
Talbot Area Rentals

- From $912 per night (USD)
VRBO
Stunning Waterfront Escape with New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...
From $912 per night (USD)VRBO
- From $751 per night (USD)
VRBO
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4th of July Availability!! If you enjoy the old-fashioned fireworks, ice cream and BBQ picnic- Independence day celebra ...
From $751 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Time Stands Still At the Dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the ...
From $553 per night (USD)VRBO
- From $412 per night (USD)
Expedia
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Old School Charm Meets New School Living! This charming 3BR, 2BA duplex vacation home within walking distance from Down ...
From $412 per night (USD)Expedia
- From $1397 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your dream retreat, nestled in a serene cove that feels like a page from a fairytale. This enchanting waterfr ...
From $1397 per night (USD)VRBO
- From $1156 per night (USD)
Expedia
Short drive to Downtown Cambridge | Private Dock | Guest House
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
Bucolic and Serene NEW POOL COMING SOON! This charming 6BR, 3BA Victorian waterfront vacation home complimented by a 1B ...
From $1156 per night (USD)Expedia
- From $394 per night (USD)
VRBO
Charming Waterfront Cottage Retreat near St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the ultimate getaway at this stunning waterfront cottage on Maryland’s picturesque Eastern Shore, nestled minut ...
From $394 per night (USD)VRBO
- Click For Pricing
Expedia
Charming 1-bedroom cottage in downtown Saint Michaels
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...
Click For PricingExpedia
- From $157 per night (USD)
VRBO
Cambridge Apt in Walkable Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $157 per night (USD)VRBO
- From $1063 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
A breathtaking waterfront estate that seamlessly combines luxury and nature. Welcome to Miles End, a breathtaking water ...
From $1063 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Charming 1-bedroom cottage on the water, minutes from St Michaels MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
King Size Comfort. The ambience of each cottage is one of relaxed comfort. Fashionable cottage décor is enhanced with co ...
From $188 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Waterfront cottage, 1 bd 1 bath, Perfect for your next getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The perfect couples’ getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhan ...
From $245 per night (USD)VRBO
- From $277 per night (USD)
VRBO
Charming 2-bedroom cottage, waterfront, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect, small family, getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is ...
From $277 per night (USD)VRBO
- From $972 per night (USD)
Expedia
Stunning Chesapeake Waterfront Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. ...
From $972 per night (USD)Expedia
- From $445 per night (USD)
VRBO
The Farm House at Hunting Creek
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the charm of this stunning, gated estate carriage house, nestled on 80 acres of breathtaking land. With panor ...
From $445 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Walk to Dtwn: Waterfront Eastern Shore Townhome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $419 per night (USD)Expedia
- From $964 per night (USD)
VRBO
Waterfront Home with Pool & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Wake up to waterfront living - toss crab pot off the dock in the morning & steam your catch for dinner. Spend a ...
From $964 per night (USD)VRBO
- Click For Pricing
Expedia
Spacious Family Getaway – Summer Ready!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Pack your bags and gather the crew—this bright and welcoming 4-bedroom, 4.5-bath home is everything a summer ge ...
Click For PricingExpedia
- From $276 per night (USD)
VRBO
Cottage #1 Lighthouse First Cottage down driveway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
OPEN March 25th until October 31st each year. No 1 is First cottage down drive has a full Kitchen, dining table, queen s ...
From $276 per night (USD)VRBO
- From $780 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 $780 per night (USD)Expedia
- From $1096 per night (USD)
VRBO
Escape to The Beach House - Your Waterfront Oasis Awaits!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Discover paradise at The Beach House, a stunning waterfront rental offered by Tidewater Vacations. Nestled along the ser ...
From $1096 per night (USD)VRBO
- From $102 per night (USD)
Expedia
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Wye Mills is waiting for you at this awesome 1-bedroom cottage. With WiFi, heating, a washing machine, and more, guests ...
From $102 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Cottage #4 Chesapeake Blue down the drive way.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $294 per night (USD)VRBO
- From $294 per night (USD)
VRBO
#3 Mallard Cottage (located 3rd down drive)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $294 per night (USD)VRBO
- From $236 per night (USD)
VRBO
Cottage #9 Stateroom located under main home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
OPEN March 25th to Nov 1st. Each year. State Room has no kitchen is located under main house, consist of small dining ta ...
From $236 per night (USD)VRBO
- From $319 per night (USD)
Expedia
Cottage #6 Wild Goose on the left of Main House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
OPEN March 25th to Nov 1st. No6) Wild goose located to left of main house, consist of full Kitchen, dining table, queen ...
From $319 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Charming Well Priced Home Minutes From St Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Traveling to the shore for a friends & family event? Looking for a cozy well priced option? Centrally located b ...
From $251 per night (USD)VRBO
- From $1289 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Take control of your next vacation. Escape to your dream waterfront vacation at this extraordinary 5-bedroom estate on ...
From $1289 per night (USD)Expedia
- From $393 per night (USD)
VRBO
Aurora Blue - A Stylish Experience \n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $393 per night (USD)VRBO
- From $578 per night (USD)
Expedia
Charming, Waterfront 2-bedroom house Royal Oak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your cozy getaway awaits in Royal Oak at this brilliant house. With 2 bedrooms guests can unwind in comfort. The proper ...
From $578 per night (USD)Expedia
- From $978 per night (USD)
VRBO
Downtown Oxford | Private Beach | Private Pool | Luxury
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighbo ...
From $978 per night (USD)VRBO
- From $880 per night (USD)
Expedia
Secluded 1870s farmhouse full of historic charm + breathtaking waterfront views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This secluded 1870s farmhouse is full of historic charm and surrounded by natural beauty. Take in breathtaking views of ...
From $880 per night (USD)Expedia
- From $377 per night (USD)
VRBO
St. Michaels Escape – Walk to Town!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Easy walking and biking distance to the heart of St. Michaels. Enjoy shops, restaurants, and waterfront charm j ...
From $377 per night (USD)VRBO
- From $346 per night (USD)
Expedia
Charming 3-bedroom in Village of Claiborne \nwith continental breakfast STR24-33
- 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 $346 per night (USD)Expedia
- From $1261 per night (USD)
VRBO
Waterfront Farmhouse | Pool, Dock, Pets Welcome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Imagine waking up to the gentle lapping of water on a quiet inlet, just a short drive from the charming streets ...
From $1261 per night (USD)VRBO
- From $384 per night (USD)
Expedia
#2 Egret Cottage Harris Cove
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax with the whole family at this peaceful place to stay. Great Sunset and Sunrises, located on Harris Creek, each cot ...
From $384 per night (USD)Expedia
- From $315 per night (USD)
VRBO
Cottage #5 White Swan At Water with Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $315 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Cottage #8 Herons Nest Lg 2 rooms Under Main House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $371 per night (USD)VRBO
- From $404 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 $404 per night (USD)VRBO
- From $469 per night (USD)
Expedia
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 $469 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Waterfront Home w/ Hot Tub in Bozman Village!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5 ...
From $340 per night (USD)VRBO