Vacation rentals in Kent County

The Blissful Retreat @theblissfulretreat

Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. You'll spot deer, bunnies, frogs, turtles, birds and so much more from the lovely front porch! As a Nurse I can guarantee our space has always been cleaned and sanitized to the highest standards, regular use of a ozone light. Check us out on insta for more blissfulness - theblissfulretreat and FB- theblissfulretreatrockhall

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Heart of Historic Chestertown - Church Alley

This beautifully restored townhouse blends colonial charm with modern comforts, plus the added convenience of its unbeatable location. On a quiet block in the heart of historic downtown, all the local staples are just steps from your door-- the farmers market, beloved festivals, fine dining and the scenic Chester River! Enjoy cooking in the fully outfitted kitchen, dining al fresco on the patio, and entertaining your company with two stylish and distinct living spaces on the first floor.

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Owl Cottage - Cozy, Private & Walkable to Town

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown. It has a 1st floor bedroom with king bed, a light-filled 2nd floor living room and kitchenette, and a third story loft, with a queen size bed. There is also a bathroom with shower on the second floor. Beds furnished with luxury linens. There is a private patio with chairs and access to over 2 acres of private gardens.

Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

2 Beds, 2.5 Baths - Perfect Downtown Location

Charming and inviting, this beautifully updated home in historic Chestertown offers the perfect blend of comfort and location. Featuring 2 bedrooms—each with its own en suite bath—plus an additional half bath on the first floor, it comfortably accommodates up to 4 adults. Enjoy bright, thoughtfully designed living spaces throughout. Just a few blocks from downtown shops, restaurants, and waterfront, and an easy walk to Washington College.

Carriage House Studio -Secluded "Treehouse" Escape

Escape to a hidden sanctuary in Chestertown. Perched on the 2nd floor of a historic building, this private 800 sq ft carriage house feels like a luxury treehouse with canopy views, fully screened from the outside world. Perfect for a romantic getaway or solo retreat, it blends total privacy with town-center access. Enjoy a fireplace, premium linens, off-street parking, and full access to over an acre of breathtaking private gardens.