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Find Resorts & Hotels with Spas in Chestertown, MD

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Check availability on Chestertown Resorts & Hotels with Spas

Compare Chestertown Resorts & Hotels with Spas 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, (745)
"Staff was courteous and friendly. Room was clean and in good order. Check out was quick and very easy."
The price is SAR 400
SAR 444 total
includes taxes & fees
17 Mar - 18 Mar
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (332)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
The price is SAR 270
SAR 300 total
includes taxes & fees
28 Feb - 1 Mar
Red Roof Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is SAR 368
SAR 592 total
includes taxes & fees
26 Feb - 27 Feb
First Floor Studio Apartment in Historic Chestertown
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, (16)
"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!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Exterior

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (75)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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
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)
"Very clean, tidy home directly on the Chester river. While we were here for an event at Washington College in February, the property is gorgeous and we definitely want to return during warmer months to enjoy Chestertown and sipping wine on the deck overlooking the river. The house has lots of seating throughout and we enjoyed playing card games at night with the kids. Super clean house, and kitchen is incredibly functional. Can't wait to return!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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!
Goose Landing on Fairlee Creek

Goose Landing on Fairlee Creek

9.8 out of 10, Exceptional, (18)
"We were a group of three pair of brothers, all cousins/nephews to one another. We go annually to the Chesapeake Bay area for a weekend of crabbing and fishing. This year we stayed here for 4 nights over the weekend. The property is as described and pictured. We had an enjoyable and fun stay here. Plenty of space, both indoors and outdoors, for 6 guys!"
Goose Landing on Fairlee Creek
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, (66)
"This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!"
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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 Kings Town Park.
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.