St. Michaels Vacation Rentals
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
37 rentals in St. Michaels.
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
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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
Walk to Everything House
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
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
More info
Check in
Check out
As seen on
Chic Flat with King Bed & Fireplace
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
Beautiful Waterfront Home w/ Pool In St. Michaels
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
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
More info
Check in
Check out
As seen on
Seasonal Rental: Artisan designed 3 bedroom home.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Warm Up Here! Your Winter Getaway Awaits
More info
Check in
Check out
As seen on
Grace Cottage, Saint Michaels Walk to everything!
More info
Check in
Check out
As seen on
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
More info
Check in
Check out
As seen on
Unwind at this Waterfront Retreat
More info
Check in
Check out
As seen on
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
More info
Check in
Check out
As seen on
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
More info
Check in
Check out
As seen on
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
More info
Check in
Check out
As seen on
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
More info
Check in
Check out
As seen on
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
More info
Check in
Check out
As seen on
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
More info
Check in
Check out
As seen on
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
More info
Check in
Check out
As seen on
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
More info
Check in
Check out
As seen on
Classic Eastern Shore Waterfront Manor House - ST-936
More info
Check in
Check out
As seen on
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
More info
Check in
Check out
As seen on
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
2BR Waterfront Family Escape
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Couples Retreat, 2 King Bedrooms!
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental
More info
Check in
Check out
As seen on
Bateau Cabin one of three Cove Cabins in St Michaels
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Celebrate the Season! Cozy Waterfront Escape
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Showing results 1-37 of 37
Frequently Asked Questions about St. Michaels
- Yes, here are some popular vacation rentals in St. Michaels that have a pool:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Delightful Close to town
- Yes, here are some popular vacation rentals in St. Michaels that have internet access:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Delightful Close to town
- Some of the most popular kid friendly rentals in St. Michaels are:
- Stay in the HEART of Saint Michaels!
- Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
- Delightful Close to town
St. Michaels TourismSt. Michaels HotelsSt. Michaels Bed and BreakfastSt. Michaels Vacation RentalsFlights to St. MichaelsSt. Michaels RestaurantsThings to Do in St. MichaelsSt. Michaels Travel ForumSt. Michaels PhotosSt. Michaels MapSt. Michaels Travel Guide
All St. Michaels HotelsSt. Michaels Hotel DealsLast Minute Hotels in St. Michaels
Things to DoRestaurantsFlightsTravel StoriesCruisesRental CarsSt. Michaels CampgroundsSt. Michaels Business HotelsRomantic Hotels in St. MichaelsSt. Michaels Spa ResortsSt. Michaels ResortsSt. Michaels Green HotelsSt. Michaels Family HotelsSt. Michaels Luxury Hotels
St. Michaels Hotels with Outdoor PoolSt. Michaels Non-Smoking HotelsSt. Michaels Hotels with ConciergeSt. Michaels Hotels with GymSt. Michaels Hotels with FireplacesSt. Michaels Accessible HotelsSt. Michaels Hotels with Air ConditioningSt. Michaels Hotels with a ViewSt. Michaels Hotels with Banquet hallSt. Michaels Hotels with Bridal Suite