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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Outdoor banquet area

Lodge in Chestertown

The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is NZ$213
includes taxes & fees
22 Mar - 23 Mar
The Lodge at Great Oak Landing
Exterior

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is NZ$271
includes taxes & fees
23 Mar - 24 Mar
First Floor Studio Apartment in Historic Chestertown
Exterior

Hotel in Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (887 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is NZ$202
includes taxes & fees
22 Mar - 23 Mar
Comfort Inn & Suites Chestertown
Exterior

Hotel in Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (430 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is NZ$128
includes taxes & fees
5 Apr - 6 Apr
Red Roof Inn & Suites Chestertown
Front of property

Bed & Breakfast in Historic District

Flag House Inn
3.5 star property
9.2 out of 10, Wonderful, (89 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is NZ$358
includes taxes & fees
22 Mar - 23 Mar
Flag House Inn
Exterior

Hotel in Grasonville

Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NZ$177
includes taxes & fees
26 Mar - 27 Mar
Best Western Kent Narrows Inn
Fridge, microwave, oven, stovetop

Houseboat in Baltimore

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, (12 reviews)
"Very clean first off I would’ve ate off the floor. Honestly these people have to love what they do to deliver such a 5 star experience "
United States
Anonymous traveller
The price is NZ$1,010
includes taxes & fees
23 Mar - 24 Mar
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Exterior

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$706
includes taxes & fees
20 Mar - 21 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is NZ$550
includes taxes & fees
20 Mar - 21 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

Hotel in Smyrna

Quality Inn Smyrna
2.5 star property
7.6 out of 10, Good, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is NZ$153
includes taxes & fees
29 Mar - 30 Mar
Quality Inn Smyrna
Exterior

Holiday Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is NZ$549
includes taxes & fees
22 Mar - 23 Mar
Large 2 bedroom house with private parking in a nice neighborhood
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$446
includes taxes & fees
23 Mar - 24 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$214
includes taxes & fees
23 Mar - 24 Mar
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$490
includes taxes & fees
20 Mar - 21 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior

Hotel in Annapolis

134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Exterior

Holiday Home in Perryville

5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is NZ$885
includes taxes & fees
25 Mar - 26 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
Property grounds

Holiday Home in Glen Burnie

Secluded Tiny Pool House -Private Pool -Self Check in
8.6 out of 10, Excellent, (10 reviews)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
Secluded Tiny Pool House -Private Pool -Self Check in
Exterior detail

Apartment in Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (203 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is NZ$353
includes taxes & fees
23 Mar - 24 Mar
Cozy Fells Point Gem / In The Heart of Fells Point
Interior

Holiday Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (94 reviews)
"Awesome place, great location"
United States
Mark M.
The price is NZ$347
includes taxes & fees
22 Mar - 23 Mar
Hidden Fells Point Gem / Private Courtyard Patio
Exterior detail

Bed & Breakfast in Havre De Grace

Vandiver Inn
3.5 star property
9.4 out of 10, Exceptional, (536 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
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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Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Establishment was nice, great service, friendly staff, definitely would stay there again. Highly recommend "
Quanda 1-night trip
Posted 9 hours ago
Fairfield Inn & Suites by Marriott White Marsh

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
4,555
Accommodation
2 Cabin Rentals
Lowest Price
NZ$128
Highest Price
NZ$1,010

Frequently asked questions

What are the best cabins near Chestertown?
Book one of our 33 cabins in Chestertown and you'll be rewarded with picturesque scenery, outdoor adventure and memories you'll never forget. Cosy Cabin Happiness is the place to go for a relaxing getaway. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is also ideal if you'd love some time out in Mother Nature.
Are there cheap cabins in Chestertown?
For a budget-friendly escape in nature, look no further than our cheap cabins in Chestertown. Wake up in the morning to the sweet sound of birds chirping from one of our cosy retreats priced from NZ$128 to NZ$1,010 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best family cabins near Chestertown?
If you're seeking a getaway the kids will go wild for, a family cabin rental in or near Chestertown is ideal. Spend time with the gang at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. It offers a meal delivery service and a travel crib as well as ample outdoor adventure. Country Coziness - Lancaster County Private Cabin is another top pick for small groups or families and comes with a deck and a toaster.
What are the best river cabins near Chestertown?
When you think of the word relaxing, a river cabin near Chestertown should be the first thing that comes to mind. Cabin - - Picturesque Wooded Property With Unique Tiny House is the perfect place to discover your Zen. On top of its beautiful surroundings, it features amenities such as on-site watersports and outdoor furniture. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another appealing option. On-site watersports and a firepit are a few of the conveniences that await you here.
What are the best cabins with pools near Chestertown?
If you love the thought of every day being a pool day, escape to Country Coziness - Lancaster County Private Cabin. It's one of our leading cabin rentals with a pool near Chestertown and comes with handy amenities like a swimming pool and a patio. Amazing Getaway: Enjoy Our Cosy Log Cabins On The Chesapeake Bay is another fantastic place to spend your days splashing around. A swimming pool, a patio and good times are all on the menu here.
What are some great Chestertown cabins?
From chic pads with all the fancy perks to cosy retreats that are easy on the hip pocket, Expedia has cabin rentals to suit every taste and budget. Spend a few days enjoying Mother Nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Conveniences here include a firepit and a fireplace. Another excellent option is Pet - Friendly Lakeview Cabin W. It features a deck, a dock and more.
What are the best weekend cabin rentals in Chestertown?
Nothing's as good as a weekend cabin getaway after a tiring week at work. Ditch your cubicle for a few days in nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. A patio and a firepit are among the amenities it offers. Emails will also be the furthest thing from your mind at Country Coziness - Lancaster County Private Cabin. Put your bags down here and make the most of a swimming pool and a patio.
What are the best cabin prices in Chestertown?
With prices starting at just NZ$128 a night for a cabin rental in Chestertown, there's no need to wrestle with that hard-to-pitch tent.
Can I find log cabins in Chestertown?
Kick off your day with a hot coffee in your peaceful log cabin and then try some surfing and swimming. Sound perfect to you? Book a stay at 1850 Historic Log Cabin. Another getaway that comes with lots of character and comfort is Log Cabin In Townsend Delaware. Nearby activities like sea kayaking and hiking will add to the good times here.
What are the highest-rated cabins in Chestertown?
There are some cabin stays that are just about perfect. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a prime example. With an impressive rating, it comes with useful amenities such as a patio, a firepit and loads more. Another terrific option is Pet - Friendly Lakeview Cabin W. A patio and a firepit are a few of the conveniences you'll appreciate here.
What are the top things to see and do in Chestertown?
If you're looking to do some sightseeing around Chestertown, don't miss Washington College. Feeling adventurous? Pick up a car rental and find your way to attractions a little further out, including Rolphs Wharf Marina. There's an amazing world to enjoy beyond your comfortable cabin!
Why should I book a cabin in Chestertown?
For a holiday in the great outdoors at an amazing price, there's nothing better than a cabin. Imagine rising to the sound of birds outside and sipping coffee on a private deck surrounded by stunning vistas. Stay in a cabin in Chestertown to get away from the hectic pace of the city. Whether they're by the beach, in the mountains or near a river, cabins offer a rustic and relaxing experience you'll always remember.
What are the top nature cabins in Chestertown?
Stay at Cabin - - Picturesque Wooded Property With Unique Tiny House and you'll be surrounded by breathtaking nature. Amenities such as on-site watersports and a firepit help make this river cabin in Chestertown a popular choice. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another place where you can escape the concrete jungle and unwind by the river. Conveniences here include on-site watersports and a patio.