Vacation rentals with a patio in Kent County

4.95 out of 5 average rating, 140 reviews

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

4.94 out of 5 average rating, 93 reviews

Farm stay in Centreville

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

4.93 out of 5 average rating, 30 reviews

Home in Rock Hall

Treehouse

Treehouse is a 3 story duplex townhome with balconies, decks and porch for country relaxation. 3 bedroom 2 full baths and 2 half bath 3 level home. 1 ground floor bedroom with half bath and screened in porch. Main living level on the 2nd floor with Kitchen, dining and living area. 2 small decks on village side and large deck in the trees. 3rd floor features 2 large bedrooms each with full private bathroom. One bedroom has queen bed and one with king bed and small deck overlooking the village.

5 out of 5 average rating, 23 reviews

Condo in Chestertown

Historic Loft w/ Park View & Spa Access

• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in the Chestertown Historic District. • Perfectly positioned to overlook Fountain Park and within walking distance to Washington College and all of downtown Chestertown. • Enjoy unique furnishings that blend early 1900s decor with modern comforts. • Indulge in luxury amenities with priority booking access at Park Row Floats, a renowned exclusive Float Spa located just below.

4.97 out of 5 average rating, 128 reviews

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.

Casa particular in Chestertown

4.92 out of 5 average rating, 147 reviews

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, seasonal hot tub, 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!

5 out of 5 average rating, 25 reviews

Home in Millington

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

5 out of 5 average rating, 109 reviews

Apartment in Chestertown

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!

Guesthouse in Chestertown

5 out of 5 average rating, 28 reviews

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.

4.98 out of 5 average rating, 43 reviews

NEW Chestertown Retreat

Enjoy this newly built (July 2023) semi-detached home with new furnishings, fully stocked with everything you need and private fenced back yard. Located less than 1/2 mile to Washington College and 1.5 miles to downtown, this home is close to everything Chestertown has to offer. Perfect for parents and families visiting students, hunting trips, weddings or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

Guest suite in Chestertown

4.96 out of 5 average rating, 71 reviews

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Superhost

Cabin in Goldsboro

4.85 out of 5 average rating, 147 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

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Popular amenities for Kent County patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

5 out of 5 average rating, 7 reviews

Apartment in Worton

Country Living 3 Bed Historic Cottage Apartment

ShaylynRating, 5 stars6 months ago

It exceeded my expectations based off of the pictures I had saw. Super easy check in and they even left a handwritten card and some snacks for us. Thanks Josiah for the welcoming touch!

5 out of 5 average rating, 13 reviews

Apartment in Rock Hall

DragonflyPeake Studio

KevinRating, 5 stars2 weeks ago

Our stay was terrific. Everything was as described and more. Kimberly thought of Everything. Kimberly was very proactive with advice on things to do and places to go. The place was very clean, updated and comfy. If you are looking for a quiet getaway with great amenities, this is a winner. We definately will be back !

5 out of 5 average rating, 13 reviews

Apartment in Rock Hall

Knot's Landing, spacious Apt. downtown Rock Hall

LaurenRating, 5 stars8 months ago

Our second stay at Matthew’s place was fabulous! So close to everything downtown, easy access, great to be able to bring the dog, so clean and quaint. Can’t wait to go back for another Rock Hall stay!

5 out of 5 average rating, 14 reviews

Apartment in Chestertown

114 High Street First Floor Unit Chestertown

JodyRating, 5 stars1 week ago

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!

4.9 out of 5 average rating, 29 reviews

Apartment in Warwick

Cozy peaceful apartment

JackieRating, 5 stars2 weeks ago

Very clean and quite apartment and Rebecca is very quick in responding me and so generous.

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House rentals with a patio

4.94 out of 5 average rating, 68 reviews

Beautifully remodeled home in Historic Chestertown

JoannaRating, 5 stars1 month ago

It was a very clean and the location is ideal for any downtown activity! The host was very accommodating!

4.97 out of 5 average rating, 34 reviews

Home in Stevensville

Spacious4BR home with waterviews

GaryRating, 5 stars2 weeks ago

5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.

4.97 out of 5 average rating, 29 reviews

River Cottage, Chestertown

FranklinRating, 5 stars8 months ago

Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.

4.93 out of 5 average rating, 30 reviews

Home in Millington

Lark's Nest on the Chester River

LaurelRating, 5 stars5 months ago

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

5 out of 5 average rating, 31 reviews

Home in Rock Hall

1-Particular Harbor: A Coastal Oasis!

FrannieRating, 5 stars2 days ago

We had an amazing weekend and Gregory’s home was perfect. So clean and well equipped. Gregory thought of everything!! Highly recommend ⭐️⭐️⭐️⭐️⭐️

5 out of 5 average rating, 41 reviews

Home in Betterton

Ruby's Sea Glass Cottage near Betterton Beach

KimberlyRating, 5 stars1 week ago

Took my children on a little getaway. We had a great time. House was very cozy and clean. There was lots of stuff provided for guest. Most of which we couldn’t use due to rain. We would definitely like to come back again!

5 out of 5 average rating, 31 reviews

Home in Stevensville

Screened Porch | Near Bay Bridge & USNA | Big Yard

JenRating, 5 stars2 days ago

Karin was very responsive to our last minute booking. The house was as described and directions were clear. We cannot thank the hosts for assisting us during a difficult time.