Book Holiday Homes in Chestertown

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Featured Holiday Homes in Chestertown

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
Stay at this vacation home in Chestertown. Enjoy private pools, a garden, and patios.
Pet-Friendly Home on Chester River w/ Dock!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3 out of 5
3512 Gough Street, Baltimore, MD
Stay at this 3-star vacation home in Baltimore. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Baltimore Inner Harbor Marina ...
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
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Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Chase Lloyd House and Hammond-Harwood ...
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and bar

Centreville
Book a stay at this beach vacation home in Centreville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Earle Landing and Hazel Miner Monument ...
Waterfront family resort Lodge with private pier, game room and bar
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Ellen O. Moyer Nature Park at Back ...
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
A waterfront gem with dock, kayaks great water views.  Sleeps up to 12.

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

Rock Hall
Stay at this vacation home in Rock Hall. Enjoy free WiFi, a garden, and patios. Popular attractions The Mainstay and Rock Hall Harbor are located nearby.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
Stay at this vacation home in Stevensville. Enjoy free WiFi, a garden, and patios. Popular attraction Matapeake State Park is located nearby.
Relax on Kent Island in 3 Bedroom Home w/Waterview
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

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

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the pool in our reviews. Popular attractions ...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
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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.

Chestertown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chestertown vacation homes are the perfect way for you to wing it.

Holiday houses in Chestertown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chestertown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chestertown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chestertown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chestertown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chestertown Holiday Homes essential information

Accommodation
417 Holiday Homes
Lowest Price
NZ$135
Highest Price
NZ$733
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning, Charming garden row home, easy 4 block walk to the heart of Annapolis., Waterfront family resort Lodge with private pier, game room and bar, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Relax on Kent Island in 3 Bedroom Home w/Waterview, 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Top trending hotels in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$208 per night from 6 Jan to 7 Jan
NZ$208
includes taxes & fees
6 Jan - 7 Jan 2025
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 5 Jan to 6 Jan
NZ$135
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews.
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

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

Chestertown
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Historical Society of Kent County Maryland and Garfield ...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Save an average of 15% on thousands of hotels when you're signed in
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is NZ$733 per night from 12 Jan to 13 Jan
NZ$733
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this 5-star luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
Sagamore Pendry Baltimore
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See all available properties in Chestertown
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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.

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^Subject to availability and chosen travel dates.