Miles River Rentals
- From $850 per night (USD)
VRBO
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go ...
From $850 per night (USD)VRBO
- From $491 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 $491 per night (USD)Expedia
- From $736 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Leeds Landing. Situated on a quiet 2+acre waterfront lot, this home is perfect f ...
From $736 per night (USD)VRBO
- 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 $900 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License STRN-22-36 This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was designed with your co ...
From $900 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W\/ HEATED POOL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
STRN-22-40 Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of ...
From $1000 per night (USD)VRBO
- From $733 per night (USD)
VRBO
Trend Setting Waterfront St. Michaels - Feb bookings include wine & roses
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD Short Term Rental License #STRN-23-12 located in the Hamlet of Royal Oak central to nearby visitor si ...
From $733 per night (USD)VRBO
- From $375 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 $375 per night (USD)Expedia
- From $383 per night (USD)
VRBO
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 $383 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 $2500 per night (USD)
VRBO
Waterfront-Private 153 acre Historic Estate
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 12
We open our gates and invite you in to the very exclusive, one of a kind experience at historic Langdon Estate. This pre ...
From $2500 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Waterfront Estate. **WALK TO ST. MICHAELS!**
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Ship's Cove!! This three acre estate is your private oasis for the duration of your stay. Make some memories ...
From $1500 per night (USD)Expedia
- From $492 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 $492 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $323 per night (USD)Expedia
- From $387 per night (USD)
VRBO
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 $387 per night (USD)VRBO
- From $552 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 $552 per night (USD)Expedia
- From $508 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 $508 per night (USD)VRBO
- From $717 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 $717 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Dollhouse in Central Historic St Michaels
- Bedrooms:
- 2
- 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 $265 per night (USD)VRBO
- From $636 per night (USD)
Expedia
Downtown St. Michaels | Bikes | Kayaks | Private Pier
- Bedrooms:
- 3
- 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 $636 per night (USD)Expedia
- From $808 per night (USD)
VRBO
Picturesque Panoramic View of Kentmorr Marina, Fishing Boats & Beach Bar & Grill
- 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 $808 per night (USD)VRBO
- From $935 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 $935 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 $1166 per night (USD)
Expedia
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 $1166 per night (USD)Expedia
- From $478 per night (USD)
VRBO
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated and newly furnished, this lovely in-town cottage is close to all the amenities and charms of historic ...
From $478 per night (USD)VRBO
- From $356 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 $356 per night (USD)Expedia
- From $850 per night (USD)
VRBO
HUGE SANDBOX! Play Beach Volleyball by the 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 $850 per night (USD)VRBO
- From $1217 per night (USD)
Expedia
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License #ST-102-WEI Located just on the outskirts of St. Michaels, this fantastic family vacation com ...
From $1217 per night (USD)Expedia
- From $317 per night (USD)
VRBO
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
- Bedrooms:
- 3
- 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 $317 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Hot Tub | Private Dock | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sprawling Cottage with Hot Tub Under the Stars and Gorgeous Sunsets Over the Water A taste of paradise on the Chesapeake ...
From $351 per night (USD)Expedia
- From $336 per night (USD)
VRBO
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $336 per night (USD)VRBO
- From $550 per night (USD)
Expedia
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 $550 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Walk to Everything House
- Bedrooms:
- 2
- 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 $334 per night (USD)VRBO
- From $710 per night (USD)
Expedia
Waterfront Property, kayaks, private dock, near town
- Bedrooms:
- 3
- 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 $710 per night (USD)Expedia
- From $625 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 $625 per night (USD)VRBO
- From $251 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 $251 per night (USD)Expedia
- From $768 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 $768 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 $895 per night (USD)
VRBO
Historic Elegance and Modern Luxury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This three bedroom, three bathroom cottage offers an exclusive escape, combining comfort and modern luxuries. I ...
From $895 per night (USD)VRBO
- From $1199 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 $1199 per night (USD)VRBO
- 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 $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 $450 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 $450 per night (USD)VRBO
- From $400 per night (USD)
VRBO
BOOK NOW FOR FALL & WINTER DATES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STN-22-40 ONE OF OUR MOST SOUGHT AFTER PROPERTIES! MINUTES FROM ST. MICHAELS...... Peaceful retreat with breathtaking su ...
From $400 per night (USD)VRBO
- From $457 per night (USD)
VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated one story home directly on the water. Gorgeous hickory floors. Open layout for entertaining. Din ...
From $457 per night (USD)VRBO
- From $337 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 $337 per night (USD)VRBO
- From $610 per night (USD)
VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
- Bedrooms:
- 4
- 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 $610 per night (USD)VRBO
- From $295 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 $295 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 $790 per night (USD)
VRBO
Beautiful, 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 $790 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 $475 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 $475 per night (USD)VRBO
- From $745 per night (USD)
VRBO
🦆Tuckaway Cove🦆 Private, relaxing waterfront property; close to everything!
- 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 $745 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
SEPT SUMMERS & FREE BUSHEL OF CRABS W\/SEPT\/OCT BOOKING
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD License #STRN-23-16 - The Cove At St. Michaels is a magnificent 15.5 acre estate property with ingrou ...
From $1200 per night (USD)Expedia
- From $1350 per night (USD)
VRBO
Classic Eastern Shore Waterfront Manor House - ST-936
- Bedrooms:
- 5
- 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 $1350 per night (USD)VRBO
- From $1409 per night (USD)
VRBO
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
TALBOT COUNTY SHORT-TERM RENTAL LICENSE: ST-895-REH 2019 10 Person Maximum PEAK SEASON BOOKINGS ARE 7 DAY OR MORE BOOK ...
