Holiday Rentals in Talbot County
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
170 rentals in Talbot County.
Relaxing Waterfront Cottage Near St Michaels, Maryland
More info
Check-in
Check-out
As seen on
Stay in the HEART of Saint Michaels!
More info
Check-in
Check-out
As seen on
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
More info
Check-in
Check-out
As seen on
Delightful Close to town
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Breathtaking Waterfront Estate
More info
Check-in
Check-out
As seen on
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
More info
Check-in
Check-out
As seen on
Hurry, reserve your stay for Summer & Fall of 2025 STR #22-30
More info
Check-in
Check-out
As seen on
St. Michaels Waterfront Home
More info
Check-in
Check-out
As seen on
Walk to Everything House
More info
Check-in
Check-out
As seen on
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
More info
Check-in
Check-out
As seen on
Cottage at Goose Neck Point
More info
Check-in
Check-out
As seen on
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
More info
Check-in
Check-out
As seen on
Dollhouse in Central Historic St Michaels
More info
Check-in
Check-out
As seen on
St. Michael's Premier In-Town Rental with heated pool - Pool is open!
More info
Check-in
Check-out
As seen on
Chase Away the Chill with Our Winter Stay Specials!
More info
Check-in
Check-out
As seen on
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
More info
Check-in
Check-out
As seen on
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
More info
Check-in
Check-out
As seen on
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
More info
Check-in
Check-out
As seen on
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
More info
Check-in
Check-out
As seen on
Historic Oxford Waterfront Estate
More info
Check-in
Check-out
As seen on
Luxurious waterfront home - Cèilidh
More info
Check-in
Check-out
As seen on
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
More info
Check-in
Check-out
As seen on
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private
More info
Check-in
Check-out
As seen on
Eastern Shore Getaway Near St. Michaels
More info
Check-in
Check-out
As seen on
Chic Flat with King Bed & Fireplace
More info
Check-in
Check-out
As seen on
Waterfront Property, kayaks, private dock, near town
More info
Check-in
Check-out
As seen on
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
More info
Check-in
Check-out
As seen on
Bay breezes, winter sunsets, heated luxury spa.
More info
Check-in
Check-out
As seen on
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
More info
Check-in
Check-out
As seen on
Harbor View Suite
More info
Check-in
Check-out
As seen on
Downtown Oxford | Charming | Pet Friendly | Bikes
More info
Check-in
Check-out
As seen on
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
More info
Check-in
Check-out
As seen on
Thorneton Point Estate
More info
Check-in
Check-out
As seen on
Perfect Waterview Cottage - St. Michaels Getaway
More info
Check-in
Check-out
As seen on
Beautiful Waterfront Home w/ Pool In St. Michaels
More info
Check-in
Check-out
As seen on
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
More info
Check-in
Check-out
As seen on
Downtown St. Michaels | Bikes | Kayaks | Private Pier
More info
Check-in
Check-out
As seen on
Quaint Tilghman Island home
More info
Check-in
Check-out
As seen on
Newly Renovated Guest House located in Oxford MD
More info
Check-in
Check-out
As seen on
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
More info
Check-in
Check-out
As seen on
5 bedroom Bed and Breakfast on the Choptank River
More info
Check-in
Check-out
As seen on
4-Bedroom Retreat: Modern, Pet-Friendly
More info
Check-in
Check-out
As seen on
The B&B of Anchorage - Skipjack
More info
Check-in
Check-out
As seen on
The Anchorage B&B - The Bounty
More info
Check-in
Check-out
As seen on
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
More info
Check-in
Check-out
As seen on
Relax or Play on the Choptank River!
More info
Check-in
Check-out
As seen on
Adorable two-bedroom retreat close to Easton, Denton, Centreville
More info
Check-in
Check-out
As seen on
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!
More info
Check-in
Check-out
As seen on
Waterfront Getaway on the Choptank River
More info
Check-in
Check-out
As seen on
Seasonal Rental: Artisan designed 3 bedroom home.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 170
Frequently Asked Questions about Talbot County
- Yes, here are some popular holiday rentals in Talbot County that have a pool:
- Relaxing Waterfront Cottage Near St Michaels, Maryland
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Yes, here are some popular holiday rentals in Talbot County that have internet access:
- Relaxing Waterfront Cottage Near St Michaels, Maryland
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- The best pet friendly rentals in Talbot County are:
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Breathtaking Waterfront Estate
- John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
- Some of the most popular kid friendly rentals in Talbot County are:
- Relaxing Waterfront Cottage Near St Michaels, Maryland
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Talbot County TourismTalbot County HotelsTalbot County Guest HouseTalbot County Holiday HomesTalbot County FlightsTalbot County RestaurantsTalbot County AttractionsTalbot County Travel ForumTalbot County MapTalbot County Visitors Guide
All Talbot County HotelsTalbot County Hotel Deals
Things to DoRestaurantsFlightsHoliday homesTravel StoriesCruisesCar Hire