Talbot Area Rentals
From $676 per night (USD)VRBO
ENDLESS SUNSETS ON THE EASTERN BAY
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-22 Book with us and receive 2 dozen crabs! Come enjoy the quaintness of Claiborne, MD, just 5 minutes from hist ...
From $676 per night (USD)VRBO
From $1180 per night (USD)VRBO
Historic Oxford Waterfront Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Bonfield Manor is located at the entrance of Oxford, a half-mile walk or bike ride to restaurants, shops and the Rivervi ...
From $1180 per night (USD)VRBO
From $516 per night (USD)VRBO
St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
As Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. H ...
From $516 per night (USD)VRBO
From $857 per night (USD)VRBO
20% Off 5 Night Min. Waterfront, Hot Tub, Pool,Minutes to St.Michaels.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
License No. STRN-24-4 Note: A Contract is Required to Be Signed This lovely home offers a large main house with a downs ...
From $857 per night (USD)VRBO
From $322 per night (USD)VRBO
Charming cottage along water with private pier, near St. Michaels Winery
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
In the delightful town of Bozman lies a snug, welcoming 1-bedroom cottage perfect for your upcoming holiday. As you step ...
From $322 per night (USD)VRBO
From $549 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 $549 per night (USD)VRBO
From $2729 per night (USD)VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Only a 15 Minute Drive to Downtown St. Michaels and Easton! Jewel of the Tred Avon | an ESVR property This 7,700 sq ft ...
From $2729 per night (USD)VRBO
From $352 per night (USD)VRBO
The B&B of Anchorage - Skipjack
- 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 $352 per night (USD)VRBO
From $1005 per night (USD)VRBO
Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shor ...
From $1005 per night (USD)VRBO
From $1638 per night (USD)Expedia
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS PET FRIENDLY
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD License #STRN-24-89 - The Cove At St. Michaels is a magnificent 15.5 acre estate property with ingrou ...
From $1638 per night (USD)Expedia
From $398 per night (USD)VRBO
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore esca ...
From $398 per night (USD)VRBO
From $741 per night (USD)VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $741 per night (USD)VRBO
From $382 per night (USD)VRBO
Stay in the HEART of Saint Michaels!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, resta ...
From $382 per night (USD)VRBO
From $374 per night (USD)Expedia
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $374 per night (USD)Expedia
From $821 per night (USD)VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $821 per night (USD)VRBO
From $601 per night (USD)VRBO
Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, three bedroom cottage is available for ...
From $601 per night (USD)VRBO
From $413 per night (USD)VRBO
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The house is a 2 bedroom 2 ...
From $413 per night (USD)VRBO
From $1203 per night (USD)Expedia
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD Short Term Rental License #STRN-23-12 Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5- ...
From $1203 per night (USD)Expedia
From $843 per night (USD)VRBO
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
All persons thinking about making a newbooking, should consider adding travel cancellation insurance, prior to booking. ...
From $843 per night (USD)VRBO
From $998 per night (USD)Expedia
Thorneton Point Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: **HEATABLE SPA** Nestled on the tip of an idyllic private 5-acre peninsula, minutes from historic St. Michaels ...
From $998 per night (USD)Expedia
From $967 per night (USD)VRBO
Breathtaking Waterfront Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: This isn't a typical waterfront rental. Durham-Hythe Estate is a private 7.5-acre peninsula compound with ove ...
From $967 per night (USD)VRBO
From $678 per night (USD)VRBO
House on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $678 per night (USD)VRBO
From $1583 per night (USD)VRBO
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $1583 per night (USD)VRBO
From $993 per night (USD)Expedia
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Step into history without sacrificing modern comforts. Combsberry is a 1730 waterfront estate nestled on 30 pr ...
From $993 per night (USD)Expedia
From $488 per night (USD)VRBO
We still have availability for August to October 2026 STR #22-30
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Offering a HOMEY rental on the gorgeous Chesapeake Bay - Leadenham Creek, Bozman, MD. The Gnome Home is nestled on 3 1 ...
From $488 per night (USD)VRBO
From $971 per night (USD)Expedia
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of hist ...
From $971 per night (USD)Expedia
From $374 per night (USD)VRBO
Relax or Play 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 $374 per night (USD)VRBO
From $1031 per night (USD)VRBO
Luxurious waterfront home - Cèilidh
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful luxury waterfront home in historic downtown Oxford. A rare find with 2 piers, Beautiful luxury waterfront home ...
