Queen Anne's Area Rentals
From $360 per night (USD)VRBO
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Enjoy your vacation in this Stylish 4 Bedroom Home with a view of the Chesapeake Bay from living room and kitchen! Perfe ...
From $360 per night (USD)VRBO
From $218 per night (USD)VRBO
Eastern Shore Get Away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Located on Maryland's Eastern Shore, on the Chester River, this fully furnished 1 bedroom, 1 bathroom apartment has all ...
From $218 per night (USD)VRBO
From $542 per night (USD)VRBO
Waterfront on Kent Island
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened ...
From $542 per night (USD)VRBO
From $1043 per night (USD)Expedia
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful waterfront home with resort-like atmosphere just one hour from DC and Baltimore. Includes fastest high speed ...
From $1043 per night (USD)Expedia
From $377 per night (USD)VRBO
5 bedroom Historic Victorian by Chester River
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...
From $377 per night (USD)VRBO
From $313 per night (USD)Expedia
Charming Coastal/Country Home w/3 Acres & Sauna!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy your vacation in this Stylish Coastal-Country Home with 3 acres of outdoor living! Perfect for Families & Weddings ...
From $313 per night (USD)Expedia
From $2121 per night (USD)VRBO
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
This short-term rental has an occupancy of 16 individuals with a max. of 12 guests being 18 years or older. Experience ...
From $2121 per night (USD)VRBO
From $750 per night (USD)Expedia
Private Pool & Stunning Bay Views on Kent Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Experience the Difference: Professionally Managed by iTrip Annapolis Kent Island Chesapeake Bay Cottage with Private Po ...
From $750 per night (USD)Expedia
From $97 per night (USD)VRBO
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacu ...
From $97 per night (USD)VRBO
From $477 per night (USD)VRBO
Wye River Cape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
At "Our Cove on the Wye" this is truly Chesapeake Country and your family memories can be made here. Canoe, kayak or ...
From $477 per night (USD)VRBO
From $300 per night (USD)VRBO
Secluded Waterfront Cottage on 200 acre farm near Queenstown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4bedroom, 2 bathroom, air conditioned house on 200 acre farm with a mile of waterfront on Maryland's Eastern Shore. With ...
From $300 per night (USD)VRBO
From $1072 per night (USD)Expedia
Waterfront 4 BR home with private pier and boat dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The waterfront house has 4BR and 4BA with 3900 sq ft + a two car garage. It has the benefits of both protected water fo ...
From $1072 per night (USD)Expedia
From $779 per night (USD)VRBO
Charming 3 Bedroom 3 Bath Beach Front Property
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This home is situated next to Kent Point Marina at the Southern most tip of Kent Island. If you enjoy crabbing, fishing ...
From $779 per night (USD)VRBO
From $1556 per night (USD)Expedia
Chesapeake Bay Waterfront Retreat with private pool! The Shore at it's best!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
*NEW In-ground Large private pool and Pier! * An oasis from the stressors of everyday life, this exceptional 5 bedroom, ...
From $1556 per night (USD)Expedia
From $709 per night (USD)VRBO
Grasonville Home w/ Private Pool on the Water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Become enveloped by Maryland hospitality when you stay at ‘The Winchester,’ a gorgeous home right on the water. With stu ...
From $709 per night (USD)VRBO
From $532 per night (USD)Expedia
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire t ...
From $532 per night (USD)Expedia
From $1576 per night (USD)VRBO
Chesapeake Bay Waterfront ARTectural Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
SPECIAL RATES FOR JANUARY AND FEBRUARY 2026! CHECK CALENDAR. Welcome to this most relaxing home for your getaway. Perfe ...
From $1576 per night (USD)VRBO
From $622 per night (USD)VRBO
The Lazy River House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...
From $622 per night (USD)VRBO
From $992 per night (USD)VRBO
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This short-term rental has an occupancy of 10 individuals with a max. of 8 guests being 18 years or older. Working Farm ...
From $992 per night (USD)VRBO
From $1450 per night (USD)Expedia
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Kent Island Beach House LLC Welcome to the original Kent Island Beach House offering comfortable water view accommodatio ...
