Photo by Assya A

Search the Best Cabins in Chestertown

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

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

Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is $629
$1,438 total
includes taxes & fees
Jun 5 - Jun 6
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
Accommodation
 Cabin Rentals
Lowest Price
Highest Price

Frequently asked questions

What are the best cabins near Chestertown?
Experience the outdoors without giving up the comforts at one of our 23 cabins in and around Chestertown. Whether you have relaxation or adventure on your to-do list, Cozy Cabin Happiness has plenty of both. Alternatively, spend your vacation at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay and make the most of its pretty 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 to 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 hot tub cabins near Chestertown?
If you’re someone who thinks a hot tub is a must-have while on vacation, you’ll enjoy Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This charmer comes with lots of conveniences designed to make your stay comfortable, including a firepit and a spa tub. Look into Elk River Cabin - 13 Acres, Water Views as well. Another cabin with a hot tub near Chestertown, you’ll also have access to a spa tub and a king bed here.
What are the best cabins with pools near Chestertown?
Put on your swimwear and enjoy a few laps whenever you please when you reserve one of our cabin rentals with a pool. Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay is a standout. A barbecue grill and a tennis court are some other amenities that’ll help make your stay comfortable. Or you can enjoy a break from the hustle and bustle at Cabin - Maryland Vacation Rental With Private Dock And Pool. As well as a refreshing pool, this cabin comes with a firepit and a patio.
What are some great Chestertown cabins?
Nestled in nature but still with the comforts you need, you can’t go past a cabin if you’re looking to truly experience the great outdoors. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is an excellent place to escape from it all. Amenities here include nearby museums and a nearby waterfront. August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool is another sought-after property. Nearby museums and a swimming pool will help make your stay even more comfortable.
What are the best weekend cabin rentals in Chestertown?
Whether you’re organizing a quick trip with your sweetheart or your entire family, we’ll help you locate the ideal weekend cabin getaway. One top example? Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Featuring a barbecue grill and a patio, you’ll adore waking up in nature here. August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool is another place where you can hit pause on life. Spend a few nights at this escape which offers a swimming pool and a firepit.
Can I find log cabins in Chestertown?
For some, the perfect outdoor vacation isn’t complete without bunking down in a charming log cabin. Get exploring or simply switch off and relax at 1850 Historic Log Cabin. Recreational activities such as hiking and rafting are among the exciting things to do here. Another popular log cabin getaway is Log Cabin In Townsend Delaware. Canoeing and stand-up paddle boarding will keep you on the go when you’re not hibernating in your comfy hideaway.
What are the highest-rated cabins in Chestertown?
Travelers keep coming back to Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This superb option comes with a host of useful amenities including a firepit and a patio. It’s not hard to understand why August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool is also a favorite with travelers. Conveniences like a swimming pool and a barbecue grill help make it a winner.
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 have in common — excellent access to the great outdoors. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay lures vacationers in search of adventure. Amenities such as a firepit and a nearby beach add to its appeal. Whether you’d prefer to get your feet moving or just put them up, do it at Cabin - - Picturesque Wooded Property With Unique Tiny House. Another favorite, it offers on-site watersports and a firepit.

Recent reviews of Chestertown hotels
Expedia verified reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
"This is the second time I've stayed here and both experiences were extemely positive. I don't have one bad thing to say!"
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 1 day ago
Fairfield Inn & Suites by Marriott White Marsh