Vacation rentals in Worton

4.95 out of 5 average rating, 141 reviews

An open staircase with wooden steps leads to a second-floor catwalk, surrounded by large windows offering views of the outdoors. Natural light fills the space, illuminating the warm wood tones of the staircase and the nearby lush greenery visible through the glass.

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.

A historic two-story house is nestled among lush greenery, featuring a muted grey exterior with bright red shutters. The inviting front porch is framed by trees, contributing to the home's serene and picturesque setting.

4.99 out of 5 average rating, 96 reviews

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

An enclosed screened porch is illuminated with soft, warm lighting, creating a welcoming atmosphere. Multiple windows offer expansive views, while a seating area is visible inside. Stairs lead up to the porch, surrounded by lush greenery and brick accents.

4.98 out of 5 average rating, 165 reviews

Chestertown - Eastern Shore Getaway

This century-old three-story home is in the beautiful historic district of Chestertown on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. (NOTE - Airbnb adjusts our rate according to the current demand for rooms)

Two comfortable adirondack chairs are positioned on a wooden deck, facing a scenic view of a tidal creek surrounded by trees. A small black table sits between the chairs, offering a space for refreshments while enjoying the natural surroundings.

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.

4.97 out of 5 average rating, 128 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

An inground pool is surrounded by brick paving, with several lounge chairs positioned nearby. The pool's turquoise water is partially shaded by a large tree, providing a serene outdoor setting. Lush green grass and a wrought-iron fence are visible in the background.

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!

4.93 out of 5 average rating, 58 reviews

A sandy pathway leads through the beach, flanked by patches of grass and sparse trees. The horizon features an expansive view of the water under a clear blue sky, with small groups of visitors scattered along the shoreline, enjoying the sun.

Home in Kennedyville

Comfy and Cozy on the Eastern Shore

Tucked in a quiet, family oriented neighborhood on Maryland's Eastern Shore, this is perfect for a weekend get away or a hunting trip. Bright, cheery bedrooms and a well equipped kitchen. 7 miles from Chestertown will have you enjoying the unique shops, restaurants, and waterfront. Relax on the patio after grilling out. By booking, you agree to follow all rules. Home is not appropriate for children under 8. Guest assumes responsibility for any and all injuries children may experience.

4.97 out of 5 average rating, 236 reviews

A wooden bridge crosses over a lush green landscape, leading towards a two-story building nestled among trees. The property is surrounded by vibrant greenery and features a variety of foliage, creating a serene outdoor environment.

Apartment in Chestertown

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.

5 out of 5 average rating, 110 reviews

A private rooftop deck is presented with a round table and two ornate chairs, surrounded by potted plants. The view features abundant trees and the river in the background, creating a serene outdoor space.

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!

Guesthouse in Chestertown

A doorway leads to a small balcony, framed by ornate wrought iron railings. Bright yellow foliage is visible outside, contrasting with the interior's warm wooden floor and an area rug. Framed artworks adorn the wall beside the door, enhancing the inviting atmosphere.

5 out of 5 average rating, 30 reviews

Owl Cottage - Cozy, Private & Walkable to Town

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

Superhost

5 out of 5 average rating, 3 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

4.99 out of 5 average rating, 71 reviews

A warm sleeping area features a spacious bed made with a textured blanket. A rustic brick fireplace serves as a focal point. Large windows frame the view, providing natural light and enhancing the room's open feel. Vintage decor complements the inviting atmosphere.

Home in Worton

Farm House w/ Water Access (near Chestertown)

The perfect setting for family and friends (up to eight people) to gather and get away to relax. Situated on 140 acres adjacent to Still Pond Creek in Worton, there's room for everyone to spread out -- enjoy the fresh air, outdoor activities and relax in solitude watching abundant wildlife (birds, deer, rabbits, groundhogs, and more!). Chestertown is just 8 miles away with a year round farmer's market, local shopping, art galleries and more.

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Popular amenities for Worton vacation rentals

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Other great vacation rentals in Worton

A screened porch features a comfortable green and white striped chair paired with a small side table. A yellow cushion adds a touch of color. A lantern sits on the table, and a welcoming sign for tourists hangs above, enhancing the inviting atmosphere.

Home in Betterton

5 out of 5 average rating, 5 reviews

Grandma’s Cottage

EricRating, 5 stars2 weeks ago

Kathy’s place is cute and charming and a great location. She’s decorated it thoughtfully (don’t miss the historic postcards!) and it’s been updated with all the modern conveniences; efficient a/c in every room and wi-fi. The screened-in porch is very nice. Her spot is a five-minute walk to the beach and on a quiet street. Kathy was also incredibly nice and thoughtful. We look forward to staying at her place again.

4.97 out of 5 average rating, 89 reviews

River front cottage with private dock & water fun

MatthewRating, 5 stars2 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 bright living and dining area features a long wooden table set with simple decor. Comfortable blue chairs surround the table, while soft seating is arranged nearby. Large glass doors provide an unobstructed view of the water, allowing natural light to fill the space.

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 serene view of the Chesapeake Bay at sunset showcases vibrant hues reflecting on the water's surface. The spacious lawn extends towards the horizon, with a distant bench inviting relaxation. The home's exterior features large windows, highlighting the attractive coastal setting.

Home in Rock Hall

5 out of 5 average rating, 4 reviews

Chesapeake Bay Retreat W/Breathtaking Views

MichelleRating, 5 stars1 month ago

We had an amazing stay! The house was beautiful, clean, and super comfortable and the views were absolutely breathtaking. Everything was just as described, if not better. Joeanna was a great host and made everything easy. We’d definitely love to come back

A welcoming front porch is featured, with a vintage-style bench resting against the wall. Windows adorned with shuttered frames allow natural light to flow in. A potted plant with vibrant flowers adds a touch of color. The porch flooring is finished with a warm red hue.

5 out of 5 average rating, 13 reviews

High Tide & Hound

RickRating, 5 stars1 week ago

One of the cuties places we have stayed. This was a perfect place and set up appropriately for our 3 year old granddaughter and our fur baby. Jessica had also left some snacks which we were so thankful for after the drive. Thanks for a wonderful experience.

4.88 out of 5 average rating, 8 reviews

A serene waterfront view captures a sandy beach with gentle waves lapping at the shore. Lush green trees provide shade along the edge, creating a peaceful and inviting atmosphere. The calm water reflects the clear sky, enhancing the natural beauty of the location.

Apartment in Worton

Waterfront Retreat with Private Dock and Beach

BoRating, 5 stars2 months ago

We really enjoyed the space and the place. There is a clear view down to the water, and we sat on the dock listening to the fish break in the surrounding water, and had a Great Blue Heron fly right by us. We chatted with Kate and Charlie, who obviously love their place, and are happy to share it with others. The appointments in the apartment are beautiful, and it is definitely upscale! We plan on a return trip. Thanks for the stay!

A modern kitchen features white cabinetry and sleek stainless-steel appliances. A window allows natural light to brighten the space, complementing the light-colored tile flooring. A decorative rug lies on the floor, adding a contrasting element to the neutral tones of the kitchen.

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 wooden dining table is set for three, featuring white plates, glasses, and silverware arranged neatly. A decorative tray holds two bottles of wine, with a red circular label visible. The backdrop includes a charming entryway with a subtle pastel-colored wall.