Hot Chestertown Guest House Rates

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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 MD
Located in Stevensville, this guesthouse is on the waterfront, within a 10-minute drive of Paul Reed Smith Guitars and Chesapeake Bay.
Opens in a new windowIsland 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.
Opens in a new windowSecond 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.
Opens in a new windowTop Floor Family Deluxe Bay View
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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.
Opens in a new windowTop Floor East Handicap Accessible
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.
Opens in a new windowTop Floor Standard Suite
The Shallow Creek Shore Shack on the Chesapeake Bay

The Shallow Creek Shore Shack on the Chesapeake Bay

Sparrows Point MD
When you stay at this guesthouse in Edgemere, you'll be on the waterfront, within a 5-minute drive of Patapsco River and Chesapeake Bay.
Opens in a new windowThe Shallow Creek Shore Shack on the Chesapeake Bay
First Floor Family Deluxe Suite

First Floor Family Deluxe Suite

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

First Floor Bay View Deluxe Suite

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

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$120
Highest Price
AU$170
Popular accommodation
Island Life! Kent Island Waterfront with Pool-Bring your boat!, Second Floor East Standard Deluxe, Top Floor Family Deluxe Bay View, Top Floor East Handicap Accessible, Top Floor Standard Suite, The Shallow Creek Shore Shack on the Chesapeake Bay, First Floor Family Deluxe Suite, Second Floor Standard Deluxe Bay View, First Floor Bay View Deluxe Suite

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$170 per night from 21 Dec to 22 Dec
AU$170
21 Dec - 22 Dec
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 ...
Opens in a new windowComfort 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$120 per night from 22 Dec to 23 Dec
AU$120
22 Dec - 23 Dec
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.
Opens in a new windowRed 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 refundable
The price is AU$170 per night from 18 Dec to 19 Dec
AU$170
18 Dec - 19 Dec
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 ...
Opens in a new windowThe Lodge at Great Oak Landing
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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.
Opens in a new windowHistoric Inns of Annapolis
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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.