From $1031 per night (USD)VRBO
From $1539 per night (USD)VRBO
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fanta ...
From $1539 per night (USD)VRBO
From $301 per night (USD)VRBO
The Anchorage B&B - The Bounty
- 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 $301 per night (USD)VRBO
From $1363 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was d ...
From $1363 per night (USD)VRBO
From $813 per night (USD)Expedia
Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience the ultimate Chesapeake Bay getaway on Tilghman Island! This stunning waterfront retreat will featu ...
From $813 per night (USD)Expedia
From $568 per night (USD)VRBO
🌊 Book Now for 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Another Luxury VIP Vacation Rental Property License # STRN-22-25 Can't do stairs?? No Problem! This home has an ELEVA ...
From $568 per night (USD)VRBO
From $924 per night (USD)Expedia
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Waterfront Cottage Within Minutes to Historic St. Michaels. Kayaks and Bikes Included! Comfortably furnished an ...
From $924 per night (USD)Expedia
From $947 per night (USD)VRBO
Tilghman | Pool | Private Dock | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Big Amenities: Pool Hot Tub Amazing Views! Clearview is the answer to your getaway needs. With a swimming pool, hot tub ...
From $947 per night (USD)VRBO
From $777 per night (USD)Expedia
Downtown Oxford | Charming | Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
In-town cottage with loads of charm and easy walking to parks and restaurants Tucked away in the quaint, historic town o ...
From $777 per night (USD)Expedia
From $816 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Easy, One-Level Living Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play ...
From $816 per night (USD)VRBO
From $277 per night (USD)Expedia
Relaxing Waterfront Cottage Near St Michaels, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by ...
From $277 per night (USD)Expedia
From $1593 per night (USD)VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, DOCK, GOURMET KITCHEN
- 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 $1593 per night (USD)VRBO
From $1023 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great location with plenty of room for friends and family. Wonderful outdoor spaces to enjoy! This little gem on the ban ...
From $1023 per night (USD)Expedia
From $533 per night (USD)VRBO
BOOK NOW FOR SPRING & SUMMER DATES.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STN-22-40 ONE OF OUR MOST SOUGHT AFTER PROPERTIES! MINUTES FROM ST. MICHAELS...... Peaceful retreat with breathtaking su ...
From $533 per night (USD)VRBO
Click For PricingExpedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An oasis of peace and relaxation! This 3-bedroom, 2.5-bathroom shingle style cottage offers a character-filled interior ...
Click For PricingExpedia
From $329 per night (USD)VRBO
Dollhouse in Central Historic St Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The ho ...
From $329 per night (USD)VRBO
From $1024 per night (USD)Expedia
Downtown St. Michaels | Bikes | Kayaks | Private Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Waterfront Cottage in St Michaels Begin your day at Riverview Retreat with a beautiful sunrise and be amazed wi ...
From $1024 per night (USD)Expedia
From $1164 per night (USD)VRBO
Baydream Believer
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
BAYDREAM BELIEVER This home is a waterfront wonderland with plenty to do, from tubing and boating to fishing and cra ...
From $1164 per night (USD)VRBO
From $1277 per night (USD)VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and absorb the beauty of living on the water at our 23 acre waterfront property on Harris Creek, in between histor ...
From $1277 per night (USD)VRBO
From $621 per night (USD)VRBO
St. Michaels Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful waterfront home sits just over the bridge entering St. Michaels in a prime location. Breathtaking waterf ...
From $621 per night (USD)VRBO
From $374 per night (USD)Expedia
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $374 per night (USD)Expedia
From $1387 per night (USD)VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Hot Tub, Pool and Cabana House … Oh My! Built in 1930, this 5-bedroom, 3.5-bathroom waterfront getaway sits on 2.2 acre ...
From $1387 per night (USD)VRBO
From $329 per night (USD)Expedia
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $329 per night (USD)Expedia
From $527 per night (USD)VRBO
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Tilghman Island, a historic Chesapeake Bay community known for its working waterfront, friendly loca ...
From $527 per night (USD)VRBO
From $1092 per night (USD)Expedia
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Ingleton! EARLY CHECKIN AND LATECHECKOUT OCTOBER. Relax by the pool. Fish or crab or picnic at the end of t ...
