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Find Resorts & Hotels with Spas in Chestertown, MD

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Pick from 17 Chestertown Resorts & Hotels with Spas and compare room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Exterior

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is SAR 401
SAR 442 total
includes taxes & fees
15 Dec - 16 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (320)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is SAR 280
SAR 308 total
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

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

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is SAR 368
SAR 592 total
includes taxes & fees
30 Nov - 1 Dec
First Floor Studio Apartment in Historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
looking down river from the dock

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Welcome to Harbor View Haven- A luxurious getaway home with gorgeous views!

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

10.0 out of 10, Exceptional, (15)
"My family enjoyed this house so much. The place is perfect for a relaxing gateway with so much peace and nature. Will definitely be back!"
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Front Porch

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (64)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Eastern Shore Getaway: Walk to Tolchester Marina!
Chestertown Vacation Rental | 5BR | 2.5BA | 2,500 Sq Ft | Stairs Required

Eastern Shore Getaway: Walk to Tolchester Marina!

10.0 out of 10, Exceptional, (2)
"Beautiful home and great hospitality. Very clean and smelled amazing (that's important for people who have sensitivity to smells). Comfy beds too. "
Eastern Shore Getaway: Walk to Tolchester Marina!
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Welcome to Langford Creek Estate- a beautiful waterfront estate with an extensive amenity list!

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

9.2 out of 10, Wonderful, (5)
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
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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Frequently asked questions

Looking for a spa hotel in Chestertown?
Soothe the senses with some time in one of our wonderful spa hotels. Check out the historical sites and art galleries in Chestertown—your cultural tour starts here. Hotels with spas are the perfect way to take a break from your routine and add a layer of luxury to your vacation.
How many spa hotels will I find in Chestertown?
Among Expedia’s 26 accommodation options in Chestertown, there is 1 spa hotel.
What's there to see and do in Chestertown?
Experience all that Chestertown has to offer when you visit Rolphs Wharf Marina, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater. If you have a little extra time during your trip, you might want to check out Wilmer Park and Crumpton Auction.
What is a Chestertown spa hotel?
Spa hotels in Chestertown provide lodging and have an on-site spa offering services including massages and body treatments. Some also offer in-room treatments. Spa hotels are great for rest, rejuvenation, and relaxation.