Vacation Rentals in Kent County, Maryland

Banning House is a beautifully restored single family home in the heart of historic Chestertown up the street from The Chester River. You can walk to everything or simply sit outside on your front porch and enjoy the neighborhood.

Watch sailboats by day and the lights of Baltimore by night as you enjoy the sunroom, or visit the beach located just steps from your front door. Complete with comfortable living room, a spacious kitchen, full bath, 2+ bedrooms and air conditioning.

Bayside Retreat has 3 bedrooms and 1 1/2 baths and is located a short walk away from great restaurants on the harbor. Guests also enjoy pool privileges at Rock Hall Landing Marina just 50 yards away.

This simple, water-front cottage is 10 miles outside of Chestertown on the Chester River. It has 3 bedrooms, 2 baths, a wood-burning fireplace and a fully equipped kitchen.

A fully equipped home for the most discerning guests. This brand-new home-away-from home supplies every amenity one could demand. Two bedrooms, 2 full baths with skylights, a full kitchen, dining nook, living room opening onto a full deck.

Just six minutes from the town of Rock Hall and 13 minutes from Chestertown, this completely renovated home on 5 mostly wooded acres features a large pond right in the back yard. 3 bedrooms and 2 1/2 baths, sleeps 6 - 8–

Waterfront vacation cottages on the beautiful Sassafras River with private beach and pier. Fantastic location for people who are looking for a secluded and serene vacation in the Chesapeake Bay area.

This comfortable quiet cottage is just a mile outside of historic Chestertown. It has two bedrooms and one bath and comes complete with linens and a fully equipped kitchen.

Upscale, modern and new two bedroom apartment overlooking Main St. in Rock Hall. Wonderful amenities, lots of space and full kitchen. $275 per night. Up to four guests. Two night minimum, weekly rates available. Includes breakfast at Java Rock.

A country estate located within 5 miles of Chestertown on the Jarrett Creek.

A screened porch which is steps from the dock that hosts two kayaks for guests use and a simple floating dock for entry/exit.

Vacation home for rent overlooking the Sassafras River. Property features a sandy shoreline. Home features two bedrooms, 1 full/2 half baths, and 3rd floor dorm room with views and 4 beds for kids.

With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination.

This countryside property with wildlife pond and woodside fields, includes a two-story historic house and barn. Ideal for romantic get-a-ways, retreats, hunting parties or a country wedding.

This charming home on Sharp Street in Rock Hall is a perfect place to stay for you and your family and friends. This recently renovated house sleeps 10 comfortably..

This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.

Located on one of the prettiest streets in Rock Hall, this 3 bedroom 1 bath house is within walking distance to restaurants and Rock Hall Harbor. A second floor loft bedroom and spacious backyard is perfect for the kids.

58-acre estate located on the Chesapeake Bay with a personal beach, offering stunning waterfront views and sunsets. Only 3 miles away from town and Eastern Neck Island.

Swan Creek Waterfront Cottage with large yard leading to 200'+ pier for boats, crabbing, and fishing. Explore the quaint town of Rock Hall with nearby restaurants, shopping and loads of outdoor activities.

Beach Front Cottage Get-A-Way Newly renovated, charming cottage with a sandy beach right across the quiet street. Beach is great for swimming, kayaking or just gazing at the boats passing by in the distance. Amazing Chesapeake Bay sunsets in the quai

Everything is crisp, clean and recently renovated. It sleeps up to 9 in three bedrooms and offers 2 full baths. The completely efficient kitchen offers an overlook on Main Street.

This lovely little get-away with a European flair is convenient to all the amenities of Rock Hall. Two bedroom, one bath, apartment has a master bedroom with private balcony.

Welcome Aboard is a 3 bedroom and 2 1/2 bath home in Rock Hall's Harbor Woods Community. A short walk to Main Street attractions and waterfront dining. Includes Wi-fi, linens, fully equipped kitchen, BBQ, and laundry. Fireplace in living room.