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 $683 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Enjoy “the good old days” in style! This exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior an ...
From $683 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Easter Weekend open WATERFRONT St Michaels area historic home, dog friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Full renovations completed in 2016 on this historic home. Sleeps four (1 King, 1 Queen, 1 Twin). Kick back, relax and e ...
From $457 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Perfect Waterview Cottage - St. Michaels Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shipwright Cottage is a fully-renovated idyllic getaway located in the Bay Hundred area of the Chesapeake Bay just 8 mil ...
From $248 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
From $739 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 $739 per night (USD)
VRBO
From $245 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 $245 per night (USD)
Expedia
From $892 per night (USD)
VRBO
Grandview - Main House
Bedrooms:
3
Bathrooms:
5
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 $892 per night (USD)
VRBO
From $852 per night (USD)
Expedia
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 $852 per night (USD)
Expedia
From $724 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 $724 per night (USD)
VRBO
From $443 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 $443 per night (USD)
Expedia
From $1895 per night (USD)
VRBO
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Bedrooms:
6
Bathrooms:
7
Sleeps:
20
Treat yourself to this unique waterfront retreat where you’ll enjoy stunning ocean liner views of the Choptank River fro ...
From $1895 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Cheerful three-bedroom Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Introducing River Light Cottage, the perfect escape in historic Cambridge, Maryland! A short walk from downtown shops an ...
From $256 per night (USD)
Expedia
From $907 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 $907 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Harbor View Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including th ...
From $294 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Cozy & Spacious, The Calway Inn
Bedrooms:
1
Bathrooms:
12
Sleeps:
6
Summary: Take it easy at this unique and tranquil getaway. Situated right in the heart of this Talbot town, the Calway I ...
From $194 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Stylish Victorian in Historic District
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Beware: not your typical VRBO A hunt has been set for you and your companions to follow the dramatized story of Eva Rob ...
From $407 per night (USD)
Expedia
From $854 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 $854 per night (USD)
VRBO
From $1378 per night (USD)
Expedia
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS JULY 19-23 and JULY 27-8/1 Fantastically Loc ...
From $1378 per night (USD)
Expedia
From $930 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 $930 per night (USD)
VRBO
From $1195 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 $1195 per night (USD)
Expedia
$A Luxury Home located in Easton with Water VIEWS! Close to Oxford\/St. Michaels$
From $419 per night (USD)
VRBO
A Luxury Home located in Easton with Water VIEWS! Close to Oxford\/St. Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This luxury home is nestled on a spacious lot, offering peaceful water views overlooking a beautiful pond. The 3-bedroom ...
From $419 per night (USD)
VRBO
From $1668 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Elegantly Appointed Estate with Fantastic Outdoor Areas Elegantly furnished and located in a prestigious estate area of ...
From $1668 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Eastern Shore Waterside Cottage Near St. Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to an idyllic retreat, nestled in the peaceful town of Neavitt, just a short drive from the charming village of ...
From $396 per night (USD)
VRBO
From $979 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 $979 per night (USD)
Expedia
From $1051 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Toto, There’s No Place Like This Vacation Home! The impressive 5BR, 3.5BA vacation estate with a free-flowing floor pla ...
From $1051 per night (USD)
VRBO
From $1431 per night (USD)
Expedia
Time Stands Still, While Memories Are Made.
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 $1431 per night (USD)
Expedia
From $1104 per night (USD)
VRBO
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Vacation With No Limits! The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is created by a sprawling inte ...
From $1104 per night (USD)
VRBO
From $352 per night (USD)
Expedia
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 $352 per night (USD)
Expedia
From $403 per night (USD)
VRBO
4-Bedroom Retreat: Modern, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Heart of the Island & Pet Friendly Retreat on Tilghman Island! Step into a thoughtfully curated space where coa ...
From $403 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Eastern Shore Vacation Rentals presents Oyster Cottage. Just a 10-minute drive from historic St. Michaels and Tilghman I ...
From $624 per night (USD)
Expedia
From $723 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
O Say, Can You See Your Next Vacation? Don’t miss this truly exceptional 1950's ranch style 3BR, 2.5BA waterfront on th ...
From $723 per night (USD)
VRBO
From $1255 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Pool | Kayaks
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Sha La La La … Fun For Everyone! The impressive 5BR, 3BA, 2 half BA waterfront along Irish Creek is designed with relax ...
From $1255 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Casual Bungalow close to Choptank River, sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A newly renovated pristine bungalow close to downtown Cambridge, MD. We are conveniently located near St. Michael, East ...
From $254 per night (USD)
VRBO
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Expedia
Harris Cottage. Charming waterfront with pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Pack up your pups and kids ! Bring the whole family to this great place with lots of room for fun. Play in the pool or k ...
