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Vacation Rentals in Kent County

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Our top choices for Kent County vacation rentals

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

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,618
￥19,530 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,458
￥24,801 total
includes taxes & fees
Jan 1 - Jan 2, 2026
First Floor Studio Apartment in Historic Chestertown
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is ￥27,325
￥48,626 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Waterfront Retreat with Private Dock and Beach
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥28,183
￥42,487 total
includes taxes & fees
Jan 19 - Jan 20, 2026
BAYSIDE BUNGALOW
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
The price is ￥35,132
￥65,045 total
includes taxes & fees
Dec 30 - Dec 31
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
High Tide Haven Suite

Vacation Home in Kent County

High Tide Haven Suite
The price is ￥27,051
￥31,173 total
includes taxes & fees
Dec 29 - Dec 30
High Tide Haven Suite
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Houseboat in Arnold

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
United States
Kedra B.
The price is ￥20,493
￥57,005 total
includes taxes & fees
Dec 30 - Dec 31
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Exterior
Luxe Houseboat: Breathtaking Skyline 360 Views

Houseboat in Baltimore

Luxe Houseboat: Breathtaking Skyline 360 Views
10.0 out of 10, Exceptional, (22)
"What an amazing experience. From check-in to check-out and everything in between, it was by far one of the best experiences I’ve had in a very long time! "
United States
Tie A.
The price is ￥45,085
￥94,289 total
includes taxes & fees
Dec 29 - Dec 30
Luxe Houseboat: Breathtaking Skyline 360 Views
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Houseboat in Baltimore

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, (11)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is ￥36,990
￥84,061 total
includes taxes & fees
Dec 28 - Dec 29
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Property grounds
Country Get Away 1 Bedroom Apartment

Apartment in Elkton

Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is ￥10,930
￥17,379 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Country Get Away 1 Bedroom Apartment
Marina
Cozy Fells Point Gem / In The Heart of Fells Point

Apartment in Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (200)
"Great place all around "
United States
Sophia F.
The price is ￥8,611
￥30,742 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Fells Point Gem / In The Heart of Fells Point
Marina
Historic Chesapeake City Stay

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is ￥12,682
￥38,669 total
includes taxes & fees
Dec 29 - Dec 30
Historic Chesapeake City Stay
1 bedroom, WiFi, bed sheets, wheelchair access
Restful Non-Shared Basement Suite In Harford MD

Vacation Home in Bel Air

Restful Non-Shared Basement Suite In Harford MD
10.0 out of 10, Exceptional, (2)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is ￥8,611
￥17,426 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Restful Non-Shared Basement Suite In Harford MD
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Vacation Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (93)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is ￥9,238
￥31,466 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ￥13,359
￥41,877 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
1 bedroom, desk, free WiFi, bed sheets
Lower Level Loft - Adorable Studio Apt. Near BWI

Vacation Home in South Gate

Lower Level Loft - Adorable Studio Apt. Near BWI
9.4 out of 10, Exceptional, (13)
"This was great for our stay. Nice place to come back to at the end of the day. It’s in a quiet neighborhood and being a lower level there is no traffic noise either. Great communication with the host and the description of the listing is accurate. Enjoy!"
United States
Jack B.
The price is ￥10,334
￥19,813 total
includes taxes & fees
Dec 28 - Dec 29
Lower Level Loft - Adorable Studio Apt. Near BWI
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Apartment in Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ￥28,183
￥52,445 total
includes taxes & fees
Dec 28 - Dec 29
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is ￥15,050
￥43,338 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming Coastal/Country Home w/3 Acres & Sauna!
Basic Apartment, Balcony, City View | Terrace/patio
1-BD Home near Stadiums Free Parking

Apartment in Pigtown

1-BD Home near Stadiums Free Parking
3.0 star property
7.6 out of 10, Good, (5)
"Great property. Loved coziness and location. Will book again in the future. Wish I could’ve had a broom available to clean better after myself. "
United States
Tallulah
The price is ￥15,814
￥22,260 total
includes taxes & fees
Dec 28 - Dec 29
1-BD Home near Stadiums Free Parking
Fridge, microwave, oven, stovetop
1Bed/Bath Apt in Baltimore 5 min to hospitals, coffee shops, Inner Harbor &more

Apartment in Downtown Baltimore

1Bed/Bath Apt in Baltimore 5 min to hospitals, coffee shops, Inner Harbor &more
9.6 out of 10, Exceptional, (13)
"Room was excellent no complaints. Will book again in the future. "
United States
Stephfone
The price is ￥9,864
￥29,478 total
includes taxes & fees
Dec 29 - Dec 30
1Bed/Bath Apt in Baltimore 5 min to hospitals, coffee shops, Inner Harbor &more
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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Top Kent County Hotel Reviews

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

10/10 Excellent
"I stay here a couple times a year and have never been disappointed. Everything from the staff, rooms, location and overall vibe of the hotel is outstanding."
Marc 2-night trip
Posted 18 hours ago
Hotel Ulysses, a Member of Design Hotels

Find out more about Kent County

Vacation Apartments in Kent County

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