Talbot Area Rentals
From $250 per night (USD)VRBO
Charming Saint Michaels home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This charming 3-bedroom, 2-bath rancher is conveniently located in Historic St. Michaels. Just a short stroll to the Bac ...
From $250 per night (USD)VRBO
From $919 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 $919 per night (USD)VRBO
From $568 per night (USD)VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
ST-104-LED Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Easte ...
From $568 per night (USD)VRBO
From $490 per night (USD)VRBO
Waterfront Home with Magnificent Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
A converted barn house with updated finishes is the perfect spot for your vacation on the Eastern Shore of the Chesapeak ...
From $490 per night (USD)VRBO
From $960 per night (USD)VRBO
Historic Oxford Waterfront Estate
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Bonfield Manor is located at the entrance of Oxford, a half-mile walk or bike ride to restaurants, shops and the Rivervi ...
From $960 per night (USD)VRBO
From $924 per night (USD)VRBO
St. Michael's Premier In-Town Rental with heated pool and 2023 Designer updates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Could HH get any better? We never stop trying to earn our title as a 'Premier Property'! We take this title very seriou ...
From $924 per night (USD)VRBO
From $737 per night (USD)VRBO
Waterfront, Pool, Dock, Stunning Views! Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
License No. ST-575-PRO Summer 7 Night Minimum Deep water dock will accommodate a 52' yacht! Catch fresh fish and g ...
From $737 per night (USD)VRBO
From $400 per night (USD)VRBO
FALL ESCAPE - Private Residence on Harris Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This Farmhouse was built nearby and lifted onto it's foundation by field workers. The property was once home to Speaker ...
From $400 per night (USD)VRBO
From $300 per night (USD)VRBO
Eastern Shore Getaway Near St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
PERFECT COUPLE'S GET AWAY OR WRiTERS RETREAT! Dogs welcome to enjoy the private waterfront getaway on sixteen acres with ...
From $300 per night (USD)VRBO
From $355 per night (USD)Expedia
Algonquin on the Choptank River is a great getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The house is on the Choptank River with awesome views, a pier with boat lift, great fishing and water activities. The h ...
From $355 per night (USD)Expedia
From $861 per night (USD)VRBO
Holly Harbor Court - Waterfront Perfection!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This charming 4-bedroom, 4-bathroom historic shore house sits on 4+ acres with 450+ ft of waterfront. The free-flowing f ...
From $861 per night (USD)VRBO
From $345 per night (USD)Expedia
The Middle Point Cabin in Saint Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Our Talbot County Short Term Rental License Number is: ST-634-EIN 2019 Talbot County requires a minimum 3 night booking ...
From $345 per night (USD)Expedia
From $375 per night (USD)VRBO
Cottage at Goose Neck Point
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming newly renovated cottage at the end of a private drive. Direct access to the Tred Avon River. Spectacular view ...
From $375 per night (USD)VRBO
From $1748 per night (USD)Expedia
Jewel of the Tred Avon - Shore Royalty!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License STRN-23-7 This 7,700 sq ft magnificently renovated nantucket style coastal home offers 5 BR, ...
From $1748 per night (USD)Expedia
From $498 per night (USD)VRBO
Beautiful Colonial Home on the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this newly updated 4-bedroom, 2-bath colonial home for a fun-filled retreat on the Cambridge coast! Offering k ...
From $498 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 $666 per night (USD)VRBO
Thorntonwood - Family Fun on Broad Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STRN-22-6 Thorntonwood offers a plethora of opportunities for indoor and outdoor fun! The hom ...
From $666 per night (USD)VRBO
From $620 per night (USD)VRBO
Book now for your fall stay
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: STRN-22-23 Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacati ...
From $620 per night (USD)VRBO
From $427 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 $427 per night (USD)VRBO
From $650 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 $650 per night (USD)VRBO
From $1200 per night (USD)VRBO
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)VRBO
From $1357 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 $1357 per night (USD)VRBO
From $327 per night (USD)VRBO
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Less than a half mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore ...
From $327 per night (USD)VRBO
From $750 per night (USD)Expedia
Indian Fields - 25-Acre Nature Lovers retreat!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Indian Fields - Twenty-five acre nature lovers retreat! Pool, Kayaks, Fire Pit - The family Dog is Welcome! Bring your ...
From $750 per night (USD)Expedia
From $690 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 $690 per night (USD)VRBO
From $250 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 $250 per night (USD)VRBO
From $767 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 $767 per night (USD)VRBO
From $591 per night (USD)VRBO
Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Master Bed room has 1 king size bed. Bedroom 1 has 1 queen and 2 single, and bedroom 2 is located in the 3 floor off the ...
