Holiday rentals with a patio in Chestertown

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Top-rated Holiday Accommodation with Outdoor Verandahs in Chestertown

Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.

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Guest favourite

Home in Shady Side

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!

Guest favourite

Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Guest favourite

Home in Chestertown

123 High-Fully renovated Historic Brick Victorian

Luxurious Brick Victorian - Beautiful, fully restored brick Victorian, built in 1870, central to downtown. The house went through a 14-month total renovation with close attention to details. Lots of light and exposed brick walls. Stunning brick garden walk w/outdoor private patio. Walking distance to downtown shops, restaurants & parks. Just a short walk to the wonderful Chester River. Chestertown is known for its historic significance as well as its various festivals throughout the year.

Guest favourite

Home in Chestertown

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.

Guest favourite

Casa particular in Chestertown

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!

Guest favourite

Barn in Chestertown

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.

Guest favourite

Serviced 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!

Guest favourite

Home in Chestertown

Magnolia House: walk to shops, restaurants, river

Historic details abound in this 1750s colonial gem surrounded by inviting gardens and located in the heart of historic Chestertown. 2 blocks from the scenic Chester River, and just steps away from High Street's (aka Chestertown's "Main Street") Saturday Farmer's Market, bakery, historic soda fountain, shopping, art galleries, dining, and downtown community events. As described by the New York Times: "This house is one of the contributing buildings in the town's historic district..."

Guest favourite

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Pool opens Memorial Day weekend! 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.

Guest favourite

Home in Chestertown

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.

Guest favourite

Guest suite in Bel Air

Bel Air SleepEasy

Keep it simple at this peaceful and centrally-located place (near Upper Chesapeake Hospital and historic downtown Bel Air). Lovely Bedroom with private bathroom and shower. Private entrance into your sitting room and “kitchenette” area (not a full cooking kitchen). Keurig coffee and drip coffee pot, mini frig, microwave, toaster oven, cups, plates, utensils. The room and patio are non-smoking environments. No smokers please.

Guest favourite

Guesthouse in Glen Burnie

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