Sort by:

Grid List

Show Map

Results 1 - 24 of 24
results for 'Vacation Rental'

A Modern Retreat: The Glanville

20361 Glanville Lane Rock Hall, Maryland 21661

Spectacular architectural gem facing west right onto The Chesapeake Bay. Enjoy the fully equipped house with central air conditioning and heating adjustable by areas, beautiful cherry flooring, all high end/designers appliances, custom built...


Banning House

109 South Queen Street Chestertown, Maryland 21620

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.


Bay View Beach House

5783 Beach Road Rock Hall, Maryland 21661

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

21017 Bayside Avenue Rock Hall, Maryland 21661

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.


Cliff Point Retreat

4670 Cliffs City Road Chestertown, Maryland 21620

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.


Coveside Cottage

12060 Spring Cove Road Rock Hall, Maryland 21661

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.


Elizabeth's Pond Retreat

6426 Elizabeths Lane Rock Hall, Maryland 21661

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–


Evergreen Knoll Cottages

130 1st Avenue Betterton, Maryland 21610

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.


Heron Pond Cottage

7820 Quaker Neck Road Chestertown, Maryland 21620

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.


InnTowne House

21309 East Sharp Street Rock Hall, Maryland 21661

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.


Lovely Cove Farm

232542 Lovely Lane Chestertown, Maryland 21620

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


Marsh Point Farm

13787 Shallcross Wharf Road Kennedyville, Maryland 21645

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.


River Lodge

219 Britland Farm Lane Chestertown, Maryland 21620

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.


Running Fox

23791 Ricauds Branch Road Chestertown, Maryland 21620

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.


Secret Garden on Main

5764 North Main Street Rock Hall, Maryland 21661


Sharp Street Retreat

21236 East Sharp Street Rock Hall, Maryland 21661

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..


Stepne Manor

406 South Cross Street Chestertown, Maryland 21620

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.


Summer House

5797 South Hawthorne Avenue Rock Hall, Maryland 21661

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.


Sunset Lodge

4480 Eastern Neck Road Rock Hall, Maryland 21661

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

20997 Haven Road Rock Hall, Maryland 21661

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.


The Beach Cottage

5791 Beach Road Rock Hall, Maryland 21661

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


The Kentfields Farm: A Country Estate

5793 Quaker Neck Landing Road Chestertown, Maryland 21620


The Lodge on Main

5718 North Main Street Rock Hall, Maryland 21661

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.


Welcome Aboard

5813 Clam Cove Rock Hall, Maryland 21661

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.