Vacation rentals with a patio in Chestertown

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Top-rated patio rentals in Chestertown

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Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 117 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Dec 26 – Jan 2

R10,182 ZAR per night

Guest favorite

Home in Chestertown

4.96 out of 5 average rating, 73 reviews

Cozy 3-bedroom home w/ screened in porch & 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.

Dec 5 – 12

R4,190 ZAR per night

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 103 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!

Dec 19 – 26

R2,562 ZAR per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 69 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!

Jul 24 – 31

R3,120 ZAR per night

Guest favorite

Townhouse in Baltimore

4.96 out of 5 average rating, 113 reviews

Loaded Home - Heart Of Fells Point Waterfront Area

Literally located steps away from the waterfront in Historic Fells Point, Baltimore City, Maryland. Walking distance to all that Fells Point has to offer - to include restaurants, shops, stores, bars, family gathering areas, and water taxis to other desired waterfront locations in Baltimore City. Home is fully loaded & has a rooftop desk with a wonderful view of the Fells Point Waterfront, state-of-the-art appliances, TVs in multiple rooms, incredible ambiance, and great comfort.

Dec 31 – Jan 7

R2,871 ZAR per night

Guest favorite

Home in Chestertown

4.89 out of 5 average rating, 27 reviews

Beautifully remodeled home in Historic Chestertown

Discover Chestertown and stay in this charming, newly renovated 2 bd/1.5 bath family friendly house (part of Historic District). Can sleep 5 (2 queen beds, 1 twin). 4 min walk to the fountain park and the restaurants (Watershed, the Kitchen, Bad Alfred's, etc). 2 min drive/6min walk to Washington College. -No smoking (any kind) in the house. -No parties/gatherings. -Please no shoes in the bedrooms as they are carpeted. -Be aware of steep stairs.

Jul 27 – Aug 3

R3,488 ZAR per night

Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 263 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Nov 29 – Dec 6

R4,427 ZAR per night

Guest favorite

Guest suite in Arnold

4.97 out of 5 average rating, 129 reviews

Pet Friendly Captains Quarters, Near Annapolis, EV

Yes, the hot tub IS open! 24/7/365 :-) This space has been fully updated with all the conveniences and amenities to make your stay enjoyable! We offer: - a king bed so you get a stellar night's sleep, - a queen bed sleeper sofa for family travels, - high speed internet, - a furnished kitchen, - private en-suite bathroom, and - a coffee bar. We're close to everything - located four miles from my hometown Annapolis!

Aug 17 – 24

R3,666 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

NEW Chestertown Retreat

Enjoy this brand new semi-detached home (construction completed in July 2023) with new furnishings and fully stocked with everything you need. 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, or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

Sep 1 – 8

R4,321 ZAR per night

Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

Jan 1 – 8

R2,716 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Oct 15 – 22

R7,492 ZAR per night

Guest favorite

Guest suite in Chestertown

4.94 out of 5 average rating, 48 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!

Nov 16 – 23

R3,230 ZAR per night