From $1450 per night (USD)Expedia
From $573 per night (USD)VRBO
Circa 1700 Chesapeake Colonial home on the National Register.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Over 3000sf. Fully stocked, (just remodeled) kitchen, study, formal dining room, large living room, full bath, all down ...
From $573 per night (USD)VRBO
From $1077 per night (USD)Expedia
Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Perfect Escape! This exceptional 5-bedroom, 3-bathroom shore house sits on a 1+ acre waterfront lot and boasts endl ...
From $1077 per night (USD)Expedia
From $702 per night (USD)VRBO
Love Point Waterfront Home....Chesapeake Bay views....Pets OK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Maryland’s Chesapeake Bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and ...
From $702 per night (USD)VRBO
From $1387 per night (USD)Expedia
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
KI Beach House II: Over 2000 sq ft 4 bedroom/2 bath home is a modern fisherman's village on the corner by the marina. ...
From $1387 per night (USD)Expedia
From $542 per night (USD)VRBO
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened ...
From $542 per night (USD)VRBO
From $245 per night (USD)VRBO
Serene Waterfront Apartment on Kent Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located across the bay from Annapolis (just 1.5 miles from the bridge), we offer a convenient, quiet, and beautiful alte ...
From $245 per night (USD)VRBO
From $528 per night (USD)VRBO
Private Pier at Multi-Suite Waterfront Home on the Bay with Hot Tub (Open!)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this beautiful waterfront home with a p ...
From $528 per night (USD)VRBO
From $389 per night (USD)Expedia
Kent Island Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $389 per night (USD)Expedia
From $882 per night (USD)VRBO
Kent Island Luxury Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $882 per night (USD)VRBO
From $1067 per night (USD)Expedia
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Ideal felicity and perfection! This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with y ...
From $1067 per night (USD)Expedia
From $534 per night (USD)VRBO
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We pride ourselves on keeping our family vacation home very neat and clean. We will meet you to check you in, give you a ...
From $534 per night (USD)VRBO
From $690 per night (USD)Expedia
240' Private Beachfront @Kent Island Love Point - Great for Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 23
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $690 per night (USD)Expedia
From $206 per night (USD)VRBO
Adorable two-bedroom retreat close to Easton, Denton, Centreville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax in this quiet, renovated bungalow just a short bike ride to Tuckahoe State Park, the Eastern Shore's largest state ...
From $206 per night (USD)VRBO
From $1646 per night (USD)Expedia
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
This short-term rental has an occupancy of 14 individuals with a max. of 6 guests being 18 years or older. Experience t ...
From $1646 per night (USD)Expedia
From $243 per night (USD)VRBO
Cozy, unique, historic registered cottage on the Corsica River!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Captains Quarters was built in 1880 by local waterman, Captain John H. Osman. The Captain built 4 identical houses f ...
From $243 per night (USD)VRBO
From $1336 per night (USD)Expedia
The Colonial Farmhouse with Private Boat Rental
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic pr ...
From $1336 per night (USD)Expedia
From $1079 per night (USD)VRBO
Waterfront Estate w Private Pier, Game Room & Bar
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to the waterfront Twin Ponds Lodge, built ...
From $1079 per night (USD)VRBO
From $1516 per night (USD)Expedia
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
Set on 6 acres overlooking the beautiful Corsica River amidst idyllic farms, your home away from home calls. A 5-bedroom ...
From $1516 per night (USD)Expedia
From $999 per night (USD)VRBO
Three Decks overlook Marina basin and views of the Chesapeake and Eastern Bays
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Picturesque views from three decks and 3 bedrooms; additional 3 bedrooms. Walk to beach, large entertaining room with p ...
From $999 per night (USD)VRBO
From $408 per night (USD)Expedia
Family Retreat at Lansdowne Manor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Historic country manor located in a private tranquil setting, surrounded by mature trees & nature. Lansdowne is on the N ...
From $408 per night (USD)Expedia
From $586 per night (USD)VRBO
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recha ...
From $586 per night (USD)VRBO
From $523 per night (USD)Expedia
Bayou on the Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This exceptional bayfront retreat boasts breathtaking views and contemporary elegance, making it an ideal escape. Situat ...