Click For Pricing
Expedia
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 $2707 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
One Of A Kind! Tranquil and timeless, Fairview is among the great historic estates of Talbot County. Offering a total o ...
From $2707 per night (USD)
Expedia
From $345 per night (USD)
VRBO
A little slice of heaven on the Choptank River Sept 19 to 23 is now open
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A perfect getaway on our waterfront property .You will have your own private beach. You can enjoy crabbing ,fishing , ka ...
From $345 per night (USD)
VRBO
From $511 per night (USD)
Expedia
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 $511 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Newly Renovated Guest House located in Oxford MD
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Mary ...
From $274 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Romantic Waterfront Cottage with Amazing Sunsets
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located on the Chesapeake Bay side of Tilghman Island, our beautiful property is host to several cottages (one, two and ...
From $300 per night (USD)
Expedia
From $1033 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 $1033 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Studio in Downtown – Walk to Everything!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Spring and Summer weekends are filling fast with guest coming to explore our fabulous little town. Welcome ...
From $342 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 ...
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VRBO
From $343 per night (USD)
Expedia
New listing! Riverside Retreat on the Choptank River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $343 per night (USD)
Expedia
From $1060 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A Perfect Single-Story Waterfront Retreat! Situated on a quiet 2+acre waterfront lot, this home is perfect for active f ...
From $1060 per night (USD)
VRBO
From $945 per night (USD)
Expedia
An Afternoon Nap in the Hammock is a Must.
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 $945 per night (USD)
Expedia
From $2969 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 $2969 per night (USD)
VRBO
From $1639 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 $1639 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Magnificent Historic Home by Water is Ready!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Our house, built in 1736, is ideally located in the heart of historic Cambridge. Facing the Choptank River, it is 1/2 bl ...
From $610 per night (USD)
VRBO
From $177 per night (USD)
Expedia
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)
Expedia
From $805 per night (USD)
VRBO
3BR Home: Serene Escape, Pet-Friendly, Fireplace
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Step into a realm of sophistication, where high-end furnishings meet bespoke décor, creating a seamless fusion of modern ...
From $805 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Charming Stay, Just Minutes from Downtown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: A stylish home that has all one needs for a fabulous getaway. Our quaint town has a bustling main street filled ...
From $476 per night (USD)
Expedia
From $1044 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 $1044 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Luxury on the river, steps to downtown &boat ramp!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $526 per night (USD)
Expedia
$NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1\/2 bths - dock & pool STN-23-23$
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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 - ...
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VRBO
$EASTON Beautiful APT. 3bed3bathKitchinDining\/living room-walk to all places$
From $449 per night (USD)
Expedia
EASTON Beautiful APT. 3bed3bathKitchinDining\/living room-walk to all places
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Downtown EASTON -Beautiful Mezzanine APARTMENT with cathedral celling's -3 bed 3bath- Kitchen Dining area large living r ...
From $449 per night (USD)
Expedia
From $393 per night (USD)
VRBO
High Water Guest House<br>
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of h ...
From $393 per night (USD)
VRBO
From $837 per night (USD)
Expedia
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 $837 per night (USD)
Expedia
From $411 per night (USD)
VRBO
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 $411 per night (USD)
VRBO
$Waterfront St Michaels Vacation Rental w\/ Fire Pit$
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Expedia
Waterfront St Michaels Vacation Rental w\/ Fire Pit
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Wake up on the water with a stay at this stylish 3-bedroom, 3.5-bath, St Michaels vacation rental! Relax, recharge, and ...
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Expedia
From $350 per night (USD)
VRBO
Cozy Summer Cottage With Water view - Book today!
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 $350 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Family friendly with a Pool and Game Room. Convenient Location with a view.
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom ...
From $433 per night (USD)
Expedia
$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$
From $334 per night (USD)
VRBO
\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Tilghman Island “Point of View” is a waterfront property located on Tilghman Island, with a 270-degree water view ov ...
From $334 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Charming Summer Cottage – Relax and Unwind Here!
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 $355 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Artists, writers & creative minds IMAGINE YOUR GETAWAY 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 $422 per night (USD)
VRBO
From $748 per night (USD)
Expedia
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This m ...
From $748 per night (USD)
Expedia
From $582 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 $582 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
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 $1067 per night (USD)
Expedia
From $843 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 $843 per night (USD)
VRBO
From $670 per night (USD)
Expedia
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 $670 per night (USD)
Expedia
From $465 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 $465 per night (USD)
VRBO
From $475 per night (USD)
VRBO
3BR Retreat: Pet-friendly - 10 Mins to Town
Bedrooms:
3
Bathrooms:
1
Sleeps:
6
Be among the first to experience the charm and comfort of this thoughtfully designed home. This modern retreat boasts 3 ...
