Miles River, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Miles River, Maryland on RentalSaver.com!

Miles River Rentals

From $1280 per night (USD)
VRBO
Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings **IMPORTA ...
From $1280 per night (USD)
VRBO
From $606 per night (USD)
VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
STRN-23-22 BOOK WITH US AND RECEIVE A FREE BUSCHEL OF CRABS! Come enjoy the quaintness of Claiborne, MD, just 5 minutes ...
From $606 per night (USD)
VRBO
From $766 per night (USD)
VRBO
St. Michael's Premier In-Town Rental with heated pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
As Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. H ...
From $766 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 $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 $504 per night (USD)
VRBO
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
ST-605-JOH Upon arrival you realize this is the Eastern Shore Experience you have been looking for......A gated garden ...
From $504 per night (USD)
VRBO
From $825 per night (USD)
VRBO
Tuckaway Cove. Book your fall get away now. New kitchen 2025
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Tucked away on a beautiful, quiet cove off the Miles River, with a large yard for playing, a private pool & dock, & kaya ...
From $825 per night (USD)
VRBO
$ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY$
From $1406 per night (USD)
Expedia
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Talbot County MD License #STRN-24-89 - The Cove At St. Michaels is a magnificent 15.5 acre estate property with ingrou ...
From $1406 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Classic Eastern Shore Waterfront Manor House - ST-936
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Quintessential Eastern Shore experience on 30 acres 1.5 miles from downtown St. Michaels. Original house dates to the e ...
From $1535 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 $347 per night (USD)
VRBO
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore esca ...
From $347 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Bedrooms:
3
Bathrooms:
6
Sleeps:
9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $693 per night (USD)
VRBO
From $302 per night (USD)
VRBO
Stay in the HEART of Saint Michaels!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, resta ...
From $302 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 $885 per night (USD)
VRBO
Private Retreat with HUGE Water Views!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Wonderful large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), th ...
From $885 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $363 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated one story home directly on the water. Gorgeous hickory floors. Open layout for entertaining. Din ...
From $532 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 $407 per night (USD)
Expedia
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The house is a 2 bedroom 2 ...
From $407 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 $854 per night (USD)
Expedia
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Talbot County MD Short Term Rental License #STRN-23-12 Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5- ...
From $854 per night (USD)
Expedia
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 $872 per night (USD)
Expedia
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
All persons thinking about making a newbooking, should consider adding travel cancellation insurance, prior to booking. ...
From $872 per night (USD)
Expedia
From $1144 per night (USD)
VRBO
Thorneton Point Estate
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: **HEATABLE SPA** Nestled on the tip of an idyllic private 5 acre peninsula, minutes from historic St. Michaels, ...
From $1144 per night (USD)
VRBO
From $444 per night (USD)
Expedia
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)
Expedia
From $753 per night (USD)
VRBO
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Escape to our 4-bedroom vacation home in Easton, just a 5-7 minute drive from the renowned St. Michaels. Immerse yoursel ...
From $753 per night (USD)
VRBO
From $1503 per night (USD)
Expedia
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Bedrooms:
9
Bathrooms:
8
Sleeps:
12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $1503 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 $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
From $191 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 $191 per night (USD)
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
From $1523 per night (USD)
VRBO
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fanta ...
From $1523 per night (USD)
VRBO
From $1004 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was d ...
From $1004 per night (USD)
Expedia
From $550 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 $550 per night (USD)
VRBO
From $1474 per night (USD)
Expedia
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)
Expedia
From $876 per night (USD)
VRBO
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)
VRBO
From $1708 per night (USD)
Expedia
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Looking to getaway, relax and recharge? This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a sp ...
From $1708 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Charming Waterfront Cottage Within Minutes to Historic St. Michaels. Kayaks and Bikes Included! Comfortably furnished an ...
From $654 per night (USD)
VRBO
From $694 per night (USD)
Expedia
Tilghman | Pool | Private Dock | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Talbot County STR License# STRN-22-1 Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and ...
From $694 per night (USD)
Expedia
From $1192 per night (USD)
VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of luxury acco ...
From $1192 per night (USD)
VRBO
From $752 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great location with plenty of room for friends and family. Wonderful outdoor spaces to enjoy! This little gem on the ban ...
From $752 per night (USD)
Expedia
From $453 per night (USD)
VRBO
BOOK NOW FOR SPRING & SUMMER DATES.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STN-22-40 ONE OF OUR MOST SOUGHT AFTER PROPERTIES! MINUTES FROM ST. MICHAELS...... Peaceful retreat with breathtaking su ...
From $453 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
An oasis of peace and relaxation! This 3-bedroom, 2.5-bathroom shingle style cottage offers a character-filled interior ...
From $585 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Dollhouse in Central Historic St Michaels
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The ho ...
From $295 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Waterfront Cottage in St Michaels Begin your day at Riverview Retreat with a beautiful sunrise and be amazed wi ...
From $759 per night (USD)
Expedia
From $901 per night (USD)
VRBO
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)
VRBO
From $661 per night (USD)
Expedia
St. Michaels Waterfront Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful waterfront home sits just over the bridge entering St. Michaels in a prime location. Breathtaking waterf ...
From $661 per night (USD)
Expedia
From $363 per night (USD)
VRBO
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $363 per night (USD)
VRBO
From $662 per night (USD)
Expedia
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)
Expedia
From $297 per night (USD)
VRBO
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the h ...
From $297 per night (USD)
VRBO
From $1113 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Hot Tub, Pool and Cabana House … Oh My! Built in 1930, this 5-bedroom, 3.5-bathroom waterfront getaway sits on 2.2 acre ...
