Talbot Area Rentals
- From $900 per night (USD)
VRBO
Close to Everything!Surrounded By Water! Dock and Pool. A VIP Vacation Property.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
STN-23-3 NEW MASTER BATH RENOVATION! At the end of the long, private driveway, you will find a lovely home situated on 2 ...
From $900 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 $559 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 $559 per night (USD)VRBO
- From $555 per night (USD)
VRBO
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)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 $713 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 $713 per night (USD)Expedia
- From $685 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 $685 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy & Spacious, The Calway Inn
- Bedrooms:
- 1
- Bathrooms:
- 11
- Sleeps:
- 6
Summary: Take it easy at this unique and tranquil getaway. Situated right in the heart of this Talbot town, the Calway I ...
Click For PricingExpedia
- 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 $665 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 $665 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 $416 per night (USD)
Expedia
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 $416 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interio ...
From $489 per night (USD)VRBO
- From $803 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides ...
From $803 per night (USD)Expedia
- From $290 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 $290 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Grandview - Main House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
GRANDVIEW, which was once known as Grandview at Pleasure Point, is a private estate located on 5¼ acres of Maryland’s f ...
From $775 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Downtown Oxford | Charming | Outdoor Dining
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This charming 4-bedroom, 3.5-bathroom cottage in the historic town of Oxford was designed with your vacation in mind. Th ...
From $500 per night (USD)VRBO
- From $281 per night (USD)
Expedia
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 $281 per night (USD)Expedia
- From $463 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License #STN-22-4 This exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior an ...
From $463 per night (USD)VRBO
- From $373 per night (USD)
Expedia
A Luxury Home located in Easton with Water VIEWS! Close to Oxford\/St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LOW CLEANING FEE!! * If you need other accommodations for length of stay, please contact me directly. Newly remodel ...
From $373 per night (USD)Expedia
- From $1262 per night (USD)
VRBO
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 $1262 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 $504 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 $504 per night (USD)VRBO
- From $473 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License #ST-643-DER Originally a waterman's cottage, Neavitt Cottage has been tastefully updated (sup ...
From $473 per night (USD)Expedia
- From $255 per night (USD)
VRBO
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 ...
From $255 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License #ST-825-OAK Built in 1930, this 5-bedroom, 3.5-bathroom waterfront getaway sits on 2.2 acres ...
From $650 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License #ST-578-shi This 3-bedroom, 2-bathroom offers an open floor plan character-filled interior an ...
From $321 per night (USD)VRBO
- From $395 per night (USD)
Expedia
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 $395 per night (USD)Expedia
- From $426 per night (USD)
VRBO
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 $426 per night (USD)VRBO
- From $723 per night (USD)
Expedia
Beautiful Waterfront Home with POOL minutes from St. Michaels and Easton!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This completely renovated WATERFRONT 4 bedroom/4 bath home is tucked away on a beautiful, quiet cove on Solitude Creek, ...
From $723 per night (USD)Expedia
- From $1395 per night (USD)
VRBO
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)VRBO
- From $1786 per night (USD)
Expedia
Thorneton Point Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Nestled on the tip of an idyllic private 5 acre peninsula, minutes from historic St. Michaels, Thorneton Point ...
From $1786 per night (USD)Expedia
- From $1035 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Kayaks | Pool | Private Dock
- 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 $1035 per night (USD)VRBO
- From $700 per night (USD)
Expedia
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 $700 per night (USD)Expedia
- From $450 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 $450 per night (USD)VRBO
- From $2079 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Eastern Shore Vacation Rentals presents Fairview Estate. Tranquil and timeless, Fairview is among the great historic est ...
From $2079 per night (USD)Expedia
- From $2072 per night (USD)
VRBO
Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Your Unforgettable Waterfront Retreat! Escape to the unparalleled luxury of Eventide Farm, a waterfront retreat in St. ...
From $2072 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mi ...
From $1000 per night (USD)Expedia
- From $513 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License STN-23-31 Welcome to Gratitude Farm, a newly renovated 1890s farmhouse offering the ultimate ...
From $513 per night (USD)VRBO
- From $312 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Newly Renovated | Kayaks | Cha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore Vacation Rentals presents Banyan Cottage. This impressive and simply idyllic 2BR/2BA vacation cottage is t ...