From $591 per night (USD)VRBO
From $341 per night (USD)VRBO
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 $341 per night (USD)VRBO
From $250 per night (USD)VRBO
Cottage on Cabin Creek
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The cottage is the perfect place for a couple's get away. The views of Cabin Creek are stunning. You will enjoy beautifu ...
From $250 per night (USD)VRBO
From $986 per night (USD)VRBO
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Talbot County rental license ST-644-LYT Over the years we have had so many guests inquire about the Royal Oak area. Ou ...
From $986 per night (USD)VRBO
From $816 per night (USD)VRBO
Luxury Waterfront Near St Michaels/Easton
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
License # STRN-22-17 Summer 7 Night Minimum "Sunset's Edge" delivers stunning views, water access, relax ...
From $816 per night (USD)VRBO
From $722 per night (USD)VRBO
Beautiful Waterfront Home w/ Pool In St. Michaels
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful house with spectacular views from almost every room. Location is a couple of miles from the center of St. Mich ...
From $722 per night (USD)VRBO
From $375 per night (USD)VRBO
Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, three bedroom cottage is available for ...
From $375 per night (USD)VRBO
From $500 per night (USD)VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Contact us for other pricing options and special rates. Beautifully renovated one story home directly on the water. Gor ...
From $500 per night (USD)VRBO
From $1395 per night (USD)Expedia
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Licensed by Talbot Co MD STRN-23-11. Mimimum 7 night reservations only - Sat to Sat. Our property is ideally suited for ...
From $1395 per night (USD)Expedia
Click For PricingVRBO
St. Michaels Area Cottage - Walk to Water & Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental ...
Click For PricingVRBO
From $381 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 $381 per night (USD)Expedia
From $550 per night (USD)VRBO
Heron There of Royal Oak
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License #ST-258-GRE This 4-bedroom, 3-bathroom waterfront retreat on Plaindealing Creek in Royal Oak ...
From $550 per night (USD)VRBO
From $386 per night (USD)Expedia
Historic Renovated Jackrabbit Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $386 per night (USD)Expedia
From $275 per night (USD)VRBO
Time to book for summer.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: ST-215-DON Located on a Island with the waters of the Chesapeake on one side & Harris Creek on the other. Tilg ...
From $275 per night (USD)VRBO
From $593 per night (USD)VRBO
Trend Setting Waterfront minutes to St. Michaels -
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD Short Term Rental License #STRN-23-12 You will arrive at your destination to find a beautiful 4000+sq ...
From $593 per night (USD)VRBO
From $393 per night (USD)VRBO
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
5 Bedroom, 3.5 Bath, Pool, Dock Private Retreat. Welcome to Travelers Rest! A quiet and secluded neighborhood true to ...
From $393 per night (USD)VRBO
From $2500 per night (USD)Expedia
Waterfront-Private 153 acre Historic Estate
- Bedrooms:
- 7
- Bathrooms:
- 10
- 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)Expedia
From $720 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 $720 per night (USD)VRBO
From $414 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 $414 per night (USD)VRBO
From $1180 per night (USD)VRBO
Thorneton Point Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: *Pool now open for the 2023 season!* Nestled on the tip of an idyllic private 5 acre peninsula, minutes from hi ...
From $1180 per night (USD)VRBO
From $1248 per night (USD)VRBO
Breathtaking Waterfront Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: *Pool now open for the 2023 season!* Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with it ...
From $1248 per night (USD)VRBO
From $458 per night (USD)VRBO
House on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $458 per night (USD)VRBO
From $763 per night (USD)Expedia
Beautiful Waterfront Home with POOL minutes from St. Michaels and Easton!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Brand New listing as of Oct 2022!! Excited for your stay! This completely renovated WATERFRONT 4 bedroom/4 bath home is ...
From $763 per night (USD)Expedia
From $1225 per night (USD)VRBO
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 12
Talbot County Rental License: ST-214-LYT If you do not see availability for your dates or are looking for a more modera ...
From $1225 per night (USD)VRBO
From $714 per night (USD)VRBO
New dates released! Enjoy reflections of sunsets and golden leaves on the water!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-762-OSM Just minutes from St Michaels this contemporary home is the perfect waterfront retreat. Offered for th ...
From $714 per night (USD)VRBO
From $892 per night (USD)VRBO
Beautiful historic waterfront home on 30+ acres
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: ST-483-SHA An historic estate situated on the northern headwaters of Island Creek. A home surrounded by 30 ac ...
