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
Located in Stevensville, this guesthouse is on the waterfront, within a 10-minute drive of Paul Reed Smith Guitars and Island Dog Park.
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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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.
Opens in a new windowCalico 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.
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
Top Floor Standard Deluxe

Top Floor Standard Deluxe

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

Second Floor Standard Suite Bay View

2 out of 5
60 Sandy Cove Road, North East, MD
Located in North East, Second Floor Standard Suite Bay View is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Opens in a new windowSecond Floor Standard Suite Bay View
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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$136
Highest Price
AU$229
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 Standard Suite, Top Floor Standard Deluxe, Second Floor Standard Deluxe Bay View, Second Floor Standard Suite Bay View

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$136 per night from 14 Oct to 15 Oct
AU$136
14 Oct - 15 Oct
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
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 2 Nov to 3 Nov
AU$193
2 Nov - 3 Nov
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
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$229 per night from 8 Oct to 9 Oct
AU$229
8 Oct - 9 Oct
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.