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

Talbot Area Rentals

From $508 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Brand New Pool and Hot Tub Coming June 2024 This 2-bedroom, 2-bathroom waterfront getaway features a character-filled i ...
From $508 per night (USD)
VRBO
$Spacious Trappe Getaway w\/ Outdoor Pool & Gazebo!$
From $327 per night (USD)
Expedia
Spacious Trappe Getaway w\/ Outdoor Pool & Gazebo!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Retreat with family to this quiet and peaceful, 4-bedroom, 2.5-bathroom vacation rental in Trappe, Maryland. Relax on Ox ...
From $327 per night (USD)
Expedia
From $1059 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 $1059 per night (USD)
VRBO
$EASTON Beautiful APT. 2bed2bathKitchinDining\/living room-walk to all places$
From $711 per night (USD)
Expedia
EASTON Beautiful APT. 2bed2bathKitchinDining\/living room-walk to all places
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Downtown EASTON -Beautiful Mezzanine APARTMENT with cathedral celling's -2 bed 2bath- Kitchen Dining area large living r ...
From $711 per night (USD)
Expedia
$Easton \/ St. Michaels Retreat$
From $595 per night (USD)
VRBO
Easton \/ St. Michaels Retreat
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
POOL OPEN 3/25/24 Relax with the whole family at this peaceful place to stay. Welcome to Travelers Rest! A quiet and sec ...
From $595 per night (USD)
VRBO
From $533 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 $533 per night (USD)
VRBO
From $949 per night (USD)
VRBO
Waterfront,Dock,Pool.Private Point in Estate Area. Minutes from Everything!
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
NEW BATHROOM RENOVATIONS! At the end of the long, private driveway, you will find a lovely home situated on 2.20 acres o ...
From $949 per night (USD)
VRBO
From $363 per night (USD)
VRBO
Enjoy 3rd night free!
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Summary: Book 2 nights in July or August and get the 3rd night free! Located in the heart of historic St Michaels, this ...
From $363 per night (USD)
VRBO
From $641 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 $641 per night (USD)
VRBO
From $177 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 $177 per night (USD)
VRBO
From $859 per night (USD)
VRBO
Days have opened up in August, summers best rates!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: This private waterfront home is the perfect spot for a great vacation. Just minutes from all St Michaels has t ...
From $859 per night (USD)
VRBO
From $830 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 $830 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Duck Cove Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR License - ST-639-DUN Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)
VRBO
From $778 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 $778 per night (USD)
Expedia
From $1002 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 $1002 per night (USD)
VRBO
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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 Pricing
Expedia
From $310 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 $310 per night (USD)
VRBO
From $801 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 $801 per night (USD)
VRBO
From $1325 per night (USD)
VRBO
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
MID-WEEK SPECIAL- Mon - Thurs Nights $999. 1 Mile to St Michaels-THE ST MICHAELS HARBOR SHUTTLE CAN PICK YOU UP AT OUR D ...
From $1325 per night (USD)
VRBO
From $651 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 $651 per night (USD)
Expedia
From $868 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 $868 per night (USD)
VRBO
From $1131 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 $1131 per night (USD)
Expedia
From $280 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 $280 per night (USD)
VRBO
From $803 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 $803 per night (USD)
VRBO
From $710 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 $710 per night (USD)
VRBO
From $444 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 $444 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Waterfront Oasis of Peace and Relaxation! This 3-bedroom, 2-bathroom offers an open floor plan character-filled inter ...
From $557 per night (USD)
VRBO
From $643 per night (USD)
Expedia
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 $643 per night (USD)
Expedia
$A Luxury Home located in Easton with Water VIEWS! Close to Oxford\/St. Michaels$
From $398 per night (USD)
VRBO
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 $398 per night (USD)
VRBO
From $1633 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 $1633 per night (USD)
Expedia
From $1012 per night (USD)
VRBO
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 $1012 per night (USD)
VRBO
From $585 per night (USD)
Expedia
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 $585 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Shorely, this is a true outdoor paradise! Originally a waterman's cottage, Neavitt Cottage has been tastefully updated ...
From $660 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 ...
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Expedia
From $465 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 $465 per night (USD)
VRBO
From $432 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 $432 per night (USD)
Expedia
From $793 per night (USD)
VRBO
Beautiful Waterfront Home with POOL minutes from St. Michaels and Easton!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Completely renovated in spring 2022, WATERFRONT 4 bedroom/4 bath home is tucked away on a beautiful, quiet cove on Solit ...
From $793 per night (USD)
VRBO
From $1524 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 $1524 per night (USD)
Expedia
From $1157 per night (USD)
VRBO
Thorneton Point Estate
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: **HEATED POOL FROM 4/18** Nestled on the tip of an idyllic private 5 acre peninsula, minutes from historic St. ...
From $1157 per night (USD)
VRBO
From $987 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 $987 per night (USD)
Expedia
From $1283 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 $1283 per night (USD)
VRBO
From $431 per night (USD)
Expedia
August 1-30 rental available Oxford, MD. Very cute newly renovated house .
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Newly renovated charming house in the middle of town. 1 block from the Chesapeake bay, across the street from park/ play ...
From $431 per night (USD)
Expedia
From $1248 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Outdoor Kitchen | Private Dock | Hot
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Discover Your Peaceful Escape! Welcome to your dream vacation estate, an impressive 5-bedroom, 5-full bathroom, 1-half ...
From $1248 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Arcadia Shores on the Cove.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your home away from home in Easton with 4 bedrooms and 4 full baths. This sprawling rancher offers a tranquil and soothi ...
From $668 per night (USD)
Expedia
From $2083 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 $2083 per night (USD)
VRBO
From $1533 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 $1533 per night (USD)
Expedia
From $742 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 $742 per night (USD)
VRBO
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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 Pricing