From $1409 per night (USD)VRBO
- From $565 per night (USD)
VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-22 Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Easte ...
From $565 per night (USD)VRBO
- From $660 per night (USD)
VRBO
St. Michael's Premier In-Town Rental with heated pool - Pool opens 4\/12\/24
- 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 $660 per night (USD)VRBO
- From $1028 per night (USD)
VRBO
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
All persons thinking about making a booking, should consider adding travel cancellation insurance, prior to booking. Th ...
From $1028 per night (USD)VRBO
- From $404 per night (USD)
VRBO
BOOKING FALL & WINTER-ACT NOW FOR BEST AVAILABILITY!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-HARG Within minutes of historic St Michaels this 4 BEDROOM waterfront home is located on Tilghman Island. A wat ...
From $404 per night (USD)VRBO
- From $575 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 $575 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- From $2817 per night (USD)
VRBO
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT\/30 ACRES\/HUGE POLYWOOD PLAYGROUND
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $2817 per night (USD)VRBO
- From $967 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 $967 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
- From $1141 per night (USD)
VRBO
A Waterfront Escape Like No Other
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: The Farm at Bald Eagle Point is the great escape! Our guests can settle in and never have to leave this exclusi ...
From $1141 per night (USD)VRBO
- From $481 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 $481 per night (USD)VRBO
- From $841 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment ...
From $841 per night (USD)Expedia
- From $1149 per night (USD)
VRBO
Heated pool, sandy beach, pier, and playground set punch point apart!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
TREMEZZO STAY - PUNCH POINT Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury re ...
From $1149 per night (USD)VRBO
- From $520 per night (USD)
Expedia
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 $520 per night (USD)Expedia
- 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
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 $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 $275 per night (USD)
VRBO
Quaint Tilghman Island home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Vacation home minutes from St Michaels. Tucked away on a quiet neighborhood street is the Wandering Loon. A pe ...
From $275 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Warmth and Comfort Await
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Step into a thoughtfully curated space where coastal decor meets serene comfort. The open-concept living area i ...
From $295 per night (USD)VRBO
- Click For Pricing
Expedia
Your “Happy Place”-Updated beautifully 3 story home on quiet island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local se ...
Click For PricingExpedia
- From $415 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 $415 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 ...
Click For PricingExpedia
- From $140 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 $140 per night (USD)VRBO
- From $555 per night (USD)
Expedia
Grace Cottage, Saint Michaels Walk to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
About this space Welcome to Grace Street Cottage in the heart of Saint Michaels. Walk to shops, restaurants and experien ...
From $555 per night (USD)Expedia
- From $722 per night (USD)
VRBO
Unwind at this Waterfront Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This beautiful home is minutes from historic St Michaels. Enjoy your morning coffee on the covered deck. Days c ...
From $722 per night (USD)VRBO
- From $703 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents Crew's Quarters. Step into this idyllic, uniquely Eastern Shore Nanticoke mid- c ...
From $703 per night (USD)Expedia
- From $688 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Eastern Shore Vacation Rentals presents Quailsar Farm. The impressive 5BR, 3.5BA vacation estate with a free-flowing flo ...
From $688 per night (USD)VRBO
- From $750 per night (USD)
Expedia
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)Expedia
- From $695 per night (USD)
VRBO
Eastern Shore Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Miles Away is a beautifully renovated 4 bedroom waterfront rancher with luxurious pool, wrap around deck and screened-in ...
From $695 per night (USD)VRBO
- From $1190 per night (USD)
VRBO
ST MICHAELS-Private Waterfront,Dock, Huge Deck&Heated 19’Swim spa-pool 2 MBRooms
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
1 Mile to St Michaels-THE ST MICHAELS HARBOR SHUTTLE CAN PICK YOU UP AT OUR DOCK or WALK/BIKE/KAYAK TO ST MICHAELS, WE A ...
From $1190 per night (USD)VRBO
- From $481 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Kayaks | Stunning Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STN-22-29 Truly exceptional 4-bedroom, 2-bathroom Leeds Creek waterfront, the open floor plan ...
From $481 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Modern Studio in heart of town.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Let us know if you'd like a bottle of your favorite wine and charcuterie upon arrival. Its the perfect start to ...
From $250 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Discover Your Perfect Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: We've put extra care into creating a welcoming atmosphere for you to relax and make the most of your time in th ...
From $425 per night (USD)VRBO
- From $534 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 $534 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 $150 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 $150 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Fabulous in town luxury studio
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Located in the heart of historic St Michaels, this unique studio has a style all its own. Award winning restau ...
From $350 per night (USD)VRBO
- From $289 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 $289 per night (USD)VRBO
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Expedia
Cottage downtown on a quiet street
- Bedrooms:
- 2
- 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 ...
Click For PricingExpedia
- 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 $432 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License #ST-803-HOO This 3-bedroom, 2.5-bathroom shingle style cottage offers a character-filled inte ...
From $432 per night (USD)VRBO
- From $757 per night (USD)
VRBO
Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County ST Rental License: ST-785-WAT New 2022 Listing! 8 Persons Maximum PEAK SEASON BOOKINGS ARE 7 DAY OR MORE ...
From $757 per night (USD)VRBO
- From $675 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 $675 per night (USD)VRBO
- From $1264 per night (USD)
Expedia
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
Talbot County STR License STRN-23-10 This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a spa-l ...
From $1264 per night (USD)Expedia