Search the Best Cabins in Chestertown

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In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Outdoor banquet area

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
$124 nightly
The price is $137
Mar 16 - Mar 17
Total with taxes and fees
The Lodge at Great Oak Landing
Exterior

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
$144 nightly
The price is $159
Mar 9 - Mar 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Exterior

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (879 reviews)
"Polite and kind hotel manager"
United States
Richard
$101 nightly
The price is $112
Mar 15 - Mar 16
Total with taxes and fees
Comfort Inn & Suites Chestertown
Exterior

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (429 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
$81 nightly
The price is $90
Mar 10 - Mar 11
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Exterior

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,004 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
$94 nightly
The price is $104
Mar 8 - Mar 9
Total with taxes and fees
Best Western Kent Narrows Inn
Fridge, microwave, oven, stovetop

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
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 traveler
$518 nightly
The price is $601
Mar 9 - Mar 10
Total with taxes and fees
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Basic Double or Twin Room | Desk, free WiFi, bed sheets

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.8 out of 10, Good, (11 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
$49 nightly
The price is $55
Mar 8 - Mar 9
Total with taxes and fees
Motel Edgewood
Exterior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
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.
$280 nightly
The price is $319
Mar 5 - Mar 6
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Exterior

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (13 reviews)
"Great experience"
United States
David P.
$303 nightly
The price is $345
Mar 16 - Mar 17
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Exterior

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
$284 nightly
The price is $314
Mar 5 - Mar 6
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Exterior

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$259 nightly
The price is $286
Mar 5 - Mar 6
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
$262 nightly
The price is $277
Mar 8 - Mar 9
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$261 nightly
The price is $276
Mar 10 - Mar 11
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior detail

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
$196 nightly
The price is $208
Mar 9 - Mar 10
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
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.
$118 nightly
The price is $125
Mar 24 - Mar 25
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,004 reviews)
"Great stay"
United States
Edward
$81 nightly
The price is $90
Mar 10 - Mar 11
Total with taxes and fees
Quality Inn Smyrna
Exterior

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
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.
$494 nightly
The price is $524
Mar 5 - Mar 6
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (351 reviews)
"Consistently a good stay here with helpful staff and comfortable rooms. "
United States
Mary
$99 nightly
The price is $110
Mar 15 - Mar 16
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94 reviews)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
$184 nightly
The price is $213
Mar 8 - Mar 9
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
Exterior

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
$331 nightly
The price is $377
Mar 5 - Mar 6
Total with taxes and fees
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Was at Governor Calvert House. Beautiful historic building that is well maintained. Room was clean and comfortable. Parking is minimal, and valet parking is quite expensive, with "dynamic pricing". Hotel is walking distance to many shops and restaurants. Staff was pleasant and accommodating. "
E Wayne 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
4,274
Accommodation
2 Cabin Rentals
Lowest Price
$55
Highest Price
$601

Frequently asked questions

What are the best cabins near Chestertown?
Rediscover the great outdoors without giving up the comforts at one of our 33 cabins in and around Chestertown. Whether you have relaxation or fun on your itinerary, Cozy Cabin Happiness has lots of both. Alternatively, get cozy at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay and enjoy staring out at its wonderful natural surroundings.
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 cozy retreats priced from $55 to $601 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?
Treat the youngsters to their best vacation yet in one of our Chestertown family cabins. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a top pick. It comes with loads of amenities to make you and your gang feel right at home, including a meal delivery service and a travel crib. Or you can create some marvelous new memories together at Country Coziness - Lancaster County Private Cabin. A deck and a toaster are some of the conveniences to take advantage of here.
What are the best river cabins near Chestertown?
Spend your days kicking back near the water and your evenings listening to it trickling past at a river cabin near Chestertown. Leading our list is Cabin - - Picturesque Wooded Property With Unique Tiny House. This riverside property comes with on-site watersports and outdoor furniture. Or, spend your break at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Along with its picturesque location, highlights here include on-site watersports and a firepit.
What are the best cabins with pools near Chestertown?
Put on your swimwear and enjoy a relaxing dip whenever the mood strikes when you select one of our cabin rentals with a pool. Country Coziness - Lancaster County Private Cabin is a favorite. A swimming pool and a patio are some of the other amenities that'll help make your stay comfortable. Or you can spend your getaway at Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay. As well as a lovely pool, this cabin comes with a swimming pool and a patio.
What are some great Chestertown cabins?
When you want to spend your vacation surrounded by nature but don't feel like roughing it, a cabin is a smart choice. Escape to Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This top pick comes with a firepit, a fireplace and more. Alternatively, experience comfort and outdoor fun at the same time at Pet - Friendly Lakeview Cabin W. A deck and a dock are among this retreat's amenities.
What are the best weekend cabin rentals in Chestertown?
Whether you're planning a mini break with your other half or your close friends, we'll help you locate the perfect weekend cabin getaway. One of our favorites? Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Featuring a patio and a firepit, you'll adore being close to nature here. Country Coziness - Lancaster County Private Cabin is another good place where you can hit pause on life. Enjoy a few nights at this escape which offers a swimming pool and a patio.
Can I find log cabins in Chestertown?
Begin your day with a hot coffee in your cozy log cabin and then go shore fishing and boating. Sound like your dream vacation? Head for 1850 Historic Log Cabin. Another relaxing retreat offering ample charm and comforts is Log Cabin In Townsend Delaware. Close-by activities like stand-up paddle boarding and shore fishing will add to the good times here.
What are the highest-rated cabins in Chestertown?
There are some places that are great in every way. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is one of them. With such an impressive rating, it comes with useful amenities like a patio, a firepit and more. Another excellent option is Pet - Friendly Lakeview Cabin W. A patio and a firepit are just a couple of the conveniences you'll find 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 farther out, including Rolphs Wharf Marina. There's an amazing world to enjoy beyond your comfortable cabin!
Why should I book a cabin in Chestertown?
Affordability, outdoor activities, rustic charm — there's no end of good reasons to choose a Chestertown cabin. Leave behind the clamor of the concrete jungle and rise with the sound of songbirds and wildlife. There's so much adventure just around the corner too. Whether you're vacationing with family members, friends or your sweetheart, you'll discover the perfect rental cabin on Expedia.
What are the top nature cabins in Chestertown?
Our nature cabins in Chestertown come in many shapes and budgets, but there's one thing they all share — unparalleled access to the great outdoors. Cabin - - Picturesque Wooded Property With Unique Tiny House is a magnet for nature lovers. Amenities such as a spa tub and a firepit only make it more appealing. Whether you want to get your feet moving or just put them up, do it at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Another great option, it comes with on-site watersports and a patio.

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