Top Chestertown Villa Rates

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Featured Villas in Chestertown

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall
Located in Rock Hall, this villa is on the waterfront, within a 10-minute drive of The Mainstay and Rock Hall Harbor.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12

LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12

Chester
With a stay at this villa in Chester, you'll be within a 15-minute drive of Chesapeake Exploration Center and Island Dog Park.
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Stunning waterfront villa with indoor pool and kids swing set and play area.

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
With a stay at this villa in Earleville, you'll be 9.7 mi (15.6 km) from Bohemia Vista Marina and 10.4 mi (16.7 km) from C and D Canal Museum.
Stunning waterfront villa with indoor pool and kids swing set and play area.
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Blake House Historic Estate with Private Inn

Blake House Historic Estate with Private Inn

Centreville
Located in Centreville, this villa is on the waterfront, within a 15-minute drive of Hazel Miner Monument and Earle Landing.
Blake House Historic Estate with Private Inn
Exquisite 14,000 sq ft Waterfront Mansion with Pool

Exquisite 14,000 sq ft Waterfront Mansion with Pool

Stevensville
With a stay at this villa in Stevensville, you'll be within a 5-minute drive of Love Point State Park and Paul Reed Smith Guitars.
Exquisite 14,000 sq ft Waterfront Mansion with Pool
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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.

Chestertown Luxury Villas

It’s time to plan your next getaway, and this time, you want it to be amazing. You just want a holiday where you’ll come away with humble brags like “I just couldn’t choose between the pool or the hot tub” and “It was so hard for the whole family to pick their rooms in such a big house”. OK, maybe those aren’t so humble. And that’s exactly the point when you’ve got Chestertown villa accommodation from lastminute.com.au.

You know what else you might get with that villa? A gourmet kitchen. What does one do in a gourmet kitchen? Why, craft delicious meals that are bound to impress your significant other, kiddos, mum, or whoever else you count among your travelling companions. Nothing says “clan getaway” like a tasty dinner in luxey surroundings, after all. But who says you even have to cook? Conjuring up gastronomic delights takes effort, and you ask us, cheap villa holidays are all about relaxing—and enjoying the fact you’re getting so much bang for your buck. Chestertown has plenty of ways to delight your taste buds, and don’t get us started on the scenery. No filter, indeed.

Yes, this holiday will give you plenty of humble brags, but there’s nothing humble at all about our awesome deals. Put in for some annual leave and grab some pocket change, because we’ve got Chestertown villas that will have you wondering “How is that even possible?” Anything is possible—well, almost anything—when you’ve got lastminute.com.au on your side.

Chestertown Villas essential information

Accommodation
5 Villas
Lowest Price
AU$121
Highest Price
AU$660
Popular accommodation
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna, LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12, Stunning waterfront villa with indoor pool and kids swing set and play area. , Blake House Historic Estate with Private Inn, Exquisite 14,000 sq ft Waterfront Mansion with Pool

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
Save an average of 15% on thousands of hotels when you're signed in
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.