From $312 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $467 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents American Pride. Don’t miss this truly exceptional 1950's ranch style 3BR, 2.5BA ...
From $467 per night (USD)Expedia
- Click For Pricing
VRBO
Sunset Vista | an ESVR property
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents Sunset Vista. Cross the historic Tilghman Island bridge and experience the adven ...
Click For PricingVRBO
- Click For Pricing
Expedia
Private Waterfront Cottage on Bolingbroke Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally Private, quiet water-front cottage with wood burning fireplace and exclusively private 60' Lap Pool(open mid-Apr ...
Click For PricingExpedia
- From $700 per night (USD)
VRBO
NEWLY Renovated Waterfront Farmhouse in Private Setting!!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STN-23-12 This charming 16+ acre waterfront farmhouse circa 1769 just underwent a massive renovation and interior redesi ...
From $700 per night (USD)VRBO
- From $396 per night (USD)
Expedia
NEW LISTING! 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 met ...
From $396 per night (USD)Expedia
- From $414 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 $414 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Simplicity Cottage renovated Waterman's cottage circa 1920's- Wide water views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-58 Renovated Watermans Cottage circa 1920. Wide water views and bay breezes! This fantastic 1920's Waterman's co ...
From $350 per night (USD)VRBO
- Click For Pricing
VRBO
Vacation Rental in Historic St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right ab ...
Click For PricingVRBO
- From $280 per night (USD)
Expedia
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This bright and airy 3BR, 2BA cape cod vacation home in Oxford is designed with your comfort in mind. The free-flowing f ...
From $280 per night (USD)Expedia
- From $830 per night (USD)
VRBO
Enjoy the beautoful reflections of sunsets and the golden leaves on the water!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-23-30 Just minutes from St Michaels this contemporary home is the perfect waterfront retreat. Offered for the f ...
From $830 per night (USD)VRBO
- From $235 per night (USD)
Expedia
B&B - The Lawson
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This delightful bed & breakfast is the perfect home base for your visit. The property includes a small beach, Adirondack ...
From $235 per night (USD)Expedia
- From $3094 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Pool House | Lu
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 12
Vacation like a rockstar at this 21+ acre luxury waterfront estate located on a protected cove off the Tred Avon River. ...
From $3094 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy 2BR Home near Idlewild Park\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
"Welcome to your cozy retreat in the heart of Easton, Maryland, a small, charming town nestled on Maryland's Eastern Sho ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
License # STN-23-39...(3 night minimum off season.) A long, driveway on two, private acres, leads to this updated and ch ...
From $450 per night (USD)VRBO
- From $149 per night (USD)
VRBO
Charming House in a Quiet Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful house has it all. The charm of a 1960s brick ranch with a fully updated interior. All new flooring, new ...
From $149 per night (USD)VRBO
- From $650 per night (USD)
VRBO
New St Michaels Waterfront
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: A private waterfront home with coastal chic design, sweeping water views, endless sunsets and luxe amenities al ...
From $650 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Book a week in July\/August & steamed crabs on us!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: As you head down the tree lined drive you will instantly know you are about to be somewhere special. A perfect ...
From $625 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Skipjack cottage an original watermen's home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: If you are looking for a peaceful & friendly area to getaway too, look no further. Once across the bridge you ...
From $295 per night (USD)VRBO
- From $571 per night (USD)
VRBO
Ferry Bridge House
- Bedrooms:
- 5
- 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 $571 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County Rental License STRN-23-19 Stunning 22 acre property in prime location on the Tred Avon situated between ...
From $900 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Fabulous SUMMER rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This newly built cottage is located in the quaint waterman's community of Tilghman Island. The perfect spot to ...
From $215 per night (USD)VRBO
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Modern Comfort in a Cozy Chalet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Nestled on a side street in St, Michaels , this two bedroom, two bathroom retreat is thoughtfully designed to p ...
From $350 per night (USD)VRBO
- Click For Pricing
VRBO
NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1\/2 bths - dock & pool STN-23-23
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
STN-23-23 - First time offered waterfront located on Boone Creek between Oxford and Easton. Home features 5 bedrooms - ...
