Find short term rentals in Saint Michaels, MD at the best prices

52 available short term rental offers

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Saint Michaels, MD short term rentals
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Best Short term and Weekly rentals in Saint Michaels, MD

Best family friendly Saint Michaels, MD Short term rentals

Among the 52 accommodations in Saint Michaels, MD, here are the 4 best family friendly rentals

Private&cozy/3br+2ba/1mi To Town - Saint Michaels, MD
9.9 88 reviews

Private&cozy/3br+2ba/1mi To Town

apartment, Tilghman Island
This charming holiday home is located just under 1.6km from the centre of Saint Michaels, a historic town on Maryland's Eastern Shore, offering a peaceful escape with easy access to local attractions. The property has received excellent ratings for location, cleanliness and overall user experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The fully equipped kitchen, spacious living area, and private garden with a patio offer a comfortable and relaxing stay, while the proximity to Tilghman Island (around 24km away) makes it a perfect base for exploring the region.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.6 18 reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

apartment, Trappe
This Trappe holiday home, situated within 9.6km of the Third Haven Friends Meeting House, Academy Art Museum, and Academy of the Arts, offers convenient access to local attractions and amenities.
This five-bedroom, three-bathroom property boasts 204 square metres of living space, including a private pool, fully equipped kitchen, and can comfortably accommodate eight guests.
Minutes From Downtown St. Michaels | Pool | Dock - Saint Michaels, MD
10 2 reviews

Minutes From Downtown St. Michaels | Pool | Dock

apartment, Tilghman Island
This stunning cedar Lindal home, situated near St. Michaels on Tilghman Island's Eastern Shore, offers breathtaking Broad Creek waterfront views and is a short drive from St. Michaels Museum and Avalon Theatre.
Sleeping up to six guests, this three-bedroom, three-bathroom property boasts a chef-inspired kitchen, private heated pool (seasonal, 15 May – 15 October), private dock, kayaks, paddleboards, and expansive entertainment areas including a wrap-around porch and propane fire pit.
Hummingbird Inn - Saint Michaels, MD
10 118 reviews

Hummingbird Inn

B&B, Easton
The Hummingbird Inn is located in Easton, just a short walk from the Academy of the Arts, making it a perfect base for exploring the town's cultural attractions. It has received excellent ratings for location, cleanliness, and overall user experience.
The inn offers a range of rooms, some with private bathrooms, spa baths, and other amenities. Guests can enjoy free parking, Wi-Fi, and bicycles, as well as a terrace, garden, spa, and fitness centre.

Best Saint Michaels, MD lodging with a balcony

Cozy, Family Friendly, Log Cabin-st. Michaels, Md - Saint Michaels, MD
9.8 10 reviews

Cozy, Family Friendly, Log Cabin-st. Michaels, Md

apartment, Oxford
This woodland lodge is located in Talbot County, just 4.8 kilometres from historic St. Michaels and 12.9 kilometres from Easton, offering a secluded setting overlooking a freshwater pond.
This family-friendly cabin accommodates up to eight guests with four bedrooms, two bathrooms, and features a fully equipped kitchen, air conditioning, a terrace, garden, and parking, with opportunities for wildlife observation and fishing on the pond.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
10 9 reviews

St. Michaels Escape | Pool, Hot Tub & Fire Pit

apartment, Tilghman Island
This waterfront flat on Porters Creek, Tilghman Island, offers direct water access and is located a mere few minutes from St. Michaels' restaurants, shops, and museums.
This property, accommodating up to six guests, boasts three bedrooms, two bathrooms, a private pool, hot tub, fire pit, and a private dock for fishing and crabbing.
Cozy 2-bedroom Cottage On Tilghman Island  Near Restaurants & Water Activities - Saint Michaels, MD
10 13 reviews

Cozy 2-bedroom Cottage On Tilghman Island Near Restaurants & Water Activities

apartment, Tilghman Island
This two-bedroom holiday home is situated on Tilghman Island, a short walk from the Tilghman Island Country Store and within easy driving distance of Knapp's Narrows Marina & Inn.
The self-catering property sleeps four, boasts a fully equipped kitchen including a dishwasher, air conditioning, and a garden, and is ideally located for exploring Back Creek Community Park and the Chesapeake Bay Maritime Museum.
Charming 3-bedroom  In Village Of Claiborne  Book 3 Nights Get 4th Free Strn26-6 - Saint Michaels, MD
10 1 review

Charming 3-bedroom In Village Of Claiborne Book 3 Nights Get 4th Free Strn26-6

apartment, Claiborne
This three-bedroom house in Claiborne, a short drive from St. Michaels, offers easy access to the Chesapeake Bay Maritime Museum and St. Michaels Museum, both within a few kilometres.
The property sleeps six, includes WiFi and air conditioning, and is close to the Phillips Wharf Environmental Center and Paul Reed Smith Guitars, providing a relaxing base for exploring Tilghman Island.

