Kennedyville Vacation Rentals from $159: Search Short-Term Rentals

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Our top choices for Kennedyville vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

$144 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

Millington

Riley B.

$118 nightly

Sep 9 - Sep 10

Total with taxes and fees

3. 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.

$183 nightly

Aug 31 - Sep 1

Total with taxes and fees

4. Turtle Cove Room

Kent County

$160 nightly

Aug 31 - Sep 1

Total with taxes and fees

5. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

$272 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Waterfront Retreat with Private Dock and Beach

Worton

Jennifer W.

$343 nightly

Aug 30 - Aug 31

Total with taxes and fees

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

$273 nightly

Sep 8 - Sep 9

Total with taxes and fees

8. Historic Chesapeake City Stay

Chesapeake City

Martha J.

$267 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Kennedyville Hotel Reviews

Great Wolf Lodge Perryville

10/10 Excellent

"A great variety of water slides for the kids to enjoy. The restaurant and hotel accommodations are also nice. My 2 granddaughters had a lot of fun."

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent

"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."

Find out more about Kennedyville

Everything you need to know about Kennedyville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kennedyville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kennedyville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kennedyville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kennedyville rentals

At Expedia, we put the best Kennedyville vacation 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 vacation.

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 vacation rental in Kennedyville?

Yes, there are vacation rentals close to top local attractions in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

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

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This vacation home rental near Kennedyville is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a 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 vacation rental in Kennedyville like?

Vacation rentals are private properties where you can stay for a long or short time in Kennedyville. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Room 1

Check prices for these dates

Our top choices for Kennedyville vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

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

3. Beachcomber Suite

4. Turtle Cove Room

5. Secluded Cottage in Middle of Chestertown

6. Waterfront Retreat with Private Dock and Beach

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

8. Historic Chesapeake City Stay

9. Country Get Away Studio Apartment

10. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

11. Charming 2-bedroom house in Aberdeen with WiFi and AC

12. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

13. Newly restored apartment in the heart of Chestertown

14. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

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

16. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

17. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

18. Private 3 room Queen Suite w/Kitchenette

19. BAYSIDE BUNGALOW

20. Bohemia Manor Farm

Find vacation rentals that suit your style

Top Kennedyville Hotel Reviews

Great Wolf Lodge Perryville

Candlewood Suites Aberdeen-Bel Air by IHG

Holiday Inn Express & Suites Middletown by IHG

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Americas Best Value Inn Edgewood

Red Roof Inn & Suites Chestertown

Find out more about Kennedyville

Frequently asked questions