Talbot Area Rentals
- From $473 per night (USD)
VRBO
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)VRBO
- From $322 per night (USD)
Expedia
Walk to Everything House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The historic house which was restored from 2016-2020, is conveniently located on a quiet street near the Blue Crab coffe ...
From $322 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 $1500 per night (USD)
VRBO
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on ...
From $1500 per night (USD)VRBO
- From $195 per night (USD)
VRBO
5 bedroom Bed and Breakfast on the Choptank River
- Bedrooms:
- 1
- 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 $195 per night (USD)VRBO
- Click For Pricing
VRBO
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy your own private condo-style Junior Suite, and suite cottage at Sandaway Suites & Beach in Oxford, MD. Please note ...
Click For PricingVRBO
- Click For Pricing
VRBO
Upgraded King at Boutique Hotel, Private Beach, Walk to Restaurants & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and ...
Click For PricingVRBO
- Click For Pricing
VRBO
Town View King Apartment with Private Beach - Walk to shops and restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy our Chesapeake Bay Vacations rental in charming Oxford, Maryland! Sandaway Suites & Beach in Oxford, MD is an excl ...
Click For PricingVRBO
- 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 $409 per night (USD)
Expedia
Downtown Oxford | Boat Slip | Bikes | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bright and airy, 4-bedroom, 3-bathroom home features a first-floor bedroom with bath as well as an updated gourmet kitch ...
From $409 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 $704 per night (USD)
Expedia
Waterfront Property, kayaks, private dock, near town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginnin ...
From $704 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Stylish Home on the Choptank River (with Tidal Beach)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to the River House! Stay in our newly renovated salt-box style home on the Choptank River of Maryland's Eastern ...
From $205 per night (USD)VRBO
- From $321 per night (USD)
Expedia
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)Expedia
- From $944 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Kayaks | Pool | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Built in 1800, this 5-bedroom, 3-bathroom historic colonial shore house sits on 3.5+ acres and boasts endless nautical a ...
From $944 per night (USD)VRBO
- From $1339 per night (USD)
VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $1339 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
- From $889 per night (USD)
Expedia
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to e ...
From $889 per night (USD)Expedia
- From $567 per night (USD)
VRBO
Cambridge Beach Home on Choptank River w\/ Pier!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Your next waterfront retreat awaits at this 5-bedroom, 3-bath Cambridge vacation rental! This lovely property features 5 ...
From $567 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 $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 $399 per night (USD)
VRBO
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 $399 per night (USD)VRBO
- From $225 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 $225 per night (USD)VRBO
- 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 $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)
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 $144 per night (USD)Expedia
- 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 $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 $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 $907 per night (USD)
VRBO
NEW! Gorgeous Waterfront Estate with 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 $907 per night (USD)VRBO
- From $240 per night (USD)
VRBO
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 $240 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 $744 per night (USD)
Expedia
Minutes from Downtown Cambridge | Outdoor Dining | Private Dock | Kayaks | Bikes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
This gorgeous two-story 5,000 square foot, 4-bedroom, 3.5-bathroom waterfront estate was designed with your comfort in m ...
From $744 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
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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 PricingExpedia
- From $307 per night (USD)
VRBO
Stylish Victorian in Historic District
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Located in the heart of the peaceful Historic District of Cambridge, this Victorian stunner c. 1912 is the place to book ...
From $307 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 $271 per night (USD)
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 ...
From $271 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Modern Studio in heart of town.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Let us know if you'd like a bottle of your favorite wine and charcuterie upon arrival. Its the perfect start to ...
From $250 per night (USD)VRBO
- From $373 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 $373 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County License #ST-611-SMI Elegantly furnished and located in a prestigious estate area of Talbot County, Blue G ...
From $1200 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Eastern Shore Waterside Cottage Near St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A completely renovated (2023) cottage on private wooded lot in the quaint, water side, historic community of Neavitt MD. ...
From $297 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
- 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 $950 per night (USD)
VRBO
A Waterfront Escape Like No Other
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: The Farm at Bald Eagle Point is the great escape! Our guests can settle in and never have to leave this exclusi ...
From $950 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Charming 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 ...
From $360 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Sky View. The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is cre ...
From $550 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $275 per night (USD)
VRBO
Quaint Tilghman Island home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Vacation home minutes from St Michaels. Tucked away on a quiet neighborhood street is the Wandering Loon. A pe ...
From $275 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Warmth and Comfort Await
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Step into a thoughtfully curated space where coastal decor meets serene comfort. The open-concept living area i ...
From $295 per night (USD)VRBO
- From $350 per night (USD)
VRBO
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 $350 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Cozy Home in Historic West End Perfect for Ironman
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your getaway in historic Cambridge in our spacious & serene home. Located in the Historic West End, the home comf ...
From $295 per night (USD)VRBO
- From $467 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 $467 per night (USD)VRBO
- Click For Pricing
Expedia
Your “Happy Place”-Updated beautifully 3 story home on quiet island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local se ...
Click For PricingExpedia
- From $829 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Pool | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Family Tides. The impressive 4BR, 3.5BA waterfront along Irish Creek is designed ...
From $829 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- 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 $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 $325 per night (USD)
VRBO
A little slice of heaven on the Choptank River
- 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 $325 per night (USD)VRBO
- From $403 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 $403 per night (USD)Expedia
- From $239 per night (USD)
VRBO
Newly Renovated Guest House located in Oxford MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Mary ...
From $239 per night (USD)VRBO
- 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 $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 $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- 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 $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 $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 $499 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 $499 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 $628 per night (USD)
VRBO
Historic Elegance and Modern Luxury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This three bedroom, three bathroom cottage offers an exclusive escape, combining comfort and modern luxuries. I ...
From $628 per night (USD)VRBO
- From $434 per night (USD)
Expedia
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)Expedia
- 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
- From $513 per night (USD)
Expedia
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)Expedia
- From $299 per night (USD)
VRBO
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 $299 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Downtown Cambridge | Historic Charm | Modern Upgrades
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect location for an easy getaway in any season! Overlooking Cambridge's stunning marina and yacht club, this im ...
From $393 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Minutes from Downtown Cambridge | Private Dock | Kayaks | Bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This gorgeous 2-bedroom , 2-bathroom cottage waterfront was designed with your comfort in mind. Your search for the fin ...
From $400 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 $650 per night (USD)
VRBO
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 $650 per night (USD)VRBO
- From $350 per night (USD)
Expedia
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 $350 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Luxurious Living with Stunning Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Sunsets Edge , a true waterfront retreat. . This three bedroom, 2.5 bathroom home offers a unique bl ...
From $700 per night (USD)VRBO
- 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 $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 $1299 per night (USD)
VRBO
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 ...
From $1299 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 $345 per night (USD)
VRBO
Family friendly with a Pool and Game Room. Convenient Location with a view.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom ...
From $345 per night (USD)VRBO
- From $414 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 $414 per night (USD)Expedia
- 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 $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