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

Filter

Popular Areas

From $1280 per night (USD)
VRBO
Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings **IMPORTA ...
From $1280 per night (USD)
VRBO
From $611 per night (USD)
VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
STRN-23-22 BOOK WITH US AND RECEIVE A FREE BUSCHEL OF CRABS! Come enjoy the quaintness of Claiborne, MD, just 5 minutes ...
From $611 per night (USD)
VRBO
From $1007 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 $1007 per night (USD)
VRBO
From $768 per night (USD)
VRBO
St. Michael's Premier In-Town Rental with heated pool.
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 $768 per night (USD)
VRBO
From $886 per night (USD)
VRBO
September Splender! Waterfront ,Pool, Dock, Hot Tub.A Luxury VIP Vacation Rental
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 and a privat ...
From $886 per night (USD)
VRBO
From $270 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 $270 per night (USD)
VRBO
From $302 per night (USD)
VRBO
The Middle Point Cabin in Saint Michaels
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Our Talbot County Short Term Rental License Number is: ST-634-EIN 2019 Talbot County requires a minimum 3 night booking ...
From $302 per night (USD)
VRBO
From $521 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 $521 per night (USD)
VRBO
From $2452 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 $2452 per night (USD)
VRBO
Click For Pricing
Expedia
The Yellow Victorian in Historic Cambridge – Walk to Everything!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The best kept little secret! Historic Cambridge, less than 2hours from DC/VA and 1 hour to the beach. House is located j ...
Click For Pricing
Expedia
From $480 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 $480 per night (USD)
VRBO
From $301 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 $301 per night (USD)
VRBO
From $759 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 shore ...
From $759 per night (USD)
VRBO
From $509 per night (USD)
VRBO
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
ST-605-JOH Upon arrival you realize this is the Eastern Shore Experience you have been looking for......A gated garden ...
From $509 per night (USD)
VRBO
From $825 per night (USD)
VRBO
Tuckaway Cove. Book your fall get away now. New kitchen 2025
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Tucked away on a beautiful, quiet cove off the Miles River, with a large yard for playing, a private pool & dock, & kaya ...
From $825 per night (USD)
VRBO
$ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY$
From $1406 per night (USD)
Expedia
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET 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 $1406 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Classic Eastern Shore Waterfront Manor House - ST-936
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Quintessential Eastern Shore experience on 30 acres 1.5 miles from downtown St. Michaels. Original house dates to the e ...
From $1535 per night (USD)
VRBO
From $356 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 $356 per night (USD)
VRBO
From $726 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 $726 per night (USD)
VRBO
From $314 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 $314 per night (USD)
VRBO
From $885 per night (USD)
VRBO
Private Retreat with HUGE Water Views!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Wonderful large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), th ...
From $885 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $549 per night (USD)
VRBO
From $363 per night (USD)
VRBO
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 $363 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Cottage on Cabin Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The cottage is the perfect place for a couple's get away. The views of Cabin Creek are stunning. You will enjoy beautifu ...
From $272 per night (USD)
VRBO
From $1048 per night (USD)
VRBO
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
TREMEZZO STAY - RANCH AT ROYAL OAK Our properties are owned, managed, and hosted by us. We deliver personally hosted lu ...
From $1048 per night (USD)
VRBO
From $878 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 $878 per night (USD)
VRBO
From $425 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 $425 per night (USD)
VRBO
From $509 per night (USD)
VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated one story home directly on the water. Gorgeous hickory floors. Open layout for entertaining. Din ...
From $509 per night (USD)
VRBO
From $1377 per night (USD)
VRBO
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
Bedrooms:
4
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 $1377 per night (USD)
VRBO
From $407 per night (USD)
Expedia
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 $407 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Historic Renovated Jackrabbit Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $432 per night (USD)
VRBO
From $885 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 $885 per night (USD)
Expedia
From $855 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 $855 per night (USD)
VRBO
From $1127 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 $1127 per night (USD)
Expedia
From $1023 per night (USD)
VRBO
Breathtaking Waterfront Estate
Bedrooms:
4
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 $1023 per night (USD)
VRBO
From $512 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 $512 per night (USD)
VRBO
From $753 per night (USD)
VRBO
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Escape to our 4-bedroom vacation home in Easton, just a 5-7 minute drive from the renowned St. Michaels. Immerse yoursel ...
From $753 per night (USD)
VRBO
From $1451 per night (USD)
Expedia
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 $1451 per night (USD)
Expedia
From $826 per night (USD)
VRBO
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Step into history without sacrificing modern comforts. Combsberry is a 1730 waterfront estate nestled on 30 pri ...
From $826 per night (USD)
VRBO
From $771 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $771 per night (USD)
VRBO
$Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30$
From $631 per night (USD)
VRBO
Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #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 $631 per night (USD)
VRBO
From $918 per night (USD)
Expedia
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Bedrooms:
2
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 $918 per night (USD)
Expedia
Click For Pricing
VRBO
Historic 1918 House 1/2 Block from the Choptank River
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
Click For Pricing
VRBO
From $1540 per night (USD)
VRBO
Beautiful Tidewater home between Easton & ST Michaels!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Quintessential charming Eastern Shore waterfront home stocked with all the amenities to make your stay stress free and ...
From $1540 per night (USD)
VRBO
From $340 per night (USD)
VRBO
