Kennedyville Holiday Rentals from €166: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Kennedyville has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay : This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

Check prices for these dates

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Our top choices for Kennedyville holiday rentals

1. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

7 Sept - 8 Sept

2. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

includes taxes & fees

7 Sept - 8 Sept

3. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

includes taxes & fees

8 Sept - 9 Sept

4. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

includes taxes & fees

4 Oct - 5 Oct

5. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

includes taxes & fees

14 Sept - 15 Sept

Luxury House, Multiple Bedrooms, Lake View

6. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

21 Sept - 22 Sept

7. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

includes taxes & fees

10 Sept - 11 Sept

8. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

7 Sept - 8 Sept

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Top Kennedyville Hotel Reviews

Red Roof Inn & Suites Chestertown

10/10 Excellent

"Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating."

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"Front desk pleasant and helpful, but… no accessible rooms available. Also, only non pet room available (even though reservations were made) was on 2nd floor and elevator out of service. Room itself was clean. Breakfast was good."

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent

"Five-Star Stay! My wife and I had an outstanding stay at La Quinta Inn in Aberdeen, Maryland. The room was absolutely spotless, and the property appeared to have been recently renovated—it felt fresh and almost brand new. When we checked in Friday, September 4, at approximately 8 PM, the young gentleman at the front desk was exceptionally helpful, professional, and welcoming. We were so impressed that we asked his age, and he told us he was 21. Unfortunately, I don’t remember his name, but I hope management can identify him from the date and time and recognize him for his excellent customer service. He represented the hotel extremely well. The next morning at breakfast, we met a wonderful woman who was maintaining the breakfast area. Again, I apologize that I don’t remember her name, but she was incredibly gracious, friendly, and helpful. The breakfast was tasty, and the atmosphere was excellent. I also enjoyed a relaxing swim in the beautiful outdoor pool Friday evening—a perfect way to unwind after traveling. Overall, this was truly a five-star experience. The cleanliness, recent renovations, amenities, and especially the wonderful staff made our stay exceptional. We would definitely stay here again!"

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent

"Katy & Shad was the best when it comes to customer service, check in & check out with them was super great! The housekeeping staff was great and of course a tip was left. The hotel was very clean, and location in the mist of everything. Also the breakfast was great as well. This hotel and it's location is definitely a 5 Star!"

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Find out more about Kennedyville

Everything you need to know about Kennedyville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kennedyville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kennedyville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kennedyville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kennedyville. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kennedyville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kennedyville holiday rentals we have selected for you start as low as €166 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kennedyville rentals

At Expedia, we put the best Kennedyville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kennedyville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kennedyville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kennedyville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Kennedyville?

Yes, there are holiday rentals close to the most popular sights in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kennedyville has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Kennedyville?

Turner's Creek Park and Turner Creek Landing Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Crow Farm and Vineyard and Kent Museum.

What’s a holiday rental in Kennedyville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennedyville. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Kennedyville holiday rentals

1. Newly restored apartment in the heart of Chestertown

2. First Floor Studio Apartment in Historic Chestertown

3. Wren Retweet- Country Estate in Center of C’Town