From $892 per night (USD)VRBO
From $300 per night (USD)VRBO
House close to Great Marsh Park and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $300 per night (USD)VRBO
From $298 per night (USD)VRBO
Great prices on a available days left!!! Beautiful Leadenham Creek. STR #22-30
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Offering a HOMEY rental on the gorgeous Chesapeake Bay - Leadenham Creek, Bozman, MD. The Gnome Home is nestled on 3 1 ...
From $298 per night (USD)VRBO
From $492 per night (USD)Expedia
Waterfront - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM LANDING
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Talbot County MD License #STRN-22-41 Water front home nestled in quaint village of Bozman with dock/pier for fishing, ...
From $492 per night (USD)Expedia
Click For PricingVRBO
Historic 1918 House 1/2 Block from the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
Click For PricingVRBO
From $350 per night (USD)VRBO
Waterfront Vintage Eastern Shore Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Cedar Grove Beach is a lovely vintage Eastern Shore property perfect for a family vacation or a group of friends to get ...
From $350 per night (USD)VRBO
From $269 per night (USD)VRBO
Little Creek Hideaway - Privacy and Perfect Family Getaway.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Come relax at Little Creek Hideaway, the perfect family getaway during any season. Located just 10 minutes from Easton, ...
From $269 per night (USD)VRBO
From $481 per night (USD)Expedia
Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully decorated Harris Creek waterfront home is waiting for you! With plenty of room for multiple families to ...
From $481 per night (USD)Expedia
From $521 per night (USD)VRBO
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels
- 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 $521 per night (USD)VRBO
From $995 per night (USD)VRBO
Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
4+ acres on Shipshead Creek off of St. Michaels Road. Fully furnished (2 king and 4 twin beds), pool, hot tub, deep wate ...
From $995 per night (USD)VRBO
From $739 per night (USD)VRBO
Judith's Garden - Quaint Waterfront Home Near Oxford - Pool, Grill, Kayaks!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License# STRN-22-9 Judith's Garden is a delightful home located off the beaten path, yet close to the ...
From $739 per night (USD)VRBO
From $759 per night (USD)Expedia
Mill Creek - Cool Contemporary Waterfront - Pool, Grill, Dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Cool waterfront contemporary with retro vibe Located on the serene banks of Skipton & Mill Creeks, this home offers plen ...
From $759 per night (USD)Expedia
From $1171 per night (USD)VRBO
Gorgeous Waterfront
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful waterfront home - well furnished large open house, great amenities including pool, game room and gym, Sonos so ...
From $1171 per night (USD)VRBO
From $1700 per night (USD)Expedia
Belle Aire Landing - Choptank River Family Compound
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 22
When a list of vocabulary words such as 'unique', 'remarkable', and 'spectacular' still fail to describe how special a p ...
From $1700 per night (USD)Expedia
From $774 per night (USD)VRBO
Luxurious waterfront home - Cèilidh
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful luxury waterfront home in historic downtown Oxford. A rare find with 2 piers, Beautiful luxury waterfront home ...
From $774 per night (USD)VRBO
From $1116 per night (USD)Expedia
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!
- 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 $1116 per night (USD)Expedia
From $303 per night (USD)VRBO
Caulk's Cove of St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A deep water pier with picturesque views make this a truly special spot for a weekend getaway or mini-vacation. With ple ...
From $303 per night (USD)VRBO
From $919 per night (USD)Expedia
Oak Hill at Snug Harbor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License #ST-273-OAK Oak Hill Highlights: - 4 bedrooms/4 bathrooms - 3500 square foot house - Almost ...
From $919 per night (USD)Expedia
From $235 per night (USD)VRBO
The Anchorage B&B - The Bounty
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $235 per night (USD)VRBO
From $823 per night (USD)Expedia
Whitehall Acres - Lovely and serene-the perfect spot to nurture your soul!
- Bedrooms:
- 5
- Bathrooms:
- 4
- 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 $823 per night (USD)Expedia
From $325 per night (USD)VRBO
Waterfront, cozy cottage with private pool on 27 acres of privacy
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private 27 acre estate is nestled a mere 200 feet from the banks of the Choptank River. Whether you have ha ...
From $325 per night (USD)VRBO
From $500 per night (USD)VRBO
Last guest said property was AMAZING.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: ST-557-LEE Just minutes from St. Michaels is the perfect get away. Start your day with a walk over to the loca ...