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Best Saint Michaels, MD lodging with a kitchen

Downtown Retreat With Bikes, Fire Pit & Kayaks - Saint Michaels, MD
10 26 reviews

Downtown Retreat With Bikes, Fire Pit & Kayaks

apartment, Easton
This two-bedroom flat in St. Michaels is located a few minutes' drive from the town centre, offering convenient access to shops, restaurants, breweries, and wineries.
This pet-friendly apartment accommodates four guests and features a modern open-plan living space, two en-suite bedrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, complimentary bikes, two kayaks, a fire pit, and a BBQ grill.
Riverview Retreat | An Esvr Property - Saint Michaels, MD
10 47 reviews

Riverview Retreat | An Esvr Property

apartment, Easton
This waterfront holiday home is situated in St. Michaels, a charming town just 16 kilometres from Easton, offering easy access to the Chesapeake Bay Maritime Museum and the St. Michaels Winery. The property enjoys excellent user, location and cleanliness ratings.
This three-bedroom property spans 203 square metres and comfortably accommodates six guests. Enjoy stunning views, a cosy fireplace, a fully equipped kitchen, a private garden, a tennis court and a spa, all within a smoke-free environment.
Grandview - Cottage 1a, King Bed, Pool, Bay, Wifi - Saint Michaels, MD
9.6 29 reviews

Grandview - Cottage 1a, King Bed, Pool, Bay, Wifi

apartment, Tilghman Island
This charming cottage on Tilghman Island is just a short distance from the Chesapeake Bay and the Tilghman Island Marina, making it an ideal base for exploring the area. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cottage has one bedroom and one bathroom, comfortably accommodating up to two guests. Amenities include a fully equipped kitchen, air conditioning, a fireplace, Wi-Fi, a TV, a screened porch, and access to a swimming pool, ensuring a relaxing and enjoyable stay.
Minutes From Downtown St. Michaels | Private Boat Ramp | Dock - Saint Michaels, MD
6.0 1 review

Minutes From Downtown St. Michaels | Private Boat Ramp | Dock

apartment, Tilghman Island
This waterfront property on Tilghman Island is located within 15km of Neavitt Park, Perry Cabin Park, and CL Open Field, and also within 15km of St Michaels Town Hall and Higgins Yacht Yard and Marina.
This three-bedroom, three-bathroom holiday home boasts 207 square metres of floor space, sleeps six guests, and includes a fully equipped kitchen, spa, free Wi-Fi, laundry facilities, and barbecue grills.

Best Saint Michaels, MD lodging with laundry available

Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
10 6 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton
This apartment in St. Michaels is situated a short walk from St. Michaels Marina and Higgins Yacht Yard and Marina, placing guests within 500 metres of the waterfront.
This three-bedroom accommodation for six guests offers a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and on-site parking, with Wi-Fi and a washer/dryer provided for convenience.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Saint Michaels, MD
9.8 207 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring the town's rich maritime history and vibrant culture. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The two-bedroom cottage spans 130 square metres and comfortably accommodates up to five guests. It offers a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.
One-level Waterfront Home W Beach And Bay Views - Saint Michaels, MD
10 2 reviews

One-level Waterfront Home W Beach And Bay Views

apartment, Stevensville
This waterfront flat in Stevensville offers direct access to a private sandy beach on the Chesapeake Bay, located 1.9 kilometres from Kentmorr Beach Bar and Marina and the Blue Heron Golf Course.
Sleeping up to six guests, this property boasts three bedrooms, two bathrooms, a full kitchen, air conditioning, a garden, parking for 3-4 cars, and high-speed internet.
Miles Aweigh - Saint Michaels, MD
9.9 295 reviews

Miles Aweigh

apartment, Easton
This yacht is situated on Long Haul Creek, less than 1.6 km from the charming town of St. Michaels. It has received excellent ratings for user experience, location, and cleanliness.
The yacht features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a garden, and parking.
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