Queen Anne's Area Rentals
- From $58 per night (USD)
VRBO
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 $58 per night (USD)VRBO
- From $1160 per night (USD)
Expedia
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best ...
From $1160 per night (USD)Expedia
- 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 $536 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 $536 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 $104 per night (USD)
Expedia
❤️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 $104 per night (USD)Expedia
- 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 $264 per night (USD)
Expedia
Country Estate in Historic District
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $264 per night (USD)Expedia
- From $1320 per night (USD)
VRBO
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 $1320 per night (USD)VRBO
- From $98 per night (USD)
Expedia
First Floor Studio Apartment in Historic Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everyt ...
From $98 per night (USD)Expedia
- 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 $643 per night (USD)
VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $643 per night (USD)VRBO
- 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 $235 per night (USD)
VRBO
Chestertown's Pet-Friendly Little Red Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and ...
From $235 per night (USD)VRBO
- From $350 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 $350 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 $350 per night (USD)
VRBO
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every ...
From $350 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 $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 $425 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 $425 per night (USD)VRBO
- From $385 per night (USD)
Expedia
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)Expedia
- From $275 per night (USD)
VRBO
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 $275 per night (USD)VRBO
- 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
- From $800 per night (USD)
VRBO
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)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 $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 $1700 per night (USD)
VRBO
Blake House Historic Estate with Private Inn
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Blake House represents one of the oldest colonial homes in Maryland, built by British settler, Charles Blake, o ...
From $1700 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 $389 per night (USD)
Expedia
Hidden gem with water and golf course views! Bike ride to downtown!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Relax by the fire pit and watch the sun set over the pond and golf course! If you like birdwatching, we have amazing gre ...
From $389 per night (USD)Expedia
- 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 $650 per night (USD)
VRBO
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philade ...
From $650 per night (USD)VRBO
- From $390 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 $390 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
- 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 $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
- From $550 per night (USD)
VRBO
The Lazy River House
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...
From $550 per night (USD)VRBO
- 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 $450 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 $450 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, Deck, ...
From $365 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 $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 $711 per night (USD)
VRBO
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)VRBO
- From $475 per night (USD)
Expedia
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)Expedia
- 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 $550 per night (USD)
Expedia
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)Expedia
- From $486 per night (USD)
VRBO
Beautiful Chesapeake Bay Views -pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Maryland’s Chesapeake bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and ...
From $486 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 $475 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 $475 per night (USD)VRBO
- From $155 per night (USD)
Expedia
Carriage House Hideaway in Middle of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $155 per night (USD)Expedia
- From $552 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 $552 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 $850 per night (USD)
VRBO
Away at the Bay: New Home on the Chesapeake Bay!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walki ...
From $850 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic C ...
From $275 per night (USD)Expedia
- From $775 per night (USD)
VRBO
Breathtaking waterfront home on the Chester River
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated ent ...
From $775 per night (USD)VRBO
- From $1700 per night (USD)
Expedia
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Imagine waking up to a back and front yard nature surrounded by pine trees and a Olympic pool. Home with all glass door ...
From $1700 per night (USD)Expedia
- From $619 per night (USD)
VRBO
River Lodge, Casual Riverfront setting
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get ...
From $619 per night (USD)VRBO
- From $619 per night (USD)
Expedia
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 $619 per night (USD)Expedia
- From $295 per night (USD)
VRBO
KENT ISLAND - Everything The Narrows has to offer you!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our exquisite two-story retreat on Kent Island, designed to captivate with its modern allure and exclusive fe ...
From $295 per night (USD)VRBO
- Click For Pricing
Expedia
Historic downtown Chestertown Home. #1 Location.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Your family and guests will experience the best of Chestertown in this family friendly and historic home. 2 Blocks from ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $361 per night (USD)
Expedia
Chester River Waterfront Cottage (Love Point Bay)
- 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 $361 per night (USD)Expedia
- From $699 per night (USD)
VRBO
Love Point Luxury Waterfront
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $699 per night (USD)VRBO
- From $843 per night (USD)
Expedia
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open fl ...
From $843 per night (USD)Expedia
- 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 $800 per night (USD)
VRBO
Historic Stepne Manor on Maryland's Eastern Shore
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Accommodations: Manor House - Five Bedrooms (including one Private Suite), three and one-half Baths, Sitting Room, Den, ...
From $800 per night (USD)VRBO
- From $144 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 $144 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
- 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 $850 per night (USD)
Expedia
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 $850 per night (USD)Expedia
- From $217 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 $217 per night (USD)VRBO
- 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 $281 per night (USD)
VRBO
Newly restored apartment in the heart of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of al ...
From $281 per night (USD)VRBO
- From $143 per night (USD)
VRBO
2 Beds, 2.5 Baths, Perfect Downtown Location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accom ...
From $143 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 $1100 per night (USD)
Expedia
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)Expedia
- From $489 per night (USD)
VRBO
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)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 $750 per night (USD)
VRBO
Great waterfront house in Grasonville
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Modern Contemporary waterfront house with grand kitchen open floor plan 3 levels overlooking Bay on Eastern shore just m ...
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 $550 per night (USD)
VRBO
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Sky View. The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is cre ...
From $550 per night (USD)VRBO
- From $161 per night (USD)
Expedia
Historic Downtown Garden Oasis with Private Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $161 per night (USD)Expedia
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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 $225 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 $225 per night (USD)VRBO
- 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 $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 $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)
VRBO
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)VRBO
- 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 $596 per night (USD)
VRBO
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 $596 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 $1056 per night (USD)
Expedia
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 $1056 per night (USD)Expedia