Hot Chestertown Bed & Breakfast 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 B&B in Chestertown

Vandiver Inn

Vandiver Inn

3.5 out of 5
301 South Union Avenue, Havre De Grace, MD
With a stay at Vandiver Inn, you'll be centrally located in Havre De Grace, just a 4-minute walk from Harford Memorial Hospital and 9 minutes by foot from Susquehanna ...
Vandiver Inn
Naomi Bed & Breakfast

Naomi Bed & Breakfast

3 out of 5
9907 Harford Rd, Parkville, MD
Located in Parkville, Naomi Bed & Breakfast is within a 10-minute drive of Goucher College and White Marsh Mall.
Naomi Bed & Breakfast
Flag House Inn

Flag House Inn

3.5 out of 5
26 Randall St, Annapolis, MD
The price is AU$314 per night from 26 Nov to 27 Nov
AU$314
includes taxes & fees
26 Nov - 27 Nov
With a stay at Flag House Inn, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Flag House Inn
Save an average of 15% on thousands of hotels when you're signed in
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 out of 5
4928 Eastern Neck Rd, Rock Hall, MD
The price is AU$335 per night from 26 Nov to 27 Nov
AU$335
includes taxes & fees
26 Nov - 27 Nov
Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor.
Inn at Huntingfield Creek
Private room for one person 18+ years only. Text for availability 973-477-4574

Private room for one person 18+ years only. Text for availability 973-477-4574

Dover
A stay at this bed & breakfast places you in the heart of Dover, within a 5-minute drive of Fork Branch Nature Preserve and Greentree Village Shopping ...
Private room for one person 18+ years only. Text for availability 973-477-4574
The Annapolis Inn

The Annapolis Inn

4 out of 5
144 Prince George St, Annapolis, MD
With a stay at The Annapolis Inn in Annapolis (Historic District), you'll be steps from U.S. Naval Academy and John Smith House.
The Annapolis Inn
Surf Condominiums - Downtown Bethany

Surf Condominiums - Downtown Bethany

Baltimore
With a stay at this bed & breakfast in Baltimore (Bayview), you'll be within a 10-minute drive of Baltimore Cruise Terminal and Baltimore Inner Harbor ...
Surf Condominiums - Downtown Bethany
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.

B&Bs in Chestertown

We know why you’re here. You forgot something, though we’re not sure what. A birthday or an anniversary, maybe. And this time, a bouquet of fresh flowers and a homemade breakfast in bed aren’t going to cut it. You’re determined your special someone is going to feel like the centre of the universe on whatever special day you have coming up—that’s where lastminute.com.au comes in, and that’s also where Chestertown B&B accommodation comes in.

You can’t go wrong with a romantic getaway to a bed and breakfast. It’s the stuff of poetry, novels, and of course, any good rom-com. You can snuggle under the covers all morning if you like, although the delicious aromas of a home-cooked breakfast are likely to get you out of bed. Even a cheap B&B will have a delectable morning meal included—and you don’t have to make it yourself. After all, that’s kind of the whole point. Add in a boutique feel and the charming Chestertown vibes, and you’ll get why B&Bs are great for couples, families, and even your doggo. Yes, pet-friendly B&Bs are a thing, and although we can’t guarantee the dog will get his own breakfast, you’re more than happy to share, aren’t you?

Hey, if you’re gonna stay in a B and B in Chestertown, you want it to be awesome, don’t you? Well then, check out lastminute.com.au and get to planning. We’ve got everything from luxury to budget bed & breakfasts, and our great prices leave you plenty of cash to splash in Chestertown. No need to thank us—we know how great we are.

Chestertown B&B essential information

Accommodation
7 B&B
Lowest Price
AU$128
Highest Price
AU$335
Popular accommodation
Vandiver Inn, Naomi Bed & Breakfast, Flag House Inn, Inn at Huntingfield Creek, Private room for one person 18+ years only. Text for availability 973-477-4574, The Annapolis Inn, Surf Condominiums - Downtown Bethany

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$180 per night from 10 Dec to 11 Dec
AU$180
includes taxes & fees
10 Dec - 11 Dec
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$128 per night from 2 Dec to 3 Dec
AU$128
includes taxes & fees
2 Dec - 3 Dec
You'll be centrally located in Chestertown with a stay at Red Roof Inn & Suites Chestertown, and 11 minutes by foot from Washington College.
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Chestertown
Located in Chestertown, this vacation home is on the waterfront, within a 15-minute drive of Washington College and Garfield Center for the Arts at the Prince ...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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$246 per night from 27 Nov to 28 Nov
AU$246
includes taxes & fees
27 Nov - 28 Nov
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.