Vacation Rentals in Kent County, Maryland

1. 106 Church Alley

Historic District townhouse featuring stylish, modern updates offers a home base to unwind or celebrate with family and friends in a beautiful and highly walkable part of town.

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer.

3. 114 High Street Vacation Rental

Chestertown, Maryland

4. 200 High Street

Chestertown, Maryland

Bright and open 2 bedroom apartment in the heart of downtown Chestertown

5. Bayside Retreat

Rock Hall, Maryland

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.

6. Cottage On Kent

Chestertown, Maryland

Cottage On Kent is a charming guest cottage rental. It is located within walking distance to downtown, the Chester River and Washington College.

7. Coveside Cottage

Rock Hall, Maryland

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.

8. Downtown Apartment

Chestertown, Maryland

1 Bedroom Apartment 2 blocks from downtown Chestertown MD on a quiet residential street with one queen size bed.

9. InnTowne House

Rock Hall, Maryland

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.

10. Pilot House

Rock Hall, Maryland

11. River Lodge

Chestertown, Maryland

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.

12. Rolling View Farms, LLC

Chestertown, Maryland

Please consider staying with us when visiting historic Chestertown. Our five year young Rancher is ideally located within walking distance to Washington College and downtown. This fully equipped home offers the perfect getaway.

13. Ruby's Sea Glass Cottage LLC

Betterton, Maryland

Vacation Rental House in Betterton, MD

14. Sharp Street Retreat

Rock Hall, Maryland

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..

15. Stepne Manor

Chestertown, Maryland

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.

16. Sunset Lodge

Rock Hall, Maryland

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.

17. Swan Creek Waterfront

Rock Hall, Maryland

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.

18. The Beach Cottage

Rock Hall, Maryland

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

19. The Lodge on Main

Rock Hall, Maryland

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.

20. Thornton Estate

Chestertown, Maryland

Elegance and seclusion on 300+ acres - Thornton Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificient manor house anchors the 325 acre preserved farm minutes outside of Chestertown, MD.

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1. 106 Church Alley

2. 108 Annex

3. 114 High Street Vacation Rental

4. 200 High Street

5. Bayside Retreat

6. Cottage On Kent

7. Coveside Cottage

8. Downtown Apartment

9. InnTowne House

10. Pilot House

11. River Lodge

12. Rolling View Farms, LLC

13. Ruby's Sea Glass Cottage LLC

14. Sharp Street Retreat

15. Stepne Manor

16. Sunset Lodge

17. Swan Creek Waterfront

18. The Beach Cottage

19. The Lodge on Main

20. Thornton Estate

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