Little Creek Hideaway - Privacy and Perfect Family Getaway.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Come relax at Little Creek Hideaway, the perfect family getaway during any season. Located just 10 minutes from Easton, ...
From $340 per night (USD)
VRBO
Click For Pricing
Expedia
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully decorated Harris Creek waterfront home is waiting for you! With plenty of room for multiple families to ...
Click For Pricing
Expedia
From $1325 per night (USD)
VRBO
Gorgeous Waterfront
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beautiful waterfront home - well furnished large open house, great amenities including pool, game room and gym, Sonos so ...
From $1325 per night (USD)
VRBO
From $307 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 $307 per night (USD)
VRBO
From $856 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 $856 per night (USD)
VRBO
From $1515 per night (USD)
Expedia
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 $1515 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
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 $1000 per night (USD)
Expedia
$Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n$
From $358 per night (USD)
Expedia
Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FALL SPECIAL BOOK 3 NIGHTS AND GET A 1/2 BUSHEL OF CRABS FREE Located on a private 27 acre estate is nestled a mere 200 ...
From $358 per night (USD)
Expedia
From $534 per night (USD)
Expedia
Waterfront Home on Chesapeake Bay with Dock, Bikes & Sunset Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Escape to the quiet charm of Tilghman Island at this bright, open-concept waterfront home. Located directly on ...
From $534 per night (USD)
Expedia
From $634 per night (USD)
VRBO
AUGUST Bookings, 15% Off. Near St.Michaels/Easton Waterfront, Dock,Hot Tub.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Another Luxury VIP Vacation Rental Property on the eastern shore. License # STRN-22-25 Stay at this comfortable propert ...
From $634 per night (USD)
VRBO
From $1708 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 $1708 per night (USD)
Expedia
From $1044 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
Eastern Shore Vacation Rentals presents The Water House. Beautifully appointed with artwork and antiques, The Water Hous ...
From $1044 per night (USD)
VRBO
From $656 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 $656 per night (USD)
Expedia
From $707 per night (USD)
VRBO
Tilghman | Pool | Private Dock | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Talbot County STR License# STRN-22-1 Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and ...
From $707 per night (USD)
VRBO
From $709 per night (USD)
Expedia
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 $709 per night (USD)
Expedia
From $256 per night (USD)
VRBO
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 $256 per night (USD)
VRBO
From $1197 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 $1197 per night (USD)
VRBO
From $751 per night (USD)
VRBO
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 $751 per night (USD)
VRBO
From $461 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 $461 per night (USD)
VRBO
From $490 per night (USD)
VRBO
Downtown Oxford | Charming | Pet Friendly | Bikes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming Cottage in the heart of Oxford, within walking distance to all our favorite Oxford things! We call this circa 1 ...
From $490 per night (USD)
VRBO
From $591 per night (USD)
Expedia
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 ...
From $591 per night (USD)
Expedia
From $297 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 $297 per night (USD)
VRBO
From $757 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 $757 per night (USD)
Expedia
From $829 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 crabbi ...
From $829 per night (USD)
VRBO
From $1069 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 $1069 per night (USD)
VRBO
From $737 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 $737 per night (USD)
VRBO
From $363 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 $363 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the h ...
From $296 per night (USD)
VRBO
From $1101 per night (USD)
Expedia
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 $1101 per night (USD)
Expedia
From $336 per night (USD)
VRBO
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 $336 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to your private escape on Tilghman Island — a waterfront home with panoramic water views, a dock for b ...
From $442 per night (USD)
Expedia
From $557 per night (USD)
VRBO
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $557 per night (USD)
VRBO
From $1181 per night (USD)
VRBO
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 $1181 per night (USD)
VRBO
From $401 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 $401 per night (USD)
VRBO
From $648 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 $648 per night (USD)
Expedia
From $358 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 $358 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Cottage downtown on a quiet street
Bedrooms:
1
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 $296 per night (USD)
Expedia
From $2299 per night (USD)
VRBO
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on ...
From $2299 per night (USD)
VRBO
From $285 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 $285 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 Pricing
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
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 Pricing
VRBO
From $541 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is fully visi ...
From $541 per night (USD)
VRBO
From $1312 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 $1312 per night (USD)
VRBO
From $681 per night (USD)
Expedia
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 $681 per night (USD)
Expedia
From $275 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 renovated salt-box style home on the Choptank River of Maryland's Eastern Shore, ...
From $275 per night (USD)
VRBO
From $528 per night (USD)
Expedia
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 $528 per night (USD)
Expedia
From $1046 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 $1046 per night (USD)
VRBO
From $988 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 $988 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Choptank River Beach Home w/ Pier in Cambridge!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $683 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy “the good old days” in style! This exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior an ...
From $661 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Stunning views at 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 $396 per night (USD)
VRBO
From $248 per night (USD)
VRBO
Perfect Waterview Cottage - St. Michaels Getaway
Bedrooms:
1
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 $322 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 $322 per night (USD)
VRBO
From $215 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 $215 per night (USD)
Expedia

Search Your Destination Now!

Talbot Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 237 Rentals