From $523 per night (USD)Expedia
From $500 per night (USD)VRBO
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 8
Relax with the whole family at this peaceful secluded property. Located on the Chester River in Millington, MD, Pine For ...
From $500 per night (USD)VRBO
From $183 per night (USD)VRBO
Cozy Waterfront Apartment Chester, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Only accepting bookings from travel healthcare workers* *We live on the property* NO SMOKING OF ANY KIND is p ...
From $183 per night (USD)VRBO
From $602 per night (USD)VRBO
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our coastal cottage, a haven for your perfect getaway in a community that offers 3 different locations to acc ...
From $602 per night (USD)VRBO
From $311 per night (USD)Expedia
Chesapeake Houseboat Getaway on Kent Island, Maryland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for a peaceful waterfront, floating experience on the Chesapeake Bay? Julia’s Arc has got you covered. Easy acce ...
From $311 per night (USD)Expedia
From $756 per night (USD)VRBO
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Recently updated 4 bedroom home in a centralized, quiet, location with no shortage of amazing views of the Chesapeake Ba ...
From $756 per night (USD)VRBO
From $723 per night (USD)Expedia
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Recently upgraded heating, ventilation and air conditioning with new ductless system. This private coastal decorated ho ...
From $723 per night (USD)Expedia
From $289 per night (USD)VRBO
Lovely Home in Chestertown - Free EV Charging for guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" ...
From $289 per night (USD)VRBO
From $381 per night (USD)VRBO
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your peaceful riverfront getaway. This home sits directly on the water and is designed for slow mornings, bea ...
From $381 per night (USD)VRBO
From $540 per night (USD)VRBO
HGTV quality, private guest suite, country getaway with hot tub & fire pit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
A nature lovers dream! Kick back and relax in this tranquil, cozy space, with picture perfect sunsets, surrounded by nat ...
From $540 per night (USD)VRBO
From $1440 per night (USD)Expedia
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Relax and unwind at this spa-like luxury waterfront estate. Located on the Chesapeake Bay, this newly constructed vacati ...
From $1440 per night (USD)Expedia
From $417 per night (USD)VRBO
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk ...
From $417 per night (USD)VRBO
From $961 per night (USD)VRBO
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Chessie Cottage on The Bay! There is an intangible quality to a cottage coming from a unique combination of ...
From $961 per night (USD)VRBO
From $569 per night (USD)VRBO
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 ho ...
From $569 per night (USD)VRBO
From $331 per night (USD)Expedia
Floating 2 bed 2 bath condo stunning views of the bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
A truly unique experience, Enjoy the stunning view of the bay and nature staying on this 40 ft yacht moored at a fishing ...
From $331 per night (USD)Expedia
From $457 per night (USD)VRBO
Welcome to The Blue Crab House Stevensville Maryland Eastern Shore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome To The Blue Crab House Full of your finest eastern shore charm in Stevensville Maryland this spacious 3 bedroo ...
From $457 per night (USD)VRBO
From $936 per night (USD)Expedia
Kent Island Waterfront | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
New Hot Tub available late June 2026. Relax and unwind. Located on the Chesapeake Bay, this charming vacation rental fe ...
From $936 per night (USD)Expedia
From $607 per night (USD)VRBO
House on the Bay with Private Beach Access & Panoramic Bridge Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Stunning views and your own sandy beach! Relax wit ...
From $607 per night (USD)VRBO
From $640 per night (USD)Expedia
Island Blue Getaway! Charming family friendly Home on Kent Island MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Kent Island from this 3-bedroom house. Built in 2024, this fantastic property offers a king bed, ...
From $640 per night (USD)Expedia
From $571 per night (USD)VRBO
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing g ...
From $571 per night (USD)VRBO
From $324 per night (USD)Expedia
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the peace and tranquility at "Outrange," Blue Heron Farm's recently updated cabin. While we are new to VRBO, we h ...
From $324 per night (USD)Expedia
From $417 per night (USD)VRBO
Blue Heron Farm Waterfront Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of ...
From $417 per night (USD)VRBO
From $1412 per night (USD)Expedia
Kent Island Waterfront | Game Room | Private Dock | Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Soar above the everyday. Vacation like a legend. This waterfront oasis in Queen Anne's County offers an escape that ble ...