From $500 per night (USD)VRBO
From $517 per night (USD)VRBO
NEW Waterfront Listing Minutes from St. Michaels, Spectacular Sunsets, Elevator!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
License No. ST-573-GRE Summer and holidays: 4 Night Minimum Since this is a brand new listing on the market, you ...
From $517 per night (USD)VRBO
From $1221 per night (USD)Expedia
Tranquil Water - Looking to getaway, relax and recharge?
- 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 $1221 per night (USD)Expedia
From $809 per night (USD)VRBO
The Water House | Over The River And Through The Woods!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 9
Eastern Shore Vacation Rentals presents The Water House. Beautifully appointed with artwork and antiques, The Water Hous ...
From $809 per night (USD)VRBO
From $426 per night (USD)Expedia
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Waterfront Cottage Within Minutes to Historic St. Michaels. Kayaks and Bikes Included! Comfortably furnished an ...
From $426 per night (USD)Expedia
From $412 per night (USD)VRBO
Clearview - Big Amenities: Pool Hot Tub Amazing Views!
- 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 $412 per night (USD)VRBO
From $291 per night (USD)Expedia
Pride and Joy of Oxford - Charming Pet-Friendly Home in Historic Oxford!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
In-town cottage with loads of charm and easy walking to parks and restaurants Tucked away in the quaint, historic town o ...
From $291 per night (USD)Expedia
From $631 per night (USD)VRBO
Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Easy, One-Level Living Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play ...
From $631 per night (USD)VRBO
From $225 per night (USD)Expedia
Relaxing Waterfront Cottage Near St Michaels, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by ...
From $225 per night (USD)Expedia
From $1100 per night (USD)VRBO
NEW 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 $1100 per night (USD)VRBO
From $481 per night (USD)Expedia
Sunrise Cove - Pet-Friendly Waterfront Home, Hot Tub, Pool & Grill!
- 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 $481 per night (USD)Expedia
From $379 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 $379 per night (USD)VRBO
From $207 per night (USD)Expedia
Memory Lane - Charming Cottage in the Heart of Oxford, Pet Friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Charming Cottage in the heart of Oxford, within walking distance to all our favorite Oxford things! We call this circa 1 ...
From $207 per night (USD)Expedia
From $381 per night (USD)VRBO
Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relaxing Waterfront Cottage with Screened Porch, Kayaks and Bikes We love this cottage for what it is not - it isn't bus ...
From $381 per night (USD)VRBO
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated Watermans Cottage circa 1920. Wide water views and bay breezes! This fantastic 1920's Waterman's cottage has t ...
Click For PricingExpedia
From $911 per night (USD)VRBO
Pines at Barrett Cove
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Up to date cottage with fabulous outdoor kitchen One of our most popular houses, Pines at Barrett Cove offers virtually ...
From $911 per night (USD)VRBO
From $342 per night (USD)Expedia
Chesapeake Pines - Hot Tub Under the Stars & Gorgeous Sunsets, Pet-Friendly!
- 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 $342 per night (USD)Expedia
From $371 per night (USD)VRBO
Seventh Haven - An oasis of peace and relaxation!
- 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 $371 per night (USD)VRBO
From $155 per night (USD)VRBO
Historic Marina District-2 BR/1 Ba-River View-Ironman Route-AC-Laundry-Walkable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Updated Victorian in historic district. Sleeps 4 in a large bedroom and a small bedroom (which can be set up for sleepin ...
From $155 per night (USD)VRBO
From $286 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 $286 per night (USD)VRBO
From $660 per night (USD)Expedia
Riverview Retreat - Charming Waterfront Cottage in St Michaels!
- 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 $660 per night (USD)Expedia
From $943 per night (USD)VRBO
Large Waterfront Home 2 miles from town
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Baydream Believer Formerly known for shipbuilding and oystering, St. Michaels, Maryland, calls itself “The Heart & Soul ...
From $943 per night (USD)VRBO
From $978 per night (USD)VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and absorb the beauty of living on the water at our 23 acre waterfront property on Harris Creek, in between histor ...
From $978 per night (USD)VRBO
From $242 per night (USD)VRBO
Historic Cambridge Home: Near Choptank River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Situated in the historic ‘West End’ of Cambridge, this 3-bedroom, 2-bath vacation rental has it all! ‘Cambridge Cottage’ ...
From $242 per night (USD)VRBO
From $719 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 $719 per night (USD)Expedia
From $999 per night (USD)VRBO
Modern Rustic Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Our serene colonial waterfront 5000 sq ft sanctuary holds the shore to its heart with water views from every floor and w ...
From $999 per night (USD)VRBO
From $550 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 $550 per night (USD)VRBO