Queen Anne's Area Rentals
- From $243 per night (USD)
VRBO
Charming Chestertown Waterfront Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your stay in Chestertown in a waterfront home on a tidal creek that is only minutes from historic downtown and Was ...
From $243 per night (USD)VRBO
- From $1350 per night (USD)
Expedia
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, 5.5 bath wa ...
From $1350 per night (USD)Expedia
- From $578 per night (USD)
VRBO
Pool and Bay Views on wrap around deck in Kent Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The Pool is Open! Welcome to your pool house! This summer cottage with a private pool has views of the Chesapeake Bay! ...
From $578 per night (USD)VRBO
- From $346 per night (USD)
Expedia
New! Stylish downtown home w\/awesome outdoor area!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tastefully updated 3 bedroom home with everything you need to enjoy Kent Island! All new furniture and bedding! Home is ...
From $346 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Waterfront property on 3\/4 acres with private beach, pool, hot tub, and pier.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Sleeps 6. This is a 1450 sq ft, 2-bedroom unit on the ground floor of a two story duplex overlooking the expansive Chest ...
From $385 per night (USD)VRBO
- From $261 per night (USD)
Expedia
Secluded Waterfront Cottage on 200 acre farm near Queenstown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
4bedroom, 2 bathroom, air conditioned house on 200 acre farm with a mile of waterfront on Maryland's Eastern Shore. With ...
From $261 per night (USD)Expedia
- Click For Pricing
Expedia
Bentons Pleasure- Cox Creek, Pier and Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WATERFRONT - 4 Bed, 3 Bath Private house in the town of Chester is available for the 2021 rental season and is an amazin ...
Click For PricingExpedia
- Click For Pricing
Expedia
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Gray Fox Farm is a 135-acre, classic Chesapeake Bay-style estate located on the scenic (and largely undiscovered) Corsi ...
Click For PricingExpedia
- From $175 per night (USD)
VRBO
Cass-Away Luxury Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kent Narrows Rentals welcomes you aboard Cass-Away. A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a ...
From $175 per night (USD)VRBO
- From $456 per night (USD)
Expedia
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, wh ...
From $456 per night (USD)Expedia
- From $810 per night (USD)
VRBO
HUGE SANDBOX! Play Beach Volleyball by the Restaurant, Marina, and Beach Bar
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Kent Island Beach House LLC Location! BAYcation! STAYcation! Right on Kent Island in Stevensville MD. Come by Car, Boat, ...
From $810 per night (USD)VRBO
- From $788 per night (USD)
Expedia
Sunsets and 4 King Bedrooms - Sunny Isle of Kent Across the Water from Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Are you looking for a holiday by the bay, a small reunion, a family vacation, a getaway, a golf outing, a fishing trip, ...
From $788 per night (USD)Expedia
- From $475 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 $475 per night (USD)VRBO
- From $1099 per night (USD)
VRBO
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 10-12-PETS ALLOWED
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Weekend or weekly getaway in this 3000 SF house located in Kent Island MD, surrounded by the beautiful waters of the Che ...
From $1099 per night (USD)VRBO
- From $557 per night (USD)
VRBO
Kent Island Waterfront | Game Room | Pool | Private Dock | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious Home on Little Greenwood Creek Within Short Drive to Annapolis and Local Kent Island Beaches Only a short driv ...
From $557 per night (USD)VRBO
- From $850 per night (USD)
Expedia
Picturesque Panoramic View of Kentmorr Marina, Fishing Boats & Restaurant.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Kent Island Beach House II: A Fisherman's Village right in Kentmorr is not only a great place for the bride or groom's f ...
From $850 per night (USD)Expedia
- From $500 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 $500 per night (USD)VRBO
- Click For Pricing
Expedia
Kent Island - Gorgeous Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful waterfront property on 10 acres of land within a short drive to Annapolis and local Kent Island restaurants. ...
Click For PricingExpedia
- From $631 per night (USD)
VRBO
Private pier at Waterfront Kent Island home with Hot Tub (Open!)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this beautiful waterfront home with a private pier that sits only 50 feet back from the Chesapeake Bay. Locat ...
From $631 per night (USD)VRBO
- From $144 per night (USD)
Expedia
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 $144 per night (USD)Expedia
- From $813 per night (USD)
VRBO
Sprawling Waterfront Home, Dock & In-Home Theatre
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Winchester Creek Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $813 per night (USD)VRBO
- Click For Pricing
Expedia
Sudlersville -Very cute Newly renovated 3BR1BA rancher on 4.75 acres
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Brand new beautiful kitchen with granite counters, new cabinets and new appliances Small but efficient bathroom with new ...
