Book Holiday Homes in Chestertown

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chestertown

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
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Love Point State Park and 7 minutes from Paul Reed Smith Guitars.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Captivating Chesapeake experience

Captivating Chesapeake experience

Perryville
Located in Perryville, this vacation home is on the waterfront, a 4-minute drive from Chestnut Point Estates and Marina and 5 minutes from Craft Haven ...
Captivating Chesapeake experience
Save an average of 15% on thousands of hotels when you're signed in
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
The price is AU$417 per night from 7 Apr to 8 Apr
AU$417
includes taxes & fees
7 Apr - 8 Apr
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.
Historic Annapolis Home 1.5 blocks from center of town.
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

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

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Entire House by the Fells Point, JHU.

Entire House by the Fells Point, JHU.

Baltimore
With a stay at this vacation home, you'll be centrally located in Baltimore, within a 5-minute drive of National Aquarium in Baltimore and Baltimore Convention ...
Entire House by the Fells Point, JHU.
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 out of 5
Annapolis
Steps to USNA Gate 3 at historic Gatehouse, on-site parking is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval ...
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and John Smith House.
PERFECT LOCATION in the heart of history
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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
528 Holiday Homes
Lowest Price
AU$121
Highest Price
AU$417
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, Captivating Chesapeake experience, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Entire House by the Fells Point, JHU., Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history

Top trending hotels in 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 AU$121 per night from 10 Apr to 11 Apr
AU$121
includes taxes & fees
10 Apr - 11 Apr
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Chestertown Dog Park.
Red Roof Inn & Suites 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 AU$207 per night from 4 May to 5 May
AU$207
includes taxes & fees
4 May - 5 May
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical ...
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is AU$235 per night from 4 May to 5 May
AU$235
includes taxes & fees
4 May - 5 May
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for ...
The Lodge at Great Oak Landing
Save an average of 15% on thousands of hotels when you're signed in
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$318 per night from 13 Apr to 14 Apr
AU$318
includes taxes & fees
13 Apr - 14 Apr
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.