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 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

ﺩ.ﺇ829 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 14 – 21

ﺩ.ﺇ507 per night

Guest favorite

Barn in Chestertown

4.96 out of 5 average rating, 26 reviews

Pet friendly romantic hideaway in center of town.

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of C’town. 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’s a private patio with chairs and Solo stove plus access to over 2 acres of private gardens.

Jul 6 – 13

ﺩ.ﺇ711 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 25 – Aug 1

ﺩ.ﺇ617 per night

Guest favorite

Guesthouse in Towson

4.99 out of 5 average rating, 176 reviews

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Dec 2 – 9

ﺩ.ﺇ528 per night

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 118 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Jul 15 – 22

ﺩ.ﺇ657 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 14 – 21

ﺩ.ﺇ690 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

Oct 16 – 23

ﺩ.ﺇ854 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.

Aug 5 – 12

ﺩ.ﺇ855 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.

Jun 26 – Jul 3

ﺩ.ﺇ1,498 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!

Oct 6 – 13

ﺩ.ﺇ620 per night

Superhost

Cabin in Goldsboro

4.88 out of 5 average rating, 104 reviews

Wigwam Lodge~Hot Tub~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...

Jun 25 – Jul 2

ﺩ.ﺇ813 per night