Holiday rentals in Kennedyville

4.95 out of 5 average rating, 141 reviews

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.

Guest suite in Joppatowne

4.99 out of 5 average rating, 153 reviews

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

Guest suite in Chestertown

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)

Guest suite in Chestertown

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.

4.82 out of 5 average rating, 72 reviews

Cottage in Betterton

Cottage By the Chesapeake

This cozy cottage on the Eastern Shore of Maryland sits on a spacious private lot a five minute walk to Betterton Beach! Relax on the screened-in porch or fully-furnished living room after a day at the beach, or cook a homemade dinner in our fully-equipped kitchen. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH! For a change of pace or a night out, Chestertown, Maryland is only a short drive away.

4.97 out of 5 average rating, 129 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

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

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.

4.95 out of 5 average rating, 73 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

4.97 out of 5 average rating, 236 reviews

Flat 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.

Serviced apartment in Chestertown

5 out of 5 average rating, 111 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!

Superhost

5 out of 5 average rating, 4 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

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Popular amenities for Kennedyville holiday rentals

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Other great holiday rentals in Kennedyville

4.94 out of 5 average rating, 69 reviews

Beautifully remodeled home in Historic Chestertown

SharonRating, 5 stars3 weeks ago

This was a lovely place to stay on the eastern shore of Maryland. The house was clean and a perfect place to stay the night before our triathlon.

5 out of 5 average rating, 14 reviews

High Tide & Hound

KellyRating, 5 stars1 day ago

Jessica's place was perfect. Our dog loved hanging in the back yard and walking the trail. Lots of fun places within walking distance. The box of treats from a nearby bakery that were waitin for us when we arrived were a great unexpected touch. Highly recommend!

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.

Guest house in Chestertown

5 out of 5 average rating, 31 reviews

Owl Cottage - Cozy, Private & Walkable to Town

ElizabethRating, 5 starstoday

Lovely cottage, exactly as described. Bedding was very comfortable. Thoughtful little touches like creamer for coffee and snacks were much appreciated.

5 out of 5 average rating, 44 reviews

Home in Betterton

Ruby's Sea Glass Cottage near Betterton Beach

NaomiRating, 5 stars1 week ago

This was such a peaceful and beautiful getaway. The house was so charming and immaculate. That goes for interior and the exterior. We celebrated Father’s Day weekend here and our husbands had a blast fishing the pier and our littles walking to the beach. The rain head shower head and the heated bathroom floor was to die for, and enjoying a book on all the wonderful porches and beautifully kept backyard! We hope to visit again soon! Thank you so much.

Guest suite in Chestertown

4.96 out of 5 average rating, 73 reviews

Historic Downtown Garden Oasis with Private Patio

TimothyRating, 5 stars1 week ago

The space was perfect for a weekend getaway for two. It was cozy, well decorated and and very clean. It is a really short walk to downtown but very quiet on the patio. Everything matched the photo's and description, so it was exactly what we were expecting. We didn't get to take advantage of all that downtown has to offer and will definitely be back again.

Superhost

Apartment in Betterton

4.92 out of 5 average rating, 38 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

SihamRating, 5 stars2 weeks ago

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!