Click For PricingExpedia
- From $429 per night (USD)
VRBO
Serenity on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Come relax and enjoy the peaceful water views and serene nature at this newly constructed 2 bedroom oasis in Kent Island ...
From $429 per night (USD)VRBO
- From $275 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 $275 per night (USD)Expedia
- From $783 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 $783 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Belle Blu of Kent Narrows Grasonville, Maryland
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located place in Grasonville, Maryland of Kent Narrows. Feature 1200 squar ...
From $450 per night (USD)VRBO
- Click For Pricing
VRBO
Come explore Maryland's Eastern Shore. Near Annapolis, Wash. D.C. and Baltimore
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful A frame chalet on Kent Island. Open concept, spacious bedrooms, multiple decks and fenced in back yard. A shor ...
Click For PricingVRBO
- From $356 per night (USD)
VRBO
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We always clean and disinfect the home using extra cleaning recommendations from the Centers for Disease Control and Pre ...
From $356 per night (USD)VRBO
- From $950 per night (USD)
VRBO
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 26
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $950 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Relax on the Eastern Shore of Kent Narrows in a King Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Spacious vacation rental with king sized bed and all the comforts of home. Large kitchen and living room. Queen sized sl ...
From $165 per night (USD)VRBO
- From $975 per night (USD)
VRBO
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Contemporary home recently renovated on the Chesapeake Bay with pool, dock with 3’ at mean tide. Hugh master suite with ...
From $975 per night (USD)VRBO
- Click For Pricing
VRBO
Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Located on the Wye River with easy access to the bay, our cottage is perfect for your vacation. Lay out on our lawn, wa ...
Click For PricingVRBO
- From $2520 per night (USD)
VRBO
Beautiful Waterfront Estate
- Bedrooms:
- 9
- Bathrooms:
- 11
- Sleeps:
- 30
Brittland Manor was built in 1938 and sits on 530 riverside acres. When you drive up the long curved lane you are surro ...
From $2520 per night (USD)VRBO
- From $555 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 $555 per night (USD)VRBO
- From $445 per night (USD)
VRBO
Island Life! Kent Island Waterfront with Pool-Bring your boat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up t ...
From $445 per night (USD)VRBO
- From $613 per night (USD)
VRBO
ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax on the expansive deck of this adult only Chesapeake Bay front cottage and enjoy the sunsets from it's grand great ...
From $613 per night (USD)VRBO
- From $416 per night (USD)
VRBO
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 $416 per night (USD)VRBO
- From $925 per night (USD)
VRBO
Chesapeake Bay Waterfront ARTectural Home
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can i ...
From $925 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Get Away To The Beautiful Wye River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
We hope you will visit our family-friendly vacation home on Maryland's Eastern Shore of the Chesapeake Bay. The home in ...
From $370 per night (USD)VRBO
- From $128 per night (USD)
VRBO
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacu ...
From $128 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Luxurious Waterfront Kent Island Home 30 miles from Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy this beautiful contemporary home in a gated, waterfront community for a perfect getaway! This is a rare find! This ...
From $475 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Cape Cod Bed and Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Second floor bed and bath with private entrance and deck located in Chesapeake Bay community. Includes 2 extra long twi ...
From $150 per night (USD)VRBO
- From $125 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 $125 per night (USD)VRBO
- From $517 per night (USD)
VRBO
Waterfront on Kent Island
- Bedrooms:
- 2
- 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 $517 per night (USD)VRBO
- From $795 per night (USD)
VRBO
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful waterfront home with resort-like atmosphere just one hour from DC and Baltimore. Includes fastest high speed ...
From $795 per night (USD)VRBO
- From $299 per night (USD)
VRBO
5 bedroom Historic Victorian by Chester River
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...
From $299 per night (USD)VRBO
- From $375 per night (USD)
Expedia
25-50% Off~Private Beach~Hot Tub~Fire Table~
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities i ...
From $375 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Waterfront Millington Vacation Rental w\/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 10
Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...
From $409 per night (USD)VRBO
- From $592 per night (USD)
Expedia
Harbor View Haven | Waterfront w\/ Dock + HOT TUB!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BNB Breeze Presents Harbor View Haven! This exquisite waterfront property offers a captivating retreat to relax and rec ...
