Hot Chestertown Guest House Rates

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 Guest Houses in Chestertown

Island Life!  Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville
Located in Stevensville, this guesthouse is on the waterfront, within a 10-minute drive of Paul Reed Smith Guitars and Island Dog Park.
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Second Floor East Standard Deluxe

Second Floor East Standard Deluxe

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Second Floor East Standard Deluxe is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Second Floor East Standard Deluxe
Top Floor Family Deluxe Bay View

Top Floor Family Deluxe Bay View

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Top Floor Family Deluxe Bay View is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Family Deluxe Bay View
Save an average of 15% on thousands of hotels when you're signed in
Calico Cottage Guest House

Calico Cottage Guest House

Annapolis
With a stay at this guesthouse in Annapolis, you'll be on a river, within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Calico Cottage Guest House
Top Floor East Handicap Accessible

Top Floor East Handicap Accessible

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Top Floor East Handicap Accessible is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor East Handicap Accessible
Top Floor Family Deluxe

Top Floor Family Deluxe

2.5 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Top Floor Family Deluxe is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Family Deluxe
Top Floor Standard Suite

Top Floor Standard Suite

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Top Floor Standard Suite is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Standard Suite
Top Floor Handicap Accessible Bay View

Top Floor Handicap Accessible Bay View

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Top Floor Handicap Accessible Bay View is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Handicap Accessible Bay View
Second Floor Standard Deluxe Bay View

Second Floor Standard Deluxe Bay View

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Second Floor Standard Deluxe Bay View is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Second Floor Standard Deluxe Bay View
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.

Guest House Accommodation in Chestertown

We’ve got some pretty great guest house accommodation options in Chestertown, if we do say so ourselves. Even better: they won’t break the bank. So if you’re the type of person who loves a good deal, but also loves your creature comforts, Chestertown guest houses could be for you.

Think of the cosiest possible things you can right now: Loads and loads of blankets on a chilly morning. Fresh flowers in the morning sunlight. Fluffy bathrobes and crackling fireplaces. You get the idea. Guess what? Guest houses in Chestertown have so many options to choose from, you just might find one with all those things. (You should still bring your fave ugg boots though, because they’re just so perfectly broken in.) Yes, your room will be so comfy, you’re gonna want to hole up and hibernate, but don’t give in to the temptation. There are loads of things to do in Chestertown—places to go, people to meet, and food to eat. And no, you can’t bring the fluffy bathrobe with you.

You’ll find the best budget guesthouses right here on lastminute.com.au, so you can take the guesswork out of your holiday.

Chestertown Guest Houses essential information

Accommodation
17 Guest Houses
Lowest Price
AU$123
Highest Price
AU$225
Popular accommodation
Island Life! Kent Island Waterfront with Pool-Bring your boat!, Second Floor East Standard Deluxe, Top Floor Family Deluxe Bay View, Calico Cottage Guest House, Top Floor East Handicap Accessible, Top Floor Family Deluxe, Top Floor Standard Suite, Top Floor Handicap Accessible Bay View, Second Floor Standard Deluxe Bay View

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 AU$193 per night from 17 Aug to 18 Aug
AU$193
17 Aug - 18 Aug
includes taxes & fees
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
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$123 per night from 20 Aug to 21 Aug
AU$123
20 Aug - 21 Aug
includes taxes & fees
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
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 refundableReserve now, pay when you stay
The price is AU$225 per night from 24 Aug to 25 Aug
AU$225
24 Aug - 25 Aug
includes taxes & fees
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
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.