Vacation rentals with a patio in Chesapeake City

Find and book unique patio rentals on Airbnb

Quick stats about vacation rentals with a patio in Chesapeake City

  • Total vacation rentals

    Explore 10 vacation rentals in Chesapeake City

  • Nightly prices starting at

    Chesapeake City vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

  • Verified guest reviews

    Over 1,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Chesapeake City vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake City rentals

  • 4.9 Average rating

    Chesapeake City stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated patio rentals in Chesapeake City

Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Home in Chestertown
4.98 out of 5 average rating, 181 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.

Top guest favorite
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.
Apartment in Chestertown
5 out of 5 average rating, 148 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!

Top guest favorite
The lighthouse replica is shown from an elevated angle, surrounded by trees and located beside the water. A wrap-around deck is visible, along with the charming architectural details of the structure and the contrasting red roof.
Home in North East
4.96 out of 5 average rating, 132 reviews

Red Point Lighthouse

Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

Top guest favorite
A charming two-story red brick home features large windows with black shutters, allowing ample natural light to enter. Lush green landscaping surrounds the entrance, which includes a white front door flanked by elegant outdoor sconces. The overall impression reflects a well-maintained historic residence.
Home in North East
4.94 out of 5 average rating, 138 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.

Top guest favorite
The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.
Place to stay in Airville
4.98 out of 5 average rating, 275 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Guest favorite
Guesthouse in Elk Mills
4.97 out of 5 average rating, 165 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Top guest favorite
A wooden deck is presented with two rocking chairs, positioned on a textured area rug. Surrounding trees offer a lush backdrop, enhancing the natural setting. The rustic log construction of the cabin complements the peaceful ambiance of the outdoor space.
Cabin in Cecil County
5 out of 5 average rating, 124 reviews

Waterfront cabin home - 9+ private wooded acres

Gunpowder Cabin is a peaceful getaway set on 9+ wooded acres and a private drive in Northern Maryland, just an hour from Baltimore. With a half mile of hiking trails, and over 600 feet of frontage on Octoraro Creek, there are numerous options for taking in the natural beauty: warm up by our two firepits, lounge in a hammock, take a dip in the river, or fish for trout from the shoreline. A secluded retreat that feels remote, but moments from the civilization you came to escape.

Top guest favorite
A spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.
Guest suite in Peach Bottom
5 out of 5 average rating, 203 reviews

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

Top guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 282 reviews

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Top guest favorite
Cabin in Airville
4.98 out of 5 average rating, 164 reviews

Romantic. Waterview. Hot Tub. 1 hour to Baltimore.

Welcome to our secluded, modern creekside cabin for the ultimate relaxing vacation. Escape to this luxury retreat in Airville, PA perfectly located for guests from NYC, Philadelphia & Baltimore. Unwind in the private hot tub, gather around the fire pit, and enjoy peaceful creek views. Featuring 3 queen beds, luxury linens, and spa-style amenities, this cozy, private cabin offers boutique comfort, ideal for romantic getaways or relaxing nature retreats.

Top guest favorite
The living area includes comfortable seating with a brown leather couch and two armchairs, one of which is a reclining style. A coffee table sits at the center, adorned with a bowl of fruit. Natural light enters through the windows, which are partially covered by blinds.
Apartment in Elkton
4.91 out of 5 average rating, 149 reviews

477 Lovely 2 bedroom unit with free parking

475 is a Lovely 2 bedroom unit with free parking. If the unit is booked for the dates you wanted please use the link below to check unit 477 which is its mirror image right next to it. The dates that you wanted to book may be available. Use this link: https://www.airbnb.com/rooms/1513941590144353519?source_impression_id=p3_1765561312_P3YnBwuhD-njvDvn Just copy and paste the above link. If you are using an IOS device the link must be entered manually.

Top guest favorite
Cottage in Havre de Grace
4.99 out of 5 average rating, 104 reviews

Chapel Cottage |Hot Tub |Pet Friendly |Near Ripken

Welcome to our cozy hideaway nestled in the heart of Havre de Grace, Maryland. Whether you’re seeking relaxation or adventure, our thoughtfully designed cottage offers comfort, convenience, and a touch of whimsy. Enjoy your own fire pit in the private pet friendly fenced in yard. 6 person hot tub, towel warmer and cold plunge in the She Shed. We are 3.5 miles from downtown (waterfront) Havre de Grace, and less than 5 miles from Ripken Stadium.

Popular amenities for Chesapeake City patio rentals