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Search the Best Cabins in Chestertown

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (989 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
$100 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites Chestertown
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (504 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
United States
Linda
$72 nightly
The price is $80
Oct 11 - Oct 12
Total with taxes and fees
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
$64 nightly
The price is $70
Oct 5 - Oct 6
Total with taxes and fees
Driftwood Inn
A building with a balcony and large windows, surrounded by trees and a fence.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (129 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
$144 nightly
The price is $159
Oct 5 - Oct 6
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A large white tent with a peaked roof, surrounded by a grassy area and potted plants.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (116 reviews)
"This is a wonderful facility for a couple or family. The restaurant is just "ok"."
United States
Sandra
$124 nightly
The price is $137
Oct 7 - Oct 8
Total with taxes and fees
The Lodge at Great Oak Landing
A two-story building with a ground-floor commercial space and upper residential units.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$320 nightly
The price is $353
Oct 7 - Oct 8
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A rustic wooden barn with a red roof, surrounded by lush greenery and a wooden fence.

7. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$264 nightly
The price is $274
Oct 8 - Oct 9
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A house with a blue door, a front porch, and a garden with various plants and flowers.

8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
$291 nightly
The price is $308
Oct 12 - Oct 13
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A two-story house with a porch, a chimney, and a flagpole.

9. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$463 nightly
The price is $481
Oct 7 - Oct 8
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A two-story house with a covered porch, a staircase, and a garden area.

10. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (15 reviews)
"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."
United States
Joe
$135 nightly
The price is $150
Oct 7 - Oct 8
Total with taxes and fees
Haven Point Inn and Gallery
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

11. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
$178 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
Inn at Huntingfield Creek
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

12. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$259 nightly
The price is $286
Oct 5 - Oct 6
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

13. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"Good hotel for the money and location."
United States
Marc
$110 nightly
The price is $122
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

14. 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
9.8 out of 10, Exceptional, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Oct 5 - Oct 6
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A building with a gabled roof and a circular vent on the roof.

15. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$286 nightly
The price is $316
Oct 5 - Oct 6
Total with taxes and fees
BAYSIDE BUNGALOW
A hotel with a modern facade, a covered entrance, and a red car parked outside.

16. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (945 reviews)
"Overall a great place to rest, the check in process was super easy & staff was really helpful. Rooms are spacious and clean. They offer free breakfast in the morning which was also great. I recommend this place to anyone who wants a nice play to stay."
United States
Evelyn
$107 nightly
The price is $124
Oct 11 - Oct 12
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
A multi-story hotel with outdoor seating areas and a dock extending into the water.

17. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (840 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
$152 nightly
The price is $169
Oct 13 - Oct 14
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A Hampton Inn hotel with a modern brick facade, large windows, and a clear blue sky.

18. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,002 reviews)
"Nice room. Nice stay."
United States
Lyn
$85 nightly
The price is $96
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

19. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (981 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
$96 nightly
The price is $107
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,000 reviews)
"Very big room, everything clean. Great location, friendly staff. Would definitely stay here again."
United States
Vanessa
$89 nightly
The price is $100
Nov 1 - Nov 2
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Our room was a little dated and worn, but had all the amenities we care about - comfy bed, good shower, nice towels - and was clean and quiet. Affordable and convenient to highway and shopping, with friendly helpful staff."
Joyce 1-night trip
Posted 14 hours ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
2,986
Accommodation
4 Cabin Rentals
Lowest Price
$70
Highest Price
$481

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 $70 to $481 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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