Hot Chestertown Cottage Rates

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Chestertown Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chestertown will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chestertown definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chestertown, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chestertown Cottages essential information

Accommodation
Cottages
Lowest Price
AU$121
Highest Price
AU$660
Popular accommodation
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock , Sagamore Pendry Baltimore

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$190 per night from 25 Dec to 26 Dec
AU$190
includes taxes & fees
25 Dec - 26 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$121 per night from 1 Jan to 2 Jan
AU$121
includes taxes & fees
1 Jan - 2 Jan 2025
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
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Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$660 per night from 12 Jan to 13 Jan
AU$660
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at Sagamore Pendry Baltimore in Baltimore (Fells Point), you'll be within a 5-minute drive of Johns Hopkins Hospital and National Aquarium in ...
Sagamore Pendry Baltimore
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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.