From $475 per night (USD)
VRBO
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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 $1021 per night (USD)
Expedia
Serene Waterfront Minutes from St Michaels.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Welcome to Miles View Villa, Your Waterfront Retreat. Embrace the tranquility of Miles View Villa, a sanctuary ...
From $1021 per night (USD)
Expedia
From $1386 per night (USD)
VRBO
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 $1386 per night (USD)
VRBO
From $670 per night (USD)
Expedia
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 $670 per night (USD)
Expedia
$Spacious Trappe Getaway w\/ Outdoor Pool & Gazebo!$
From $329 per night (USD)
VRBO
Spacious Trappe Getaway w\/ Outdoor Pool & Gazebo!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Retreat with family to this quiet and peaceful, 4-bedroom, 2.5-bathroom vacation rental in Trappe, Maryland. Relax on Ox ...
From $329 per night (USD)
VRBO
Click For Pricing
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. ...
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Expedia
From $2142 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 $2142 per night (USD)
VRBO
$Charming 4 bedroom in Historic Cambridge\n\n$
From $452 per night (USD)
Expedia
Charming 4 bedroom in Historic Cambridge\n\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $452 per night (USD)
Expedia
From $284 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 $284 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Upscale Condo in Historic Downtown Cambridge, Maryland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this fully renovated historic condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous d ...
From $334 per night (USD)
Expedia
$Cozy 2BR Home near Idlewild Park\n$
From $391 per night (USD)
VRBO
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 $391 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Duck Cove Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR License - STRN-24-52 Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $343 per night (USD)
Expedia
Waterviews, Comfort & Convenience!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Looking for some rest or relief…or perhaps just a little fun? This home is just steps away from the Cambridge Yacht Basi ...
From $343 per night (USD)
Expedia
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VRBO
Cozy 3 bedroom historic cottgage in Oxford, MD avialable Aug 2024
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom cottage/ 2 1/2 baths. Kitchen, living/ dining area. outdoor shower after coming from the beach 1 block away.Ou ...
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VRBO
From $680 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 $680 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Pet-Friendly Cottage – Ideal for Summer Getaways!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Fishin Frank's Cottage on Tilghman Island Tucked away in the charming Watermans community of Tilghm ...
From $368 per night (USD)
VRBO
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $426 per night (USD)
Expedia
The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to The Drinking Gourd...a freshly renovated 2-bedroom penthouse in the heart of the historic downtown district o ...
From $426 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Minutes from Downtown Cambridge and Downtown Easton | 104+ Acre Farm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Farmhouse Surrounded by Nature This charming 4BR, 4BA vacation home with 104+/- acres on the Choptank River is the perf ...
From $709 per night (USD)
VRBO
From $744 per night (USD)
VRBO
Midweek Deals Await – Reserve Your Stay Today!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Acorn Cottage sits on a private cove at the end of Oak Creek offering an open-concept living space that is bright, airy, ...
From $744 per night (USD)
VRBO
From $422 per night (USD)
VRBO
Pet-Friendly Waterfront House
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Summer Special: Book 4 Nights in June or July & Enjoy 10% off your stay! Welcome to this charming 2-bedroom wa ...
From $422 per night (USD)
VRBO
From $964 per night (USD)
Expedia
Family & Friends Paradise – Pool, BBQ, & More!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Summary: Gather your favorite people and make yourself at home in this bright, cheerful 3-bedroom retreat—just minutes f ...
From $964 per night (USD)
Expedia
$Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n$
From $251 per night (USD)
VRBO
Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Unwind in Wittman at this welcoming house. With 3 cozy bedrooms including a queen bed, full bed, and bunk bed, guests wi ...
From $251 per night (USD)
VRBO
From $1095 per night (USD)
Expedia
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This 4-bedroom house in Cambridge is perfect for your Eastern Shore experience. With 2 queen beds and 4 twin beds, guest ...
From $1095 per night (USD)
Expedia
From $1379 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 $1379 per night (USD)
VRBO
From $1007 per night (USD)
Expedia
Gorgeous retreat across from yacht club, the Choptank, and IronMan finish line!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The perfect location for an easy getaway in any season. The home is across the street from the IRONMAN Maryland finish l ...
From $1007 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
Welcome to Swan Hollow, a charming 3-bedroom, 2-full bathroom, 2-half bathroom tranquil retreat nestled down a picturesq ...
From $1026 per night (USD)
VRBO
$\Belle Aire Landing\ a Large Beautiful Waterfront Estate! Under New Management!$
From $2484 per night (USD)
Expedia
\"Belle Aire Landing\" a Large Beautiful Waterfront Estate! Under New Management!
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
*Under New Management for 2025!* When thinking about an amazing vacation, the words that come to mind should be like 'A ...
From $2484 per night (USD)
Expedia

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Results: 237 Rentals