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Cabin Rentals in Chestertown

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Recommended hotels in Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (855)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$102 nightly
The price is $113
Nov 30 - Dec 1
Total with taxes and fees
Comfort Inn & Suites Chestertown

Lodge in Chestertown

3.5 star property
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Nov 26 - Nov 27
Total with taxes and fees
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (417)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
$72 nightly
The price is $80
Dec 1 - Dec 2
Total with taxes and fees
Red Roof Inn & Suites Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Nov 26 - Nov 27
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

Motel in Chestertown

2.0 star property
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
$64 nightly
The price is $70
Dec 24 - Dec 25
Total with taxes and fees
Driftwood Inn

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1008)
"Would stay again"
United States
Dena
$82 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (592)
"Wonderful room and location "
United States
Caren
$90 nightly
The price is $101
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.4 out of 10, Good, (1021)
"Staff was very friendly. "
United States
Ashlee
$63 nightly
The price is $71
Nov 26 - Nov 27
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (306)
"Great overall experience "
United States
Clement
$105 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1012)
"The room was nice the bed comfy, the staff was friendly "
United States
Kenya
$93 nightly
The price is $104
Nov 30 - Dec 1
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (642)
"This was a great relaxing stay"
United States
Pamela
$103 nightly
The price is $115
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG

Quality Inn

2.5 star property
7.6 out of 10, Good, (1002)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
$68 nightly
The price is $75
Dec 1 - Dec 2
Total with taxes and fees
Quality Inn

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

3.0 star property
8.8 out of 10, Excellent, (1007)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
$86 nightly
The price is $96
Dec 21 - Dec 22
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Motel in Aberdeen

2.0 star property
7.0 out of 10, Good, (855)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
$50 nightly
The price is $56
Dec 15 - Dec 16
Total with taxes and fees
Super 8 by Wyndham Aberdeen MD

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1005)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$92 nightly
The price is $102
Dec 1 - Dec 2
Total with taxes and fees
Best Western Kent Narrows Inn

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (856)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$103 nightly
The price is $115
Dec 1 - Dec 2
Total with taxes and fees
Hampton Inn Middletown

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$119 nightly
The price is $132
Dec 1 - Dec 2
Total with taxes and fees
Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (663)
"My favorite hotel "
United States
Jen
$143 nightly
The price is $159
Nov 30 - Dec 1
Total with taxes and fees
Hyatt Place Kent Narrows & Marina

Fairfield Inn & Suites by Marriott Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (298)
"Great location close to everything we needed"
United States
John
$101 nightly
The price is $113
Nov 30 - Dec 1
Total with taxes and fees
Fairfield Inn & Suites by Marriott Aberdeen

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3.0 star property
8.2 out of 10, Very Good, (1003)
"Very good hotel for the price clean and comfortable "
Canada
Randy
$79 nightly
The price is $88
Nov 26 - Nov 27
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
13,868
Accommodation
3 Cabin Rentals
Lowest Price
$56
Highest Price
$159

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 $56 to $159 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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