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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 30 Apartments in Kennedyville with updated reviews, rates, and availability.

Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (23)
"Wonderful spot in the center of historical Chestertown,"
Newly restored apartment in the heart of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (29)
"The cottage was comfortable and welcoming. It was close to restaurants, the Farmers' Market and delightful shops and galleries."
Historic Downtown Garden Oasis with Private Patio
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Aerial view

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

The price is AED 595
AED 810 total
includes taxes & fees
20 May - 21 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (83)
"Quiet neighborhood and the best place to stay."
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown
Private 3 room Queen Suite w/Kitchenette
Exterior

Private 3 room Queen Suite w/Kitchenette

10.0 out of 10, Exceptional, (25)
"Perfect location for that town. "
The price is AED 459
AED 783 total
includes taxes & fees
6 May - 7 May
Private 3 room Queen Suite w/Kitchenette
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (35)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (17)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is AED 826
AED 1,367 total
includes taxes & fees
6 May - 7 May
Waterfront Retreat with Private Dock and Beach
Country Get Away 1 Bedroom Apartment
Property grounds

Country Get Away 1 Bedroom Apartment

9.8 out of 10, Exceptional, (31)
"Easy check in, peaceful setting, clean & close to Chesapeake City"
The price is AED 257
AED 409 total
includes taxes & fees
12 May - 13 May
Country Get Away 1 Bedroom Apartment
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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

10.0 out of 10, Exceptional, (10)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is AED 250
AED 459 total
includes taxes & fees
12 May - 13 May
Guest Suite for up to 2 in a Victorian on the Chester River
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Miscellaneous

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

10.0 out of 10, Exceptional, (5)
"Perfection"
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL, WATER TOY PARKING, WALK TO TOWN
Property grounds

CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL, WATER TOY PARKING, WALK TO TOWN

10.0 out of 10, Exceptional, (7)
"We stayed 4 nights and it was the perfect place! Plenty of space, nicely decorated, lovely view of the canal, and very close to all that Chesapeake City has to offer. Wonderfully clean and the manager couldn’t have been more welcoming and helpful! We hope to stay again next year! Thank you!"
CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL, WATER TOY PARKING, WALK TO TOWN
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

2.0 star property
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.6 out of 10, Exceptional, (5)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Historic & Quaint Room downtown Middletown, DE awaits you!
Interior

Historic & Quaint Room downtown Middletown, DE awaits you!

4.0 out of 10, (1)
"1. The room was not like the picture. 2. It is basically a small motel with um, unusual guests and a shared bathroom. 3. The air conditioner would not turn on properly. 4. The owner was communicative and nice, so that was a positive. "
Historic & Quaint Room downtown Middletown, DE awaits you!
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

10.0 out of 10, Exceptional, (2)
"Spent the weekend here. Great location close to everything. Bikes were provided and you can ride to anything in Rock Hall. We would definitely rent here again."
Knot's Landing, spacious Apt. downtown Rock Hall
Discounted Stays | 1BR | Dog-Friendly | King | A/C
Fridge, microwave, oven, stovetop

Discounted Stays | 1BR | Dog-Friendly | King | A/C

10.0 out of 10, Exceptional, (1)
"I rented this property so that I could be near my kids over the holidays. It was a great little place to spend my time. The landlord lives on the property and was very friendly and easy to contact if I had questions. Altogether an excellent experience."
Discounted Stays | 1BR | Dog-Friendly | King | A/C
Beautiful Studio Bedroom Rental!
Interior

Beautiful Studio Bedroom Rental!

Beautiful Studio Bedroom Rental!
The "Dock House"
Outdoor dining

The "Dock House"

10.0 out of 10, Exceptional, (3)
"We couldn't have been happier with our stay. Gary and Diane were wonderful hosts, as well as their dog Lucy! They couldn't have been nicer and more accommodating, so we' are looking forward to booking another stay in the future!"
The "Dock House"
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
The Sunny Place Apt. 1/Bed F/B W/D full kitchen sunroom deck
Marina

The Sunny Place Apt. 1/Bed F/B W/D full kitchen sunroom deck

The Sunny Place Apt. 1/Bed F/B W/D full kitchen sunroom deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kennedyville

BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 1,001 total
includes taxes & fees
6 May - 7 May
BAYSIDE BUNGALOW
Chesapeake Romantic Waterfront Home with Private Pool
Interior

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's it like to stay at an apartment in Kennedyville?
You might have as many choices centrally in Kennedyville, but Expedia can help you locate accommodations within the larger area similar to apartments. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also search for similar properties such as vacation homes, condos, or guest houses.
How do you know if an apartment is a good option for you?
Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in at night and plan out their next day.
What's the best apartment I should consider for a stay in Kennedyville?
Listed below are some of the more popular apartments in the area to choose from: WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Situated in Earleville, 9.4 mi/15.1 km from the heart of Kennedyville. Includes free WiFi and Smart TVs. First Floor Studio Apartment in Historic Chestertown: Located 9.3 mi/14.9 km away in Chestertown. A private pool, laundry facilities, and free WiFi are included. A fitness center and onsite laundry facilities are on site. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace: Located in Havre De Grace, 17.1 mi/27.5 km away. Includes free WiFi. Access to onsite laundry facilities is available on site. Private 3 room Queen Suite w/Kitchenette: Located 21.7 mi/34.9 km away in Port Deposit. Free WiFi, private balconies, and fireplaces are included. Access to onsite laundry facilities is available on site. Waterfront Retreat with Private Dock and Beach: It’s located in Worton, 6.6 mi/10.7 km from Kennedyville. Includes free WiFi, sofa beds, and Smart TVs.
What will the weather be like in Kennedyville?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Kennedyville. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Kennedyville is 48 inches.
What should I see in Kennedyville?
Turner Creek Landing Park and Turner’s Creek 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 the best way to get to and around Kennedyville?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 22.8 mi (36.8 km) from the heart of the city. If you’d like to venture out around the area, you may want a rental car for your journey.