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
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
Located in Earleville, this villa is a 4-minute drive from Earleville Wildlife Management Area and 9 minutes from Long Point Marina.
Stunning waterfront villa with indoor pool and kids swing set and play area.
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
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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
3 Villas
Lowest Price
AU$119
Highest Price
AU$312
Popular accommodation
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna, Stunning waterfront villa with indoor pool and kids swing set and play area. , Blake House Historic Estate with Private Inn

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$119 per night from 28 Apr to 29 Apr
AU$119
includes taxes & fees
28 Apr - 29 Apr
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.
Red 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$192 per night from 4 May to 5 May
AU$192
includes taxes & fees
4 May - 5 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 ...
Comfort 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 refundable
The price is AU$209 per night from 22 Apr to 23 Apr
AU$209
includes taxes & fees
22 Apr - 23 Apr
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 ...
The 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
The price is AU$312 per night from 29 Apr to 30 Apr
AU$312
includes taxes & fees
29 Apr - 30 Apr
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
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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.