by booking a stay during the low season, . You can also plan your stay during the high season, , to take advantage of the weather and fun activities.

How do I find the best price on a holiday home in Chestertown?

On ebookers you can easily find some of the best deals on holiday homes in Chestertown. Choose an offer that interests you and enter your travel dates to see the exact price. You can explore different neighbourhoods and compare costs within the area using our map feature. Adjust your travel dates to view prices for similar timeframes and use our filters to narrow down your search.

Does ebookers offer flexible bookings or holidays homes with free cancellation?

It’s important to keep in mind the terms of each deal during your search. Some bookings offer free cancellation while others are non-refundable. For holiday homes in Chestertown, cancellations must go through the individual property owner. To find out more about your reservation, navigate to your itinerary. For all other questions and concerns, please visit our customer service portal.

Chestertown Holiday Homes essential information

Accommodation	355 Holiday Homes
Lowest Price	£163
Highest Price	£961
Popular accommodation	Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Caribbean Oasis with Pool Home - 25 mins to USNA!, Directly Across from Gate One & Steps from the Waterfront , Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!, Luxurious Three bedroom fells point townhome with rooftop deck, Sunny Glen Burnie Home - On-Site Water Access, 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented., Private detached 1bedroom guest house., Steps from the water, Easy parking and private backyard patio, Stunning Home Steps minutes from Cal Ripken Stadium!!!, Large 2 bedroom house with private parking in a nice neighborhood, River Breezes with a private pier, parking and billiards room, Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis , Historic Carriage House in the Heart of Downtown Annapolis

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