From $592 per night (USD)Expedia
- Click For Pricing
Expedia
Private\/Waterfront\/Gym\/Theatre\/Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy Resort-Style living in your suite located on the lowest level of the riverfront estate. Down one flight of exteri ...
Click For PricingExpedia
- From $1100 per night (USD)
Expedia
The Colonial Farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic pr ...
From $1100 per night (USD)Expedia
- From $1100 per night (USD)
VRBO
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
- Bedrooms:
- 7
- 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 $1100 per night (USD)VRBO
- From $489 per night (USD)
Expedia
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy Kent Island Time with waterfront views of Crab Alley Bay and Gorgeous Sunsets. Catch Crabs right from your pier an ...
From $489 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Floating condo with private beach, on the bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Just bring your sea legs! Enjoy the sounds and prime views of the bay and nature when you stay in this unique yacht moor ...
From $275 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Lovely, Recently-Renovated Home in Chestertown which sleeps 7.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" ...
From $199 per night (USD)Expedia
- From $149 per night (USD)
VRBO
Private, cozy guest house with luxury king suite
- 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 $149 per night (USD)VRBO
- From $595 per night (USD)
VRBO
Bayfront escape with screened porch, WFH desk, dock & views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Pier Pleasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $595 per night (USD)VRBO
- From $317 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 $317 per night (USD)VRBO
- Click For Pricing
VRBO
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy yet modern rancher equipped with 3 bedrooms, 2 baths, and spacious open floor plan! Whether you’re looking to be cl ...
Click For PricingVRBO
- From $329 per night (USD)
VRBO
Cass-N-Reel Luxury Houseboat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With one bedroom, on ...
From $329 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Three Decks overlook Marina basin and views of the Chesapeake and Eastern Bays
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Picturesque views from three decks and 3 bedrooms; additional 3 bedrooms. Walk to beach, large entertaining room with p ...
From $750 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Fish to the Left of Me, Geese to the right, Stuck in the middle w\/ Goats
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fisherman - Hunter - Outdoorsman Delight Working Goat Farm on the Cox Creek Your own Pier w/ Lift - you can simply boa ...
From $200 per night (USD)VRBO
- From $709 per night (USD)
VRBO
Waterfront family resort Lodge with private pier, game room and bar
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to the waterfront Twin Ponds Lodge, built in 1987 and for many of its years was used as overnight accommodations ...
From $709 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our brand-new coastal cottage, a haven for your perfect getaway. This charming home boasts a quintessential c ...
From $513 per night (USD)VRBO
- From $131 per night (USD)
VRBO
Cozy Waterfront Apartment Chester, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy th ...
From $131 per night (USD)VRBO
- From $505 per night (USD)
VRBO
Apartment with Lounge Stevensville, MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully renovated 1 bedroom, 1.5 bath apartment with attached lounge! 1 set of bunk beds with two full size mattress ...
From $505 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
- Bedrooms:
- 3
- 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 $400 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
\n3 bedroom bayfront oasis with spectacular views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
About this space Forget your worries in this spacious and serene space provides you with ample opportunity to unwind and ...
Click For PricingVRBO
- From $1051 per night (USD)
VRBO
Paradise on Kent Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PLEASE NOTE: If you request to book this property, you will be contacted by Annapolis Accommodations to finalize your ...
From $1051 per night (USD)VRBO
- From $500 per night (USD)
VRBO
family friendly nice quiet neighborhood close to most major cities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
a stay at my property would be like a retreat a get away from the madness from being in the city where u dont have to wo ...
From $500 per night (USD)VRBO
- From $1105 per night (USD)
VRBO
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This 4,600 square-foot, 6-bedroom, 4.5-bathroom Long Creek waterfront on over 2.6 acres of private land was designed wit ...
From $1105 per night (USD)VRBO
- From $217 per night (USD)
Expedia
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 $217 per night (USD)Expedia
- Click For Pricing
VRBO
Mount Vernon Apartment Rear
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 2
Featuring a garden and a terrace, Mount Vernon Apartment Rear provides accommodations in Baltimore with free WiFi and ga ...
Click For PricingVRBO
- From $265 per night (USD)
Expedia
Farm Stay at Lansdowne Manor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lansdowne Manor, some of the best preserved history of the late 18th/early 19th century on the Eastern Shore. ...
From $265 per night (USD)Expedia
- From $1007 per night (USD)
VRBO
Kent Island Luxary Home W\/ Pool and walking distance from the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This exquisite residence is a haven of luxury and relaxation, boasting a private pool and four spacious bedrooms with in ...
