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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

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, (21)
"We loved this apartment. The communication with the owner was very timely and clear!"
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, (27)
"Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants."
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 806 total
includes taxes & fees
29 Apr - 30 Apr
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, (81)
"Clean, well appointed, plenty of space, all small amenities were thought of. We would definitely come back. Very responsive owner too!"
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)
"Very nice. "
The price is AED 441
AED 759 total
includes taxes & fees
24 Apr - 25 Apr
Private 3 room Queen Suite w/Kitchenette
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets

Carriage House Hideaway in Middle of Chestertown

10.0 out of 10, Exceptional, (87)
"If I could give these hosts 10 stars, I would! They went above and beyond for me! Their kindness and helpfulness was way beyond what I would have expected from a host. The carriage house is adorable! It is comfy, clean and quiet. It is stocked with a coffee maker, a toaster, an air fryer, a microwave, etc. If you need it, it probably there!I just cannot say enough about these hosts and their adorable carriage house rental. "
Carriage House Hideaway in Middle of Chestertown
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)
"Clean and away from all the hustle and bustle, not to mention the views and lovely hosts! Don’t miss out on this if you want a relaxing trip, or if you do want to explore the area there’s plenty of great small towns in the area, also an easy drive to some of the most iconic cities along the Chesapeake Bay."
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)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is AED 643
AED 1,159 total
includes taxes & fees
27 Apr - 28 Apr
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)
"The hosts were amazing and enjoyed talking with them. We look forward to coming back soon. Sean and Paula "
The price is AED 257
AED 409 total
includes taxes & fees
6 May - 7 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
24 Apr - 25 Apr
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, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
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)
"Thank you Lynn for having us. It was a short trip but worth it, especially being able to stay at the She Shed - clean, conveniently located, and quiet. We’ll definitely be back!"
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)
"Just spent the weekend at Knot’s Landing and highly recommend it! The location is incredible with walk-ability to all of Main St and still close to the marina and the beach. The place was very clean and incredibly spacious. Check in and out was perfectly smooth and the host was responsive and helpful with the one question we had. 10/10 absolutely recommend!"
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)
"We enjoyed our stay so much. It was so private and quiet. It was also nice to be able to bike ride where ever we needed to go. It was perfect!! We plan on going back soon!!"
Cute waterfront apartment -- 8 min from the beach!
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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.0 out of 10, Very Good, (1)
The price is AED 496
AED 1,032 total
includes taxes & fees
27 Apr - 28 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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.

9.4 out of 10, Exceptional, (22)
"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.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books

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

9.8 out of 10, Exceptional, (8)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
The price is AED 716
AED 837 total
includes taxes & fees
28 Apr - 29 Apr
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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: First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 9.3 mi/14.9 km from the heart of Kennedyville. Includes a private pool, laundry facilities, and free WiFi. A fitness center and an outdoor pool are on site. WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 9.4 mi/15.1 km away in Earleville. Free WiFi and Smart TVs are included. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace: It’s situated in Havre De Grace, 17.1 mi/27.5 km away. Includes free WiFi. Historic Downtown Garden Oasis with Private Patio: It’s located in Chestertown, 7.7 mi/12.4 km from Kennedyville. Includes free WiFi, outdoor space, and separate dining areas.
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.