From $1412 per night (USD)Expedia
From $930 per night (USD)VRBO
Beautiful Kent Island Getaway with Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
PRIME LOCATION! MILE FROM CHEASPEAKE BEACH CLUB. This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your ...
From $930 per night (USD)VRBO
From $400 per night (USD)Expedia
Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3BR/2BA Home on 1 Acre – Peaceful Escape Near Beaches & Trails Escape to comfort and tranquility in this beaut ...
From $400 per night (USD)Expedia
From $1798 per night (USD)VRBO
Private Boat Dock! Wye River Retreat in Queenstown
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Expansive Outdoor Relaxation Space | Sunroom w/ Views | Pet Friendly w/ Fee Dive into waterfront fun when you stay at t ...
From $1798 per night (USD)VRBO
From $866 per night (USD)Expedia
Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Charming Kent Island Retreat – 4 BR • 2.5 BA • Pool Table • Near the Water ""Brand New Construction"" Escape to the East ...
From $866 per night (USD)Expedia
From $447 per night (USD)VRBO
Crab Alley | Waterfront Home + Hot Tub + Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Ch ...
From $447 per night (USD)VRBO
From $852 per night (USD)VRBO
Kent Narrows Waterfront 2 Acre Retreat. Sauna + Fire Pit. Endless water views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to The Cove at Heron Point, a private 2-acre waterfront retreat in the heart of Kent Narrows. Minutes from great ...
From $852 per night (USD)VRBO
From $596 per night (USD)VRBO
Kent Island Getaway with Fire Pit Near Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy an easy Eastern Shore escape at this spacious Kent Island home in historic Stevensville. With approximately 1,812 ...
From $596 per night (USD)VRBO
From $393 per night (USD)VRBO
Private & Peaceful Water Views, Big Deck, Games
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Down a gravel drive, surrounded by trees, with no neighbors in sight and water views from the deck. This home ...
From $393 per night (USD)VRBO
From $312 per night (USD)VRBO
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private 1-Bedroom Retreat in Chestertown, MD Skip the traditional hotel and enjoy your own private 1-bedroom, full-bath ...
From $312 per night (USD)VRBO
From $445 per night (USD)Expedia
Welcome to the secluded waterfront oasis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked along the water edge Riverfront Romance is a secluded couple oasis Designed for rest, connection, and quiet lux ...
From $445 per night (USD)Expedia
From $643 per night (USD)VRBO
NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your home away from home while you visit Stevensville/Kent Island! This 7 yr new home and BRAND NEW, as of May 2026, to ...
From $643 per night (USD)VRBO
From $1054 per night (USD)Expedia
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Stay comfortably in Stevensville at this 5-bedroom country house. Four king beds and 2 twin bed offer plenty of space fo ...
From $1054 per night (USD)Expedia
From $989 per night (USD)VRBO
*Waterfront* 5BR w/ Pool + Firepit on Kent Island!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
FEATURED IN BETHESDA MAGAZINE JULY ‘26 ISSUE ⭐THE HIGHLIGHTS • Private waterfront setting on Kent Island • Resort- ...
From $989 per night (USD)VRBO
From $746 per night (USD)Expedia
Waterfront Escape with Pool Nature Lover Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover the perfect blend of relaxation and adventure at our stunning waterfront home. With breathtaking water views, a ...
From $746 per night (USD)Expedia
From $510 per night (USD)VRBO
Riverside at Pear Tree Point--Waterfront Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Pear Tree Point, a peaceful waterfront retreat near historic Chestertown, Maryland. Perfect for families, cou ...
From $510 per night (USD)VRBO
From $897 per night (USD)VRBO
Luxury Waterfront Escape with Swim Spa, Sauna, Game Room, Beach Access, Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to Oyster Bay Getaway- the Pearl of Kent Island invites you to Indulge in the ultimate waterfront escape. This lu ...
From $897 per night (USD)VRBO
From $270 per night (USD)VRBO
Bay House Retreat. Main House + Guesthouse. Waterfront, spacious, private dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to the Bay House, a peaceful waterfront retreat with panoramic views and unforgettable sunsets of the Chesapeake ...
From $270 per night (USD)VRBO