Entire home
Charming Waterfront home, Kent Island, Maryland!
Photo gallery for Charming Waterfront home, Kent Island, Maryland!





Reviews
9.09.0 out of 10
Wonderful
Highlights
- Ping pong on-siteA rare find — challenge friends and family to endless matches.
Popular amenities
- Barbecue
- Air-conditioning
- Onsite parking available
- Refrigerator
- Internet
- Washing machine
Explore the area

Chestertown, MD
- Island Dog ParkPlace, Island Dog Park3 min drive
- Paul Reed Smith GuitarsPlace, Paul Reed Smith Guitars4 min drive
- Northern Chesapeake BayPlace, Northern Chesapeake Bay5 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)58 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 King Bed, 3 Queen Beds and 2 Double Sofa Beds
3 bathrooms
Bathroom 1
Bathtub
Bathroom 2
Bathroom 3
Spaces
Porch or lanai
Add dates for prices
Similar properties

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (26 reviews)
9.8/10
Exceptional
(26 reviews)

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Chestertown
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Chestertown
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (325 reviews)
10/10
Exceptional
(325 reviews)

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (8 reviews)
9.8/10
Exceptional
(8 reviews)

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (114 reviews)
10/10
Exceptional
(114 reviews)

Private Cottage on gated estate
Arundel on the Bay
Private Cottage on gated estate
Arundel on the Bay
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.8 out of 10, Exceptional, (42 reviews)
9.8/10
Exceptional
(42 reviews)

Private Boat Dock! Wye River Retreat in Queenstown
Queenstown
Private Boat Dock! Wye River Retreat in Queenstown
Queenstown
- Pool
- Kitchen
- Washing machine
- Dryer
9.2 out of 10, Wonderful, (5 reviews)
9.2/10
Wonderful
(5 reviews)

Unwind by Waterfront in Annapolis w/pool&pier OR enjoy the wintry frozen river
Cape Saint Claire
Unwind by Waterfront in Annapolis w/pool&pier OR enjoy the wintry frozen river
Cape Saint Claire
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (61 reviews)
10/10
Exceptional
(61 reviews)

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.
Eastport
Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.
Eastport
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (35 reviews)
10/10
Exceptional
(35 reviews)

3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Herald Harbor
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Herald Harbor
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (43 reviews)
10/10
Exceptional
(43 reviews)

Waterfront Annapolis Cottage: Fire Pit & Pier
Annapolis
Waterfront Annapolis Cottage: Fire Pit & Pier
Annapolis
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.4 out of 10, Exceptional, (49 reviews)
9.4/10
Exceptional
(49 reviews)

Walk to Marinas, Dining & Shops, Outdoor Private Oasis with Fire pit & Seating
Rock Hall
Walk to Marinas, Dining & Shops, Outdoor Private Oasis with Fire pit & Seating
Rock Hall
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Queenstown
Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Queenstown
- Air-conditioning
- Parking available
- Laundry room
- Microwave
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (141 reviews)
10/10
Exceptional
(141 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville
- Pool
- Spa pool
- Free Wi-Fi
- Air-conditioning
10.0 out of 10, Exceptional, (224 reviews)
10/10
Exceptional
(224 reviews)

Bright 3BR Annapolis Home, Sleeps 8 – Minutes to Navy Stadium & USNA
Homewood
Bright 3BR Annapolis Home, Sleeps 8 – Minutes to Navy Stadium & USNA
Homewood
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (29 reviews)
9.6/10
Exceptional
(29 reviews)

Lots free parking, hot tub, outdoor oasis - NOT party house
Annapolis
Lots free parking, hot tub, outdoor oasis - NOT party house
Annapolis
- Spa pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (30 reviews)
9.6/10
Exceptional
(30 reviews)

Cottage with Harbor & Bay Views in Rock Hall close to everything
Rock Hall
Cottage with Harbor & Bay Views in Rock Hall close to everything
Rock Hall
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (70 reviews)
9.8/10
Exceptional
(70 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.4 out of 10, Exceptional, (96 reviews)
9.4/10
Exceptional
(96 reviews)

Eastport Bungalow | Yard, Grill & Walk Downtown
Eastport
Eastport Bungalow | Yard, Grill & Walk Downtown
Eastport
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (7 reviews)
10/10
Exceptional
(7 reviews)

Restful and Charming Home in Eastport
Eastport
Restful and Charming Home in Eastport
Eastport
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Charming cottage with Pool Access and WiFi in lovely Rock Hall
Rock Hall
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Rock Hall
- Pool
- Free Wi-Fi
- Air-conditioning
- Outdoor space
10.0 out of 10, Exceptional, (8 reviews)
10/10
Exceptional
(8 reviews)

Private 4BR Guest Cottage part of Estate, Magothy River Views, Near Annapolis
Arnold
Private 4BR Guest Cottage part of Estate, Magothy River Views, Near Annapolis
Arnold
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (6 reviews)
10/10
Exceptional
(6 reviews)

Heated pool, sandy beach, pier, and playground set punch point apart!
Sherwood
Heated pool, sandy beach, pier, and playground set punch point apart!
Sherwood
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)

Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Annapolis
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Annapolis
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (11 reviews)
10/10
Exceptional
(11 reviews)

Baydream Believer
Talbot County
Baydream Believer
Talbot County
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (89 reviews)
10/10
Exceptional
(89 reviews)

Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
Wittman
Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
Wittman
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.4 out of 10, Exceptional, (6 reviews)
9.4/10
Exceptional
(6 reviews)

Eastern Shore beach cottage get-away
Rock Hall
Eastern Shore beach cottage get-away
Rock Hall
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (143 reviews)
10/10
Exceptional
(143 reviews)

Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis
Annapolis
Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis
Annapolis
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (26 reviews)
10/10
Exceptional
(26 reviews)

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
- Spa pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (19 reviews)
9.6/10
Exceptional
(19 reviews)
About the area
Chester
Located in Chester, this holiday home is on the waterfront. Queenstown Harbor Golf and Bay Hills Golf Club are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Annapolis City Dock and Queenstown Premium Outlets. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.

Chestertown, MD
What's nearby
- Island Dog Park - 3 min drive - 3.2 km
- Paul Reed Smith Guitars - 4 min drive - 4.2 km
- Northern Chesapeake Bay - 5 min drive - 4.6 km
- Matapeake State Park - 7 min drive - 8.4 km
- Love Point State Park - 7 min drive - 9.6 km
Getting around
- Easton, MD (ESN-Easton - Newnam) - 29 min drive
Restaurants
- Chick-fil-A - 4 min drive
- McDonald's - 8 min drive
- McDonald's - 5 min drive
- Starbucks - 5 min drive
- Friendly Food Store - 5 min drive
Frequently asked questions
Is Charming Waterfront home, Kent Island, Maryland! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Charming Waterfront home, Kent Island, Maryland!?
On-site parking is available at the property.
What time is check-in at Charming Waterfront home, Kent Island, Maryland!?
Check-in begins at 4:00 PM.
What time is check-out at Charming Waterfront home, Kent Island, Maryland!?
Checkout is at 10:00 AM.
Where is Charming Waterfront home, Kent Island, Maryland! located?
Situated on the waterfront, this holiday home is 3 mi (4.8 km) from Island Dog Park and within 6 miles (10 km) of Chesapeake Exploration Center and Paul Reed Smith Guitars. Chesapeake Bay and Northern Chesapeake Bay are also within 6 miles (10 km).
Tell us how we can improve our siteShare feedback