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Saint Michaels, MD place to stay
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76 Lodgings in Saint Michaels, MD

Best Saint Michaels, MD lodging with a pool

Among the 76 accommodations in Saint Michaels, MD, here are the 4 best ones with a pool

Waterfront - 3 Luxury Bdrms W/ Outside Pool & Spa - Saint Michaels, MD
9.7 15 reviews

Waterfront - 3 Luxury Bdrms W/ Outside Pool & Spa

apartment, Tilghman Island
This charming apartment is located on Tilghman Island in Talbot County, offering stunning water views and easy access to various water activities. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to six guests. The property offers a range of amenities including a swimming pool, Jacuzzi, garden, fitness centre, and parking, as well as a fully equipped kitchen and air conditioning.
Waterfront Farmhouse Retreat On 18 Acres, Pool - Saint Michaels, MD
10 18 reviews

Waterfront Farmhouse Retreat On 18 Acres, Pool

apartment, Oxford
This 18-acre farm is situated on the waterfront, just a short drive from both Easton and Saint Michaels.
This eight-bedroom farmhouse provides a peaceful retreat for up to 16 guests, featuring a swimming pool, gym, tennis court, kayaks, fishing equipment, a fire pit, an ice cream shop, a library, and a petting zoo.
Baydream Believer - Saint Michaels, MD
10 1 review

Baydream Believer

house, Tilghman Island
Baydream Believer, a five-bedroom house in Saint Michaels, Maryland, is situated approximately 24 kilometres from the Academy of the Arts and 106 kilometres from Salisbury-Ocean City Wicomico Regional Airport, offering convenient access to Tilghman Island.
This 465-square-metre property sleeps up to 15 guests and boasts a private pool, Jacuzzi, tennis court, and fully equipped kitchen; additional features include a terrace, garden, and free Wi-Fi.
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.

Best family friendly Saint Michaels, MD lodging

Among the 76 accommodations in Saint Michaels, MD, here are the 4 best for families

Cozy, Family-friendly Log Cabin-st. Michaels - Saint Michaels, MD
10 17 reviews

Cozy, Family-friendly Log Cabin-st. Michaels

apartment, Oxford
This four-bedroom log cabin, sleeping eight, is situated in Talbot County, Maryland, approximately 5 kilometres from the historic town of St. Michaels.
The self-catering lodge boasts two bathrooms, a kitchen, air conditioning, internet access, parking, and pet-friendly accommodation; enjoy s'mores around a fire pit, subject to a three-night minimum stay and no-party policy.
Private&cozy/3br+2ba/1mi To Town - Saint Michaels, MD
9.9 95 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.
Miles Rest | An Esvr Property - Saint Michaels, MD
8.7 3 reviews

Miles Rest | An Esvr Property

apartment, Easton
This Easton, Maryland waterfront house boasts 230 feet of Miles River shoreline on a 0.9 hectare lot, offering expansive views.
Sleeping up to 10 guests, this five-bedroom, 3.5-bathroom property features a private pool, hot tub, and updated kitchen, plus linens, towels and essential supplies.
Moofy's Farmhouse: Main Lodge ; Private Waterfront - Saint Michaels, MD
10 9 reviews

Moofy's Farmhouse: Main Lodge ; Private Waterfront

apartment, Oxford
This waterfront lodge is situated on the eastern shore, just a short distance from both Easton and Saint Michaels, offering a peaceful retreat away from the hustle and bustle of Oxford. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This spacious dwelling has 25 bedrooms and 20 bathrooms, comfortably accommodating up to 16 guests. The lodge offers a range of amenities and activities, including a swimming pool, tennis court, gym, library, fire pit, ice cream shop, gardens, a petting zoo, and an art barn.

Frequently asked questions about accommodations in Saint Michaels, MD

  • What outdoor activities