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Search the Best Cabins in Chestertown

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Compare 2 Cabin Rentals in Chestertown with updated reviews, rates, and availability.

Property grounds
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (65)
"We had a great get-away for a few days with our friends. The cabin was in a quiet neighborhood with amazing views. We especially enjoyed using the fire pit while sitting in the comfortable Adirondack chairs overlooking the Chesapeake Bay. The owners were friendly and great to work with. Highly recommend!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Beach
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
8.0 out of 10, Very Good, (1)
"This is a cute little cabin. The room was as advertised. The place is also a Christian ministry place. Hotels.com guests should be aware that there are signs on the road in that reference Jesus. We also saw a couple prayer circles. This was not a problem for us. It waa early season so the lovely pools were not open. They send an email with check in directions which were use the lock box. We did not get the email. We went to what looked like a check in area and no one was around. This was quite...
The price is $315
$387 total
includes taxes & fees
Jun 8 - Jun 9
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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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.

Other property types in Chestertown

Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (264)
"Cute little cottage with a beautiful view! Forgot to account for the mini fridge with the food we brought, but besides that, everything went great for our short stay."
The Heron's Nest at Atlantic Marina
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.

Chestertown Cabin Rentals information

Number of reviews
61
Accommodation
2 Cabin Rentals
Lowest Price
$315
Highest Price
$315

Frequently asked questions

What are the best cabins near Chestertown?
Stay in the outdoors without surrendering home comforts at one of our 20 cabins in and around Chestertown. Whether you have relaxation or adventure on your itinerary, Cozy Cabin Happiness delivers plenty of both. Alternatively, head for Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay and nestle yourself among picturesque surroundings.
Are there cheap cabins in Chestertown?
For a memorable escape in the great outdoors, check out our cheap cabins in Chestertown. Wake up each morning to the sound of birdsong from one of our cozy cabin rentals priced from $315 to $315 a 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 hot tub cabins near Chestertown?
If you’re someone who can’t do without a hot tub on vacation, you’ll like Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This charmer comes with lots of nice amenities to make your stay comfortable, including a firepit and a spa tub. Consider Elk River Cabin - 13 Acres, Water Views too. Another cabin with a hot tub near Chestertown, you’ll also have use of a spa tub and a king bed here.
What are the best cabins with pools near Chestertown?
Staying in a cabin rental with a pool adds an extra level of fun to your vacation. If you’d like one near Chestertown, Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay has useful amenities like a swimming pool and a tennis court to make your poolside escape even more unforgettable. Cabin - Maryland Vacation Rental With Private Dock And Pool is another favorite with travelers and features a firepit and a patio.
What are some great Chestertown cabins?
When you want to spend your vacation in nature but aren’t fond of wrestling with your pop-up tent, a cabin is an excellent choice. Book a few nights at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This traveler favorite comes with nearby museums, a nearby waterfront and more. Alternatively, experience comfort and outdoor fun in the perfect package at August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool. Nearby museums and a swimming pool are among this retreat’s amenities.
What are the best weekend cabin rentals in Chestertown?
If you can’t wait to spend a couple of relaxing days surrounded by nature, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is calling your name. Kick back here for a long weekend and make use of conveniences including a barbecue grill and a patio. Another impressive retreat is August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool. Offering a swimming pool, a firepit and plenty of peace and quiet, you’ll go home feeling all brand new.
What are the best cabin prices in Chestertown?
If you’d love to save a few pennies on your stay, we’ve got some terrific deals on Chestertown cabins that won’t put a hole in your wallet. Like the sound of $315 per night?This price was 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.
Can I find log cabins in Chestertown?
If you’re looking for a more relaxed pace of life, you’ll find it at one of our log cabins in Chestertown. For instance, 1850 Historic Log Cabin. Spend your days here surfing and hiking and then return home to its rustic charms. Time also appears to go slow at Log Cabin In Townsend Delaware. When you’re ready to venture beyond your front step, stand-up paddle boarding and bird watching opportunities are close by.
What are the highest-rated cabins in Chestertown?
With an impressive rating, it’s easy to see why Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a hit with vacationers. It offers useful amenities like a barbecue grill and a patio. August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool is another excellent choice. Conveniences like a swimming pool and a firepit will help make your stay nice and comfy.
What are the top things to see and do in Chestertown?
Any good cabin escape should include checking out the local sights. For example, Washington College. It’s among the best attractions around Chestertown. If you’d like to journey farther out, grab a rental car and make tracks to Rolphs Wharf Marina.
Why should I book a cabin in Chestertown?
Affordability, nature-filled surroundings, rustic charm — there are loads of good reasons to stay in a Chestertown cabin. Leave behind the noise of the city and rise with the sound of songbirds and wildlife. There’s a whole lot of adventure just outside your door too. Whether you’re taking a break with family, friends or your partner, you’ll discover the perfect cabin on Expedia.
What are the top nature cabins in Chestertown?
If you can bear to step away from the home comforts of Cabin - Vintage Waterfront A Frame - Hideaway On The Bay, adventure awaits. Among the best nature cabins in Chestertown, it offers easy access to the great outdoors and amenities such as a nearby beach and on-site watersports. Cabin - - Picturesque Wooded Property With Unique Tiny House should also be on your list. Location, a firepit, on-site watersports … They’re just a few things to love about this place.

Recent reviews of Chestertown hotels
Expedia verified reviews

Holiday Inn Express White Marsh, An IHG Hotel

Holiday Inn Express White Marsh, An IHG Hotel

5/5 Excellent
"Always clean "
A verified traveler stayed at Holiday Inn Express White Marsh, An IHG Hotel
Posted 2 days ago
Holiday Inn Express White Marsh, An IHG Hotel