From $1092 per night (USD)Expedia
From $493 per night (USD)VRBO
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Waterfront, 2 bedroom, 2 bath Private Cottage on Solitude Creek. 3.4 miles to St. Michaels and Oxford; 1 1/2 hours to O ...
From $493 per night (USD)VRBO
From $856 per night (USD)Expedia
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 $856 per night (USD)Expedia
From $361 per night (USD)VRBO
Walk to Everything House
- Bedrooms:
- 1
- 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 $361 per night (USD)VRBO
From $630 per night (USD)Expedia
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your home away from home in the heart of historic St. Michaels. Located on a peaceful residential street, this ...
From $630 per night (USD)Expedia
From $349 per night (USD)VRBO
Modern room with walk in shower and kitchenette
- 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 $349 per night (USD)VRBO
From $280 per night (USD)VRBO
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Eastern Shore MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy your own private condo-style Junior Suite at Sandaway Suites & Beach in Oxford, MD. Please note this is a Town Vie ...
From $280 per night (USD)VRBO
From $333 per night (USD)VRBO
Sandaway Suites & Beach Boutique Hotel, Private Beach, Walk to Dining & 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 ...
From $333 per night (USD)VRBO
From $333 per night (USD)VRBO
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Oxford, Maryland
- 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 ...
From $333 per night (USD)VRBO
From $900 per night (USD)VRBO
Waterfront Property, kayaks, private dock, near town
- Bedrooms:
- 2
- 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 $900 per night (USD)VRBO
From $1246 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 $1246 per night (USD)VRBO
From $720 per night (USD)VRBO
Adorable, well-appointed cottage on 2 ac. overlooking beautiful Long Haul Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Note: Cleaning and linen fee $200.00 License # STRN-24-69...Note: Cleaning and linen fee only $200! Sleeps 6. Reviews s ...
From $720 per night (USD)VRBO
From $763 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 $763 per night (USD)Expedia
From $1048 per night (USD)VRBO
Waterfront home with private dock near St. Michaels & Easton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy breathtaking water views from your private dock while staying just minutes from the charm of downtown St ...
From $1048 per night (USD)VRBO
From $1688 per night (USD)Expedia
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 $1688 per night (USD)Expedia
From $727 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dragonfly Cove offers an idyllic retreat just a seven minute drive from the heart of St. Michaels, Maryland. This charmi ...
From $727 per night (USD)VRBO
From $427 per night (USD)Expedia
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
- Bedrooms:
- 2
- 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 $427 per night (USD)Expedia
From $1302 per night (USD)VRBO
Heated pool, sandy beach, pier, and playground set punch point apart!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
TREMEZZO STAY - PUNCH POINT Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury re ...
From $1302 per night (USD)VRBO
From $355 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 $355 per night (USD)VRBO
From $441 per night (USD)VRBO
Cozy 2BR Home near Idlewild Park
- 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 $441 per night (USD)VRBO
From $174 per night (USD)Expedia
3-bedroom historic vacation home newly renovated in the middle of Oxford MD.
- Bedrooms:
- 2
- 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 $174 per night (USD)Expedia
From $767 per night (USD)VRBO
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 $767 per night (USD)VRBO
From $389 per night (USD)Expedia
Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Maryland's beautiful Eastern Shore and experience the peaceful charm of Tilghman Island. Whether you ...
From $389 per night (USD)Expedia
From $878 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 $878 per night (USD)VRBO
From $540 per night (USD)Expedia
Waterfront House in Saint Michaels: Pets Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to this charming 2-bedroom waterfront home in Saint Michaels! Enjoy a perfect blend of relaxation and c ...
From $540 per night (USD)Expedia
From $1022 per night (USD)VRBO
Saint Michaels Summer Retreat with Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A thoughtfully designed summer retreat just minutes from St. Michaels. Enjoy sun-filled days by the private po ...
From $1022 per night (USD)VRBO
From $232 per night (USD)Expedia
Cozy getaway! Centrally located between St. Michaels and Tilghman Island
- 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 $232 per night (USD)Expedia
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Minutes from Downtown St. Michaels | Pool | Outdoor Kitchen | Private Dock | Hot
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Discover Your Peaceful Escape! Welcome to your dream vacation estate, an impressive 5-bedroom, 5-full bathroom, 1-half ...
