Vacation rentals with outdoor seating in Kent County

4.95 out of 5 average rating, 141 reviews

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

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.

Superhost

The charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.

Cottage in Rock Hall

4.88 out of 5 average rating, 128 reviews

Cottage with Modern Updates - Walk to Waterfront!

Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

Guest suite in Chestertown

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

4.99 out of 5 average rating, 225 reviews

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.

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

4.97 out of 5 average rating, 129 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

A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.

4.92 out of 5 average rating, 148 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!

The image displays a serene riverside view at dusk, featuring calm waters reflecting shades of pink and purple clouds. A wooden dock extends into the water, flanked by lush greenery and subtle seating areas, offering a tranquil atmosphere for relaxation.

5 out of 5 average rating, 19 reviews

Holiday Escape to the Riverside

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

A hot tub bubbles gently in the foreground, surrounded by lush greenery and a view of the waterfront. Twinkling string lights hang above the screened porch, which features a spacious dining area. The sunset casts a warm glow over the scenic landscape.

4.95 out of 5 average rating, 73 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

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

A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.

4.97 out of 5 average rating, 236 reviews

Private cozy cottage - center of Chestertown .

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.

5 out of 5 average rating, 111 reviews

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!

Superhost

An open-concept living area is featured, incorporating a kitchen with a large marble island and dark-stained seating. A wooden dining table is positioned nearby, while a comfortable seating area is arranged around a stone fireplace, illuminated by natural light from surrounding windows.

5 out of 5 average rating, 4 reviews

Relaxing Waterfront - Golf Course & Sunset Views

Our home away from home in Chestertown is truly an extraordinary property. Water and golf course views from every room. And wildlife! Some of the birds and animals we've seen: - blue herons - bald eagles - ospreys - ducks - turtles - otters Inside, there's room enough for 8, with 3 bedrooms and 3 full bathrooms, including one of each on the main level. Just one mile from downtown Chestertown, and a short walk to Chester River Yacht & Country Club

A cozy living area features a mustard yellow sofa complemented by two light gray armchairs. A round coffee table with a decorative tray sits on a soft area rug. Neat window blinds provide controlled natural light, enhancing the room's inviting layout.

4.98 out of 5 average rating, 45 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.

Adirondack chairs are arranged around a fire pit on a grassy riverside. A vibrant sunset casts pink and orange hues across the sky and reflects on the calm water, creating a serene outdoor atmosphere. A tree stands nearby, adding to the peaceful setting.

5 out of 5 average rating, 40 reviews

Down by the River

Relax while taking in the beautiful river views in this bright and welcoming home. Walk to town to enjoy all the delights of charming historic Chestertown. Kayak on the river, unwind on the dock, cook a gourmet meal in the huge open kitchen, relax by the fire-pit. This fully updated, light, and open home is a calming oasis and welcoming gathering place for family and friends. Fully accessible as well.

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Popular amenities for Kent County outdoor seating rentals

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Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 90 reviews

River front cottage with private dock & water fun

MatthewRating, 5 stars3 weeks ago

The home was lovely, right on the river, and felt....homey. It was the kind of place I would have if I had a home on the river. There were friendly neighbors who gave us some advice on what to do/not to do in the area and we had a lovely time. This might just be an annual trip for me and my extended family.

A wooden pier extends from the sandy shore towards a home surrounded by tall trees, with warm light glowing from large windows. The sky displays soft pink and blue hues as the day transitions to evening.

4.93 out of 5 average rating, 45 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

MaxRating, 5 stars3 weeks ago

This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!

A cozy living area features warm wood paneling and a rustic ceiling. A spacious sectional sofa is arranged around a wooden coffee table on top of an area rug. A dining table for four is positioned nearby, with natural light coming through the windows.

4.93 out of 5 average rating, 30 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.

4.94 out of 5 average rating, 31 reviews

An expansive deck with a wooden dining table is surrounded by several chairs. Lush greenery provides a natural backdrop, and a winding path leads down toward the waterfront, offering a view of the serene Chester River.

Home in Millington

Lark's Nest on the Chester River

MichaelRating, 5 stars5 months ago

Amazing best describes our stay. Planning on coming back every year if they will have us. We stay in a lot of places, but this was absolutely amazing. Cant wait to book for next December

4.89 out of 5 average rating, 36 reviews

A spacious bedroom is illuminated by natural light from a window with light-colored blinds. A large bed with a dark headboard is centered in the room, accompanied by two pillows. Nearby, a floor lamp and a decorative curtain add soft accents to the neutral-toned walls.

Home in Rock Hall

The Blue Jimmy

AmandaRating, 5 stars1 month ago

We stayed for the weekend when our son had a baseball tournament. One of teammates came with us and this was perfect for everyone to have their own room and space to spread out. The house was neat and clean and we felt right at home this weekend. Would definitely consider staying here again if we’re ever back in the area.

A well-appointed bedroom features a spacious bed dressed in blue linens, complemented by decorative pillows. A cozy throw rests at the foot of the bed. A mounted artwork depicting a ship on the water is visible above the headboard, and soft lighting is provided by a bedside lamp.

5 out of 5 average rating, 78 reviews

Lovely Home in Chestertown With Free EV Charging

SheridanRating, 5 stars1 week ago

Perfect place for our during a nearby wedding. Teddi was always responsive, pleasant, and helpful.

A bright sunroom features large windows that allow natural light to fill the space. Comfortable seating includes a vibrant pink sofa and two green chairs beside a small accent table. A soft area rug lays on the floor, enhancing the cozy atmosphere.

