House vacation rentals in Kent County

Find and book unique houses on Airbnb

Top-rated house rentals in Kent County

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 129 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

May 4 – 11

G$41,047 GYD per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 155 reviews

Fully refurbished historic house neat town center

Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.

Jan 18 – 25

G$73,134 GYD per night

Guest favorite

Home in Chestertown

4.96 out of 5 average rating, 72 reviews

Cozy 3-bedroom home w/ screened in porch & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Mar 19 – 26

G$43,124 GYD per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 104 reviews

Waterfront w/Pier &Walking Distance to Chestertown

This 4 bedroom, 3 bath waterfront home is a terrific place to enjoy time with family and friends. This home has amazing amenities; from the stylish updated renovations and furnishings (some antiques), the screened porch, patio, fire pit, hot tub (Oct - April), sporting equipment, to the spacious, comfortable, indoor & outdoor gathering spaces. The kitchen is well-appointed with gourmet appliances, and plenty of hosting and culinary supplies to savor wonderful meals together at the house.

Nov 9 – 16

G$96,498 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 18 reviews

Chesapeake Bay Retreat w/ Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

Sep 28 – Oct 5

G$76,420 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 65 reviews

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

Apr 10 – 17

G$41,390 GYD per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Nov 15 – 22

G$108,045 GYD per night

Guest favorite

Home in Chestertown

4.89 out of 5 average rating, 27 reviews

Beautifully remodeled home in Historic Chestertown

Discover Chestertown and stay in this charming, newly renovated 2 bd/1.5 bath family friendly house (part of Historic District). Can sleep 5 (2 queen beds, 1 twin). 4 min walk to the fountain park and the restaurants (Watershed, the Kitchen, Bad Alfred's, etc). 2 min drive/6min walk to Washington College. -No smoking (any kind) in the house. -No parties/gatherings. -Please no shoes in the bedrooms as they are carpeted. -Be aware of steep stairs.

Aug 3 – 10

G$38,916 GYD per night

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 102 reviews

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.

Sep 18 – 25

G$40,414 GYD per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 13 reviews

NEW Chestertown Retreat

Enjoy this brand new semi-detached home (construction completed in July 2023) with new furnishings and fully stocked with everything you need. Located less than 1/2 mile to Washington College and 1.5 miles to downtown, this home is close to everything Chestertown has to offer. Perfect for parents and families visiting students, or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

Feb 18 – 25

G$44,993 GYD per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 37 reviews

Waterfront house with private dock & kayaks!

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay. With 2 bedrooms and water views from nearly every room, it's the perfect retreat for relaxation and exploration.

Jul 11 – 18

G$54,133 GYD per night

Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 166 reviews

Historic Chestertown

Lovely home with great indoor-outdoor entertaining space. Fully renovated 3 bed, 2.5 bath. Top of the line open floor plan kitchen/family room. Located in Historic district on the main street only few blocks from restaurants, shops and river front. From May 15, 2022 through Oct 31, 2022 all weekend are a 3 day minimun

Sep 17 – 24

G$70,212 GYD per night