Hot Chestertown Guest House Rates
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Featured Guest Houses in Chestertown
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.
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.
Top Floor East Handicap Accessible
60 Sandy Cove Road, North East, MD
The price is AU$751 per night from 5 May to 6 May
AU$751
includes taxes & fees
5 May - 6 May
Located in North East, Top Floor East Handicap Accessible is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
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Center Parlor Room at Sandy Cove
60 Sandy Cove Road, North East, MD
The price is AU$792 per night from 6 May to 7 May
AU$792
includes taxes & fees
6 May - 7 May
Located in North East, Center Parlor Room at Sandy Cove is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
First Floor Bay View Deluxe Suite
60 Sandy Cove Road, North East, MD
The price is AU$855 per night from 11 May to 12 May
AU$855
includes taxes & fees
11 May - 12 May
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.
Top Floor Deluxe Suite Bay View
60 Sandy Cove Road, North East, MD
The price is AU$855 per night from 11 May to 12 May
AU$855
includes taxes & fees
11 May - 12 May
Located in North East, Top Floor Deluxe Suite Bay View is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Handicap Accessible Bay View
60 Sandy Cove Road, North East, MD
The price is AU$792 per night from 14 May to 15 May
AU$792
includes taxes & fees
14 May - 15 May
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.
First Floor Family Deluxe Suite
60 Sandy Cove Road, North East, MD
The price is AU$751 per night from 5 May to 6 May
AU$751
includes taxes & fees
5 May - 6 May
Located in North East, First Floor Family Deluxe Suite is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
Top Floor Standard Deluxe
60 Sandy Cove Road, North East, MD
The price is AU$751 per night from 6 May to 7 May
AU$751
includes taxes & fees
6 May - 7 May
Located in North East, Top Floor Standard Deluxe is a 1-minute drive from Roachs Shore and 9 minutes from Upper Bay Museum.
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 | 16 Guest Houses |
|---|---|
Lowest Price | AU$118 |
Highest Price | AU$855 |
Popular accommodation | Island Life! Kent Island Waterfront with Pool-Bring your boat!, Calico Cottage Guest House, Top Floor East Handicap Accessible, Center Parlor Room at Sandy Cove, First Floor Bay View Deluxe Suite, Top Floor Deluxe Suite Bay View, Top Floor Handicap Accessible Bay View, First Floor Family Deluxe Suite, Top Floor Standard Deluxe |
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More accommodations in Chestertown
Top trending hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$118 per night from 13 May to 14 May
AU$118
includes taxes & fees
13 May - 14 May
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.
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 11 May to 12 May
AU$189
includes taxes & fees
11 May - 12 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 ...
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is AU$228 per night from 18 May to 19 May
AU$228
includes taxes & fees
18 May - 19 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 ...
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Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is AU$324 per night from 11 May to 12 May
AU$324
includes taxes & fees
11 May - 12 May
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
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.
More ways to explore Chestertown
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^Subject to availability and chosen travel dates.