5 out of 5 average rating, 42 reviews

In Town Chestertown Rancher (1 Block to College)

KatieRating, 5 stars1 week ago

Tim’s house was perfect for our group of 4 adults and 4 kids. It’s very cute, clean, and spacious. His level of hospitality did not go unnoticed, he seemed to of thought of everything. The kitchen was well equipped for cooking if you choose to do that. We would definitely stay here again!

The exterior of the home is framed by lush greenery and a well-maintained lawn. The two-story structure features a gabled roof and a screened-in porch, inviting relaxation in a quiet, residential setting surrounded by trees.

4.96 out of 5 average rating, 25 reviews

Lotus House: porches, decks, yard, beach access

JamesRating, 5 stars4 months ago

House was beautiful, clean and host was phenomenal. Highly recommend!

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Apartment rentals with outdoor seating

4.97 out of 5 average rating, 32 reviews

A private bedroom features a spacious bed adorned with a patterned bedspread. Two bedside lamps provide soft lighting on either side. Light filters through a window with blinds, highlighting the wall's calming shade and the neutral-toned carpet underneath.

Apartment in Rock Hall

Traveler Guest Suite - Cinnamon By The Bay

JoeyRating, 5 stars2 months ago

Deborah was an amazing host, super responsive and incredibly kind. The room was spacious, and we absolutely loved it. Everything was perfect!

5 out of 5 average rating, 16 reviews

Cozy One Bed/One Bath Apartment in Chestertown

CoryRating, 5 stars3 days ago

Caitlin is the best host I've experienced when using airbnb. She was always proactive in reaching out and made us feel at home. She had snacks and drinks available which was very thoughtful. This is the perfect option for staying in the area and walkable to many restaurants. The basement apartment was clean and had everything needed.

4.97 out of 5 average rating, 35 reviews

The queen-sized bed is dressed in soft bedding and accented by two pillows. A dark-wood nightstand and a small side table are positioned beside the bed, while an upholstered bench sits at its foot. Green accent walls and framed botanical prints enhance the serene atmosphere.

Apartment in Worton

Elliott House Historic Home Near Chesapeake Bay

SusanRating, 5 stars1 month ago

the place was great. would have preferred to understand it was two stories and I'd be able to request the first story since I walk with the cane. however it was easy for me to get around. extremely clean and the supplies were plentiful. I would recommend someone staying there

4.94 out of 5 average rating, 18 reviews

The entrance features a bright blue door adorned with a seasonal wreath, flanked by two symmetrical windows. A paved walkway leads to the door, bordered by neatly arranged flower beds filled with pink roses. The overall setting presents a welcoming and well-maintained appearance.

Apartment in Rock Hall

Mermaid's Getaway

LarryRating, 5 stars1 week ago

We really enjoyed Rick's place. Everything was just what we needed. He was accommodating to our needs and quite helpful and friendly. He was prompt in answering our questions and taking care of our needs. It was the quiet and friendly atmosphere we needed. Thanks again!

5 out of 5 average rating, 96 reviews

A cozy studio features a full-size bed with light bedding, complemented by a world map artwork on the wall. A seating area includes a chair and small table. Large windows allow natural light to fill the room, enhancing the welcoming atmosphere.

Apartment in Rock Hall

Inspiration Guest Suite - Cinnamon By The Bay

VernaRating, 5 stars3 weeks ago

Fantastic stay! Everything was perfect, comfortable bed, great amenities. Do not hesitate to book, I certainly will again!

The bedroom features a Queen-size bed with light bedding, complemented by a bedside table and lamp. A decorative chair and a small window allow natural light to fill the room, while a door provides access to the back porch.

4.9 out of 5 average rating, 80 reviews

1-br apt in downtown Chestertown (Unit 1)

AliciaRating, 5 stars2 months ago

This spot is a very utilitarian unit but perfect for my dog and me. Very easy to walk to town, the bed was very comfortable and it was great having access to the backyard.

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Condo rentals with outdoor seating

5 out of 5 average rating, 24 reviews

A modern kitchen space is highlighted by stainless steel appliances and wooden accents. Two dining chairs are positioned around a wooden table beside a window, providing a view of the exterior. A patterned rug adds warmth to the wooden floor.

Condo in Chestertown

Historic Loft w/ Park View & Spa Access

AndreiaRating, 5 stars1 week ago

Wonderful stay in Chestertown! Hosts go out of their way to may the experience pleasurable. Would 100% stay here again!

5 out of 5 average rating, 19 reviews

An outdoor covered deck offers seating with a sectional sofa and a coffee table. High chairs are positioned at a bar-style table, with views of greenery and the bay in the distance. The area is brightened by natural light and features a welcoming atmosphere.

Condo in Betterton

Beach Haven Hideout

MarkRating, 5 stars3 days ago

We had a fantastic getaway at Michele's place! The area offers plenty to do - we enjoyed a scenic boat ride and a delicious crab feast. Check-in and check-out were smooth, and Michele was incredibly friendly and helpful throughout our stay. Highly recommended!

Superhost

A sandy beach stretches along the shoreline, dotted with parasols and beachgoers. Calm waters reflect a clear sky, while a pier juts out in the distance, framed by lush greenery. The serene landscape offers a tranquil view of the surrounding nature.

Condo in Betterton

4.92 out of 5 average rating, 38 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

SihamRating, 5 stars2 weeks ago

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!