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From $1283 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
- Bedrooms:
- 3
- 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 $1283 per night (USD)Expedia
From $691 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Love at First Sight Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque ...
From $691 per night (USD)VRBO
From $1309 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location , Location, Location Escape to this stunning cedar Lindal home on the Eastern Shore, just a short drive from h ...
From $1309 per night (USD)Expedia
From $325 per night (USD)VRBO
Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Pot Pie Cottage — your charming, well-priced escape just minutes from the historic town of St. Mich ...
From $325 per night (USD)VRBO
From $449 per night (USD)Expedia
Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stay close to everything St. Michaels has to offer. This charming 3-bedroom cottage is within easy walking or ...
From $449 per night (USD)Expedia
From $423 per night (USD)VRBO
Bucolic setting awaits. Close to St. Mikes & steps to dock of bay. STRN26-6
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Claiborne and feel the calm from this 3-bedroom house. With 2 queen beds, 1 full bed, and 1 twin ...
From $423 per night (USD)VRBO
From $458 per night (USD)VRBO
3Br/1Ba Pondview Langsdale House - A Historic Stay with Heart
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Pondview Langsdale House – A Historic Stay with Heart Step into a piece of Easton’s rich history at The Pondview Lan ...
From $458 per night (USD)VRBO
From $694 per night (USD)VRBO
Downtown Oxford | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahoy there, mateys! Prepare to be captivated by this newly renovated 3-bedroom, 2-bathroom vacation rental in Oxford, ...
From $694 per night (USD)VRBO
From $629 per night (USD)Expedia
Brand-New Pool! Waterfront Bozman Village Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5 ...
From $629 per night (USD)Expedia
From $801 per night (USD)VRBO
Beautiful 3-bedroom Miles River waterfront in tranquil Easton - Relax and unwind
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Easton at this beautiful newly refreshed waterfront home nestled in private cove on 47 acres of river and farm ...
From $801 per night (USD)VRBO
From $577 per night (USD)Expedia
Minutes from Downtown St. Michaels | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
TGIF … Escape to happiness, laughter, and unforgettable moments at The Weekender! This bright and airy 2-bedroom, 2.5- ...
From $577 per night (USD)Expedia
From $1015 per night (USD)VRBO
Waterfront Paradise | Pool, Views & Serenity
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on ...
From $1015 per night (USD)VRBO
From $720 per night (USD)Expedia
The Farm at Cedar Cove | an ESVR property
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront Eastern Shore Retreat | 18 Acres | Private & Secluded Sleeps 6 · 3 Bedrooms · 3 Bathrooms · Completely Renov ...
From $720 per night (USD)Expedia
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Bayview 2.0 | an ESVR property
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Escape to Bayview 2.0, a stunning waterfront retreat within a few miles of charming St. Michaels. Designed for unforgett ...
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From $280 per night (USD)Expedia
“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Easton like a local in this cozy 2-bedroom home located in a pleasant, quiet neighborhood. This delightful pr ...
From $280 per night (USD)Expedia
From $1006 per night (USD)VRBO
St. Michaels Waterfront Home with Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Tucked along the peaceful waters of Maryland’s Eastern Shore, this newly constructed waterfront retreat was de ...
From $1006 per night (USD)VRBO
From $1009 per night (USD)Expedia
Tilghman | Pool | Private Dock | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Waterfront Bliss, your ultimate private waterfront retreat nestled in picturesque Tilghman Island, Maryland. ...
From $1009 per night (USD)Expedia
From $563 per night (USD)VRBO
Downtown St. Michaels | Porch + Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay in the heart of downtown St. Michaels in this charming, professionally managed studio apartment, perfectl ...
From $563 per night (USD)VRBO
From $472 per night (USD)VRBO
Charming House in Oxford, MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This adorable updated bungalow is the perfect home base for your trip to the quaint waterfront town of Oxford! Guests w ...
From $472 per night (USD)VRBO
From $189 per night (USD)VRBO
Tred Avon Tidehouse 2BR Downtown Oxford Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Oxford, Maryland is a charming waterfront town on the Tred Avon River known for its maritime history, scenic views, and ...
From $189 per night (USD)VRBO
From $262 per night (USD)Expedia
Vintage Pet-Friendly Cottage | Tilghman Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to The Hootenanny, a charming pet-friendly vintage cottage nestled in the heart of Tilghman Island. Tho ...
From $262 per night (USD)Expedia