From $1113 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $330 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 $1154 per night (USD)
VRBO
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Ingleton! EARLY CHECKIN AND LATECHECKOUT OCTOBER. Relax by the pool. Fish or crab or picnic at the end of t ...
From $1154 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Waterfront, 2 bedroom, 2 bath Private Cottage on Solitude Creek. 3.4 miles to St. Michaels and Oxford; 1 1/2 hours to O ...
From $391 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Walk to Everything House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The historic house which was restored from 2016-2020, is conveniently located on a quiet street near the Blue Crab coffe ...
From $353 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Cottage downtown on a quiet street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In search of a cottage in downtown St. Michaels for a nice weekend? Located on a quiet street, yet steps away from shopp ...
From $296 per night (USD)
Expedia
From $694 per night (USD)
VRBO
Waterfront Property, kayaks, private dock, near town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginnin ...
From $694 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
From $995 per night (USD)
VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $995 per night (USD)
VRBO
Click For Pricing
Expedia
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
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 $322 per night (USD)
VRBO
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for an Eastern Shore waterfront retreat that's perfect for a romantic long weekend, a family vacation with the k ...
From $322 per night (USD)
VRBO
Click For Pricing
VRBO
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
VRBO
From $1323 per night (USD)
Expedia
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)
Expedia
From $451 per night (USD)
VRBO
Tilghman | Fenced Yard | Pet Friendly | Charming
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Talbot County STR License #STN-22-20 This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-f ...
From $451 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Harbor View Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including th ...
From $241 per night (USD)
Expedia
From $836 per night (USD)
VRBO
Eastern Shore Oasis!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Miles Away is a beautifully renovated 4 bedroom waterfront rancher with luxurious pool, wrap around deck and screened-in ...
From $836 per night (USD)
VRBO
From $1355 per night (USD)
VRBO
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS MAY 26-30,JULY 16-19 and JULY 27-8/2 Fantastic ...
From $1355 per night (USD)
VRBO
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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 $996 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Toto, There’s No Place Like This Vacation Home! The impressive 5BR, 3.5BA vacation estate with a free-flowing floor pla ...
From $996 per night (USD)
Expedia
From $824 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 $824 per night (USD)
VRBO
From $825 per night (USD)
Expedia
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)
Expedia
From $982 per night (USD)
VRBO
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: Discover the ultimate Eastern Shore escape at The Farm at Bald Eagle Point—a private 6-bedroom waterfront estat ...
From $982 per night (USD)
VRBO
From $307 per night (USD)
Expedia
4-Bedroom Retreat: Modern, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Heart of the Island & Pet Friendly Retreat on Tilghman Island! Step into a thoughtfully curated space where coa ...
From $307 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This newly renovated 3BR, 3BA Sherwood vacation home is designed with your comfort in mind. The free-flowing floor plan ...
From $491 per night (USD)
VRBO
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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 ...
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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 $300 per night (USD)
VRBO
Romantic Waterfront Cottage with Amazing Sunsets
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located on the Chesapeake Bay side of Tilghman Island, our beautiful property is host to several cottages (one, two and ...
From $300 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Stay steps from Saint Michaels’ best shops, dining, and waterfront views! This stylish studio blends historic c ...
From $286 per night (USD)
VRBO
From $705 per night (USD)
Expedia
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)
Expedia
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VRBO
Seasonal Rental: Artisan designed 3 bedroom home.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kick back and relax St Michaels' style in this seasonal rental. This area of St Michaels requires a 4 month minimum stay ...
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VRBO
From $1016 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A Perfect Single-Story Waterfront Retreat! Situated on a quiet 2+acre waterfront lot, this home is perfect for active f ...
From $1016 per night (USD)
Expedia
From $620 per night (USD)
VRBO
St. Michaels Escape | Pool, Hot Tub & Fire Pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. ...
From $620 per night (USD)
VRBO
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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 ...
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Expedia
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 $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 $163 per night (USD)
VRBO
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The village of Sherwood is located on Harris Creek. The cottage, at 21902 Sherwood Landing Rd., is a perfect place to r ...
From $163 per night (USD)
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 $390 per night (USD)
VRBO
Downtown Retreat with Bikes, Fire Pit & Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Just minutes from downtown St. Michaels, this stylish 2-bedroom retreat combines modern design with thoughtful ...
From $390 per night (USD)
VRBO
From $524 per night (USD)
Expedia
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)
Expedia
From $502 per night (USD)
VRBO
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)
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 $261 per night (USD)
Expedia
15% Off Promo! Tilghman Cottage by Views & Eats
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: This isn’t just a place to stay. It’s a place to pause. To breathe. To remember what it feels like to just be. ...
From $261 per night (USD)
Expedia
$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$
From $334 per night (USD)
VRBO
\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Tilghman Island “Point of View” is a waterfront property located on Tilghman Island, with a 270-degree water view ov ...
From $334 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This m ...
From $820 per night (USD)
Expedia
From $708 per night (USD)
VRBO
Ferry Bridge House
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Ferry Bridge House is a hidden gem that feels a world away from everyday life. This property is secluded but just a shor ...
From $708 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Very cosy and nicely appointed Waterfront Cottage with gorgeous views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
License # STRN-24-69...A long, driveway leads to this updated and charming 1930's St. Michaels Cottage situated on two a ...
From $523 per night (USD)
VRBO

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