From $1007 per night (USD)VRBO
- From $713 per night (USD)
Expedia
Waterfront home with private pier is A Shore Thing
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
This beautiful custom waterfront home on Cox Creek on the Eastern Shore in Chester, MD awaits you with its gorgeous wate ...
From $713 per night (USD)Expedia
- Click For Pricing
Expedia
Stay on the Water at Kent Island Time
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax with the whole family and watch the world sail by from the living room and bedroom. The local ospreys will talk to ...
Click For PricingExpedia
- From $1290 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 $1290 per night (USD)Expedia
- From $394 per night (USD)
VRBO
Peaceful Queenstown Home w\/ Deck & Grill!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the charms of Queenstown, Maryland, with a stay at this lovely 4-bedroom, 2.5-bath vacation rental! Packed with ...
From $394 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Caribbean Oasis with Pool Home - 25 mins to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This exquisite Eastern Shore residence is perfect for relaxation and a quick trip to the beach or Annapolis, bo ...
From $209 per night (USD)Expedia
- From $176 per night (USD)
VRBO
Gorgeous Creek Side Ranch-Style Estate With Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Summary: Welcome to our Chesapeake Oasis! Quiet Queenstown is a beautiful and historic part of Maryland's Eastern Shore ...
From $176 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Spacious, family-friendly home; vast outdoor space on the water w\/ private dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The vacation of your dreams awaits at this bayfront beauty. Large enough for the whole family to enjoy and boasting a da ...
From $700 per night (USD)Expedia
- From $474 per night (USD)
VRBO
Waterfront Cottage on the Eastern Shore
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Kentmorr Cottage! We are so excited to have you as guests and we hope you send our concierge a direct mes ...
From $474 per night (USD)VRBO
- From $318 per night (USD)
Expedia
River Front, Private Single Family Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Soak in the waterfront hot tub or sit around the fire pit in this one story completely renovated house with 3 bedrooms a ...
From $318 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Kent Island Waterfront Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kent Island waterfront cottage situated perfectly for stunning western sunset views across the waters of Cox & Thompson ...
From $200 per night (USD)VRBO
- From $346 per night (USD)
Expedia
Coastal Kent Narrows Home on Bay\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this newly renovated home on Kent Island! This place is located right in the heart of the action and is walki ...
From $346 per night (USD)Expedia
- From $512 per night (USD)
VRBO
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This private coastal decorated home, nestled in a serene 5-acre wooded lot, is less than 5 miles from the Bay Bridge. ...
From $512 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Waterfront Sunset Bayview: sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent dir ...
From $450 per night (USD)Expedia
- From $3303 per night (USD)
VRBO
Exquisite 14,000 sq ft Waterfront Mansion with Pool
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Indulge in splendor at this sprawling 14,000-square-foot waterfront villa, spread out over 15 acres of Bayfront shorelin ...
From $3303 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You can explore the Eastern Shore's cuisine within a 5 minute drive to Kent Narrows. Enjoy a relaxing fishing trip with ...
From $175 per night (USD)Expedia
- From $89 per night (USD)
VRBO
❤️Charming Coastal\/Country Home w\/3 Acres & Sauna!❤️
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home with 3 acres of outdoor living! Perfect for Families ...
From $89 per night (USD)VRBO
- From $121 per night (USD)
Expedia
Relax on Kent Island in 3 Bedroom Home w\/Waterview
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Enjoy your vacation in this Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room and kitchen! Perfe ...
From $121 per night (USD)Expedia
- From $950 per night (USD)
VRBO
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
*NEW In-ground Large private pool! * An oasis from the stressors of everyday life, this exceptional 5 bedroom, 6 bathro ...
From $950 per night (USD)VRBO
- From $800 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 $800 per night (USD)Expedia
- From $416 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 $416 per night (USD)VRBO
- From $711 per night (USD)
Expedia
Private pier and pool at this waterfront Chestertown home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet ...
From $711 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This exceptional 5-bedroom, 3-bathroom shore house sits on a 1+ acre waterfront lot and boasts endless nautical activiti ...
From $550 per night (USD)VRBO
- Click For Pricing
Expedia
Kent Island waterfront spectacular Chesapeake Bay view
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We hope you will enjoy our newly renovated waterfront home as much as we do. Family friendly environment, bird watchi ...
Click For PricingExpedia