Expedia
From $785 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 $785 per night (USD)
VRBO
From $2044 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 $2044 per night (USD)
Expedia
From $424 per night (USD)
VRBO
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 $424 per night (USD)
VRBO
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Expedia
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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Expedia
From $724 per night (USD)
VRBO
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 $724 per night (USD)
VRBO
From $1026 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Eastern Shore Vacation Rentals presents Leeds Landing. Situated on a quiet 2+acre waterfront lot, this home is perfect f ...
From $1026 per night (USD)
Expedia
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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 ...
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VRBO
From $2914 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Pool House | Lu
Bedrooms:
7
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 $2914 per night (USD)
Expedia
From $225 per night (USD)
VRBO
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 $225 per night (USD)
VRBO
$Cozy 2BR Home near Idlewild Park\n$
From $374 per night (USD)
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 ...
From $374 per night (USD)
Expedia
From $658 per night (USD)
VRBO
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 $658 per night (USD)
VRBO
From $855 per night (USD)
VRBO
Enjoy the beautiful 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. This home gives i ...
From $855 per night (USD)
VRBO
From $425 per night (USD)
VRBO
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 $425 per night (USD)
VRBO
$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$
From $371 per night (USD)
Expedia
\"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 $371 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
STRN-23-58 Simplicity Cottage is a circa 1920 Waterman's Cottage. Wide water views and bay breezes! This fantastic 1920' ...
From $426 per night (USD)
VRBO
Click For Pricing
VRBO
Great summer rates, Book today!
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 ...
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VRBO
From $369 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 $369 per night (USD)
VRBO
From $271 per night (USD)
VRBO
Stay 3 nights and 4th night is free!
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 $271 per night (USD)
VRBO
From $506 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 $506 per night (USD)
VRBO
From $712 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 $712 per night (USD)
VRBO
From $1083 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 $1083 per night (USD)
VRBO
From $825 per night (USD)
Expedia
Miles View Villa: Exquisite Waterfront Getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Welcome to Miles View Villa, your perfect escape from the hustle and bustle of everyday life. Nestled on the se ...
From $825 per night (USD)
Expedia
From $327 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 $327 per night (USD)
VRBO
$NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1\/2 bths - dock & pool STN-23-23$
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Expedia
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 - ...
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Expedia
From $440 per night (USD)
VRBO
Still time to join us in St Michaels this summer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Modern Comfort in a Cozy Chalet. Nestled on a side street in St, Michaels , this two bedroom, two bathroom retr ...
From $440 per night (USD)
VRBO
$LUXURY COASTAL FARMHOUSE WATERFRONT W\/ HEATED POOL$
From $1214 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 $1214 per night (USD)
VRBO
From $2443 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 $2443 per night (USD)
VRBO
From $672 per night (USD)
Expedia
Waterfront - pier and acreage to run & play. Pet friendly AVAILABLE AUG DATES
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Talbot County MD License #STN-24-6 Water front home nestled in quaint village of Bozman with dock/pier for fishing, cr ...
From $672 per night (USD)
Expedia
From $950 per night (USD)
VRBO
Trend Setting spacious Waterfront St. Michaels - PLAN YOUR FALL ESCAPE NOW!
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 $950 per night (USD)
VRBO
$Beautiful Waterfront Home w\/ Pool In St. Michaels$
From $693 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 $693 per night (USD)
VRBO
From $880 per night (USD)
VRBO
Great new rates July & August Book now!
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 $880 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Book 2 nights & Enjoy 3rd night free!
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
Summary: Book 2 nights in August/September and get the 3rd night free! Town licensed. This beautiful flat is located i ...
From $374 per night (USD)
VRBO
From $550 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 $550 per night (USD)
VRBO
From $620 per night (USD)
VRBO
Book 3 days in August and September get 4th free!
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 $620 per night (USD)
VRBO
From $631 per night (USD)
VRBO
Rent 4 Nites, 5th Nite FREE! Waterfront, Dock, Hot Tub, Elevator, Oxford Ferry.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Another Luxury VIP Vacation Rental Property License # STRN-22-25 Stay at this comfortable property minutes from the qu ...
From $631 per night (USD)
VRBO
From $209 per night (USD)
Expedia
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 $209 per night (USD)
Expedia
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 $1100 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 $1100 per night (USD)
VRBO
From $341 per night (USD)
VRBO
Best rates of the season, book today!
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 $341 per night (USD)
VRBO
From $724 per night (USD)
Expedia
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 $724 per night (USD)
Expedia
From $797 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 $797 per night (USD)
VRBO
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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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $207 per night (USD)
Expedia
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 $207 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $1349 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 $1349 per night (USD)
VRBO
From $651 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 $651 per night (USD)
VRBO
From $456 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 $456 per night (USD)
Expedia
From $901 per night (USD)
VRBO
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 $901 per night (USD)
VRBO
$Historic 1918 House 1\/2 Block from the Choptank River$
Click For Pricing
Expedia
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 Pricing
Expedia
From $2262 per night (USD)
VRBO
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 $2262 per night (USD)
VRBO
From $1198 per night (USD)
VRBO
The Wilder Way with a beautiful pool, hot tub, and a pickleball court!!
Bedrooms:
4
Bathrooms:
6
Sleeps:
23
If you’re looking for a place to go to relax with your family and friends look no farther! Surrounded by woodland and fi ...
From $1198 per night (USD)
VRBO

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Results: 236 Rentals