House vacation rentals in Kent County

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Gorgeous home in town center & short walk to WAC

19th century home. NFL Sun Ticket! 55” TV in family room, 2 more. 1st floor primary with full bath. Hi speed internet. Pets welcome! In the historic district of Chestertown, 3 block walk from Wash College and the waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 bedrooms with queens. 100% cotton, 1000 thread count sheets and luxury mattresses. Loft connected to a 2nd story bedroom with queen bed. Fenced yard, acre of gardens. Fire pit. Weber grill

Cozy 3-bedroom home w/ Hot tub & 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.

The Patriot House-Chestertown, MD

Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.

Waterfront escape & walk to historic Chestertown

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

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.

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

NEW Chestertown Retreat

Enjoy this newly built (July 2023) semi-detached home with fresh furnishings, fully stocked with everything you need and private fenced back yard. 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, hunting trips, weddings or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

2 Beds, 2.5 Baths - Perfect Downtown Location

Charming and inviting, this beautifully updated home in historic Chestertown offers the perfect blend of comfort and location. Featuring 2 bedrooms—each with its own en suite bath—plus an additional half bath on the first floor, it comfortably accommodates up to 4 adults. Enjoy bright, thoughtfully designed living spaces throughout. Just a few blocks from downtown shops, restaurants, and waterfront, and an easy walk to Washington College.

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.