Click For PricingVRBO
- 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 $564 per night (USD)
VRBO
Waterfront Minutes from Christmas in St. Michaels. Hot Tub, Elevator.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Another Luxury VIP Vacation Rental Property License # STRN-22-25 Stay at this comfortable property minutes from the fe ...
From $564 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 $1586 per night (USD)
VRBO
Breathtaking Waterfront Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private d ...
From $1586 per night (USD)VRBO
- From $795 per night (USD)
Expedia
Waterfront - NEW BOOK 2024 AND RECEIVE 100 Gift CERT FOR SEAFOOD FROM \nLANDING
- 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 $795 per night (USD)Expedia
- From $717 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 $717 per night (USD)VRBO
- From $790 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. Private large pool (salt water) and dock. Location is a c ...
From $790 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Breathtaking Views & Tranquility
- 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 $995 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Waterfront Bliss, Spectacular Views, NEW RATES
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Wake to the sun rising over Harris Creek, where breathtaking views meet unparalleled tranquility. Nestled along ...
From $450 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Unmatched Luxury Living
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Town licensed. This beautiful flat is located in the heart of the St Michael's historic district. Arrive to a ...
From $295 per night (USD)VRBO
- From $265 per night (USD)
VRBO
Historic Home in Heart of Oxford, MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in a historic home built by the railroad when it came to town in 1880 (look for Pennsylvania Railroad memorabilia t ...
From $265 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Time to make those summer plans!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: STN-22-12 This waterman's community is rich in the traditions of working on the water. The spirit of Tilghman ...
From $250 per night (USD)VRBO
- From $1020 per night (USD)
VRBO
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, close walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County Short-Term Rental License STN-23-2 Villa estates ...
From $1020 per night (USD)VRBO
- From $682 per night (USD)
VRBO
Secluded Waterfront Property on 3 acres with swimming pool and dock.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Open floor plan home with ample views of the Leadenham Creek. Salt water swimming pool overlooks 220 feet of shoreline ...
From $682 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Modern Studio in heart of town, walk everywhere!
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $250 per night (USD)
VRBO
Luxurious studio in heart of historic St Michaels!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Town licensed Let us know if you'd like a bottle of your favorite wine or charcuterie upon arrival. Its the pe ...
From $250 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Delightful Close to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay near Saint Michaels and enjoy a wonderful town and a great stay. There is lots to do and shop for in the quaint tow ...
From $625 per night (USD)VRBO
- From $144 per night (USD)
VRBO
Adorable two-bedroom retreat close to Easton, Denton, Centreville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax in this quiet, renovated bungalow just a short bike ride to Tuckahoe State Park, the Eastern Shore's largest state ...
From $144 per night (USD)VRBO
- From $271 per night (USD)
Expedia
Dorchester County Home Near Choptank River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Head to Cambridge, Maryland, for a relaxing retreat on the Eastern Shore! Located between the Choptank River and the his ...
From $271 per night (USD)Expedia
- From $1050 per night (USD)
VRBO
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
Choptank oasis offers the perfect Eastern Shore experience: 200' pier great for crabbing and fishing, river kayaking/ca ...
From $1050 per night (USD)VRBO
- From $533 per night (USD)
Expedia
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 $533 per night (USD)Expedia
- From $354 per night (USD)
VRBO
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 $354 per night (USD)VRBO
- From $550 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 $550 per night (USD)Expedia
- Click For Pricing
VRBO
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 $2135 per night (USD)
Expedia
Short drive to Downtown Cambridge | Private Dock | Sleeps 22 | Pool | Hot Tub |
- 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 $2135 per night (USD)Expedia
- From $434 per night (USD)
VRBO
Cozy Cambridge Retreat w\/ Casita Near Marina!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your next family retreat awaits at this 4-bedroom, 3-bath home featuring a spacious casita! With its central location, t ...
From $434 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $175 per night (USD)Expedia
- From $800 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 $800 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- 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 $518 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $518 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 $417 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This remolded waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is f ...
From $417 per night (USD)VRBO
- From $504 per night (USD)
VRBO
Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $504 per night (USD)VRBO
- From $706 per night (USD)
VRBO
Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a 4 Bedroom, 3.5 Bath LUXURY townhouse overlooking the 1st hole of the RiverMarsh Golf Course at the Hyatt Regency ...
From $706 per night (USD)VRBO