Queen Anne's Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Queen Anne's Area, Maryland on RentalSaver.com!

Queen Anne's Area Rentals

From $303 per night (USD)
VRBO
Relax on Kent Island in 3 Bedroom Home w/Waterview
Bedrooms:
2
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 $303 per night (USD)
VRBO
From $1253 per night (USD)
Expedia
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Bedrooms:
6
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 $1253 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Second Floor Bed and Bath in Stevensville, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Second floor bed and bath with private entrance, dedicated HVAC, and balcony overlooking the backyard, located in Chesap ...
From $168 per night (USD)
VRBO
From $152 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 $152 per night (USD)
VRBO
From $522 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 $522 per night (USD)
VRBO
From $922 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 $922 per night (USD)
Expedia
From $347 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 $347 per night (USD)
VRBO
From $333 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 3+ Bedroom Home with 3 acres of outdoor living! Perfect for Families ...
From $333 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Country Estate in Historic District
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $389 per night (USD)
VRBO
From $1920 per night (USD)
Expedia
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, ...
From $1920 per night (USD)
Expedia
From $159 per night (USD)
VRBO
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 $159 per night (USD)
VRBO
From $555 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 $555 per night (USD)
VRBO
From $706 per night (USD)
VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $706 per night (USD)
VRBO
From $547 per night (USD)
Expedia
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Kent Island Chesapeake Bay Cottage with Private Pool & Sunset Views Welcome to your dreamy poolside getaway! This charm ...
From $547 per night (USD)
Expedia
From $365 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 $365 per night (USD)
VRBO
From $156 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 $156 per night (USD)
VRBO
From $450 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 $450 per night (USD)
VRBO
From $325 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 $325 per night (USD)
Expedia
From $450 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 $450 per night (USD)
VRBO
From $238 per night (USD)
Expedia
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 $238 per night (USD)
Expedia
From $830 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 $830 per night (USD)
VRBO
From $654 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 $654 per night (USD)
VRBO
From $749 per night (USD)
VRBO
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Bedrooms:
5
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 $749 per night (USD)
VRBO
From $1092 per night (USD)
Expedia
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 $1092 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Bedrooms:
2
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 $444 per night (USD)
VRBO
From $963 per night (USD)
Expedia
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 $963 per night (USD)
Expedia
From $463 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 $463 per night (USD)
VRBO
From $527 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 $527 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
Chesapeake Bay Waterfront ARTectural Home
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can i ...
From $1086 per night (USD)
VRBO
Click For Pricing
Expedia
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore
Bedrooms:
4
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 Pricing
Expedia
From $595 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 $595 per night (USD)
VRBO
From $191 per night (USD)
Expedia
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 $191 per night (USD)
Expedia
From $788 per night (USD)
VRBO
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Working Farm on Reeds Creek This lovely working farm is on a peninsula situated between Grove Creek and (surely not to ...
From $788 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining ...
From $546 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $856 per night (USD)
Expedia
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
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 $856 per night (USD)
Expedia
Click For Pricing
VRBO
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
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, ...
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VRBO
From $550 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 $550 per night (USD)
Expedia
From $1474 per night (USD)
VRBO
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 8-10-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 $1474 per night (USD)
VRBO
From $876 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 $876 per night (USD)
Expedia
From $562 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 $562 per night (USD)
VRBO
From $901 per night (USD)
Expedia
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
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 $901 per night (USD)
Expedia
From $561 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 $561 per night (USD)
VRBO
From $170 per night (USD)
VRBO
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 $170 per night (USD)
VRBO
From $662 per night (USD)
VRBO
Kent Island Waterfront | Game Room | 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 $662 per night (USD)
VRBO
From $221 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 $221 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Away at the Bay: New Home on the Chesapeake Bay!
Bedrooms:
4
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 $587 per night (USD)
VRBO
From $329 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 $329 per night (USD)
Expedia
From $745 per night (USD)
VRBO
Breathtaking waterfront home on the Chester River
Bedrooms:
4
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 $745 per night (USD)
VRBO
From $592 per night (USD)
Expedia
Private pier at multi-suite waterfront home on the Bay 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 $592 per night (USD)
Expedia
Click For Pricing
VRBO
Kent Island - Gorgeous Waterfront Home
Bedrooms:
2
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 Pricing
VRBO
From $370 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 $370 per night (USD)
Expedia
From $804 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 $804 per night (USD)
VRBO
From $865 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 $865 per night (USD)
Expedia
From $413 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 $413 per night (USD)
VRBO
From $586 per night (USD)
Expedia
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Bedrooms:
3
Bathrooms:
5
Sleeps:
25
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $586 per night (USD)
Expedia
From $216 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 $216 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 Pricing
Expedia
From $1323 per night (USD)
VRBO
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Experience the ultimate getaway at this gorgeous Kent Island waterfront! This 4,600 square-foot, 6-bedroom, 4.5-bathroo ...
From $1323 per night (USD)
VRBO
From $192 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 $192 per night (USD)
Expedia
From $1625 per night (USD)
VRBO
The Colonial Farmhouse
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 $1625 per night (USD)
VRBO
From $298 per night (USD)
Expedia
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 $298 per night (USD)
Expedia
From $959 per night (USD)
VRBO
Waterfront Estate w Private Pier, Game Room & Bar
Bedrooms:
3
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 $959 per night (USD)
VRBO
From $1242 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 $1242 per night (USD)
Expedia
Click For Pricing
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 ...
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VRBO
From $824 per night (USD)
Expedia
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 $824 per night (USD)
Expedia
From $825 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 $825 per night (USD)
VRBO
Click For Pricing
Expedia
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vacation With No Limits! The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is created by a sprawling inte ...
Click For Pricing
Expedia
From $193 per night (USD)
VRBO
Historic Downtown Garden Oasis with Private Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $193 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $193 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 $193 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Lansdowne Manor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Historic country manor located in a private tranquil setting, surrounded by mature trees & nature. ★ "An absolutely ama ...
From $288 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing
Bedrooms:
4
Bathrooms:
3
Sleeps:
9
Enjoy waterfront views of Cox Creek from this stunning custom home on Maryland’s Eastern Shore. With its private pier, e ...
From $705 per night (USD)
VRBO
From $473 per night (USD)
Expedia
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 $473 per night (USD)
Expedia
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 Pricing
VRBO
From $1328 per night (USD)
VRBO
Paradise on Kent Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
PLEASE NOTE: If you request to book this property, you will be contacted by Annapolis Accommodations to finalize your ...
From $1328 per night (USD)
VRBO
From $575 per night (USD)
VRBO
family friendly nice quiet neighborhood close to most major cities
Bedrooms:
2
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 $575 per night (USD)
VRBO
From $912 per night (USD)
Expedia
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Winchester Creek Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $912 per night (USD)
Expedia
From $450 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 $450 per night (USD)
VRBO
From $456 per night (USD)
Expedia
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. W ...
From $456 per night (USD)
Expedia
Click For Pricing
VRBO
Belle Blu of Kent Narrows Grasonville, Maryland
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
<p>You'll find bicycles on site at this family-friendly apartment. With convenient onsite parking, you'll be ready to ma ...
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VRBO
From $84 per night (USD)
Expedia
Cozy Waterfront Apartment Chester, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*We live on the property* NO SMOKING OF ANY KIND is permitted in this apartment or on the property whatsoever. The apar ...
From $84 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our brand-new coastal cottage, a haven for your perfect getaway in a community that offers 3 different locati ...
From $524 per night (USD)
VRBO
From $502 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 $502 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Waterfront Millington Vacation Rental w/ Hot Tub!
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...
From $517 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 Pricing
Expedia
From $245 per night (USD)
VRBO
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the vi ...
From $245 per night (USD)
VRBO
From $1090 per night (USD)
VRBO
Incredible home with Panoramic Chesapeake Bay view
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Experience unforgettable Chesapeake Bay living. The lighthouse views at night, the panoramic bay vistas, and the charm o ...
From $1090 per night (USD)
VRBO
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You can explore the Eastern Shore's cuisine within a 5 minute drive to Kent Narrows. Enjoy a relaxing fishing trip with ...
From $263 per night (USD)
Expedia
From $768 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 $768 per night (USD)
VRBO
From $534 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 $534 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Waterfront Sunset Bayview: sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent dir ...
From $455 per night (USD)
VRBO
From $85 per night (USD)
Expedia
Guest Suite for up to 2 in a Victorian on the Chester River
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liq ...
From $85 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Bedrooms:
2
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 $226 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Gorgeous Creek Side Ranch-Style Estate With Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Summary: Welcome to our Chesapeake Oasis! Quiet Queenstown is a beautiful and historic part of Maryland's Eastern Shore ...
From $667 per night (USD)
Expedia
From $375 per night (USD)
VRBO
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 $375 per night (USD)
VRBO
From $333 per night (USD)
Expedia
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 $333 per night (USD)
Expedia
From $1269 per night (USD)
VRBO
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 $1269 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Peaceful Queenstown Home w/ Deck & Grill!
Bedrooms:
2
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 $347 per night (USD)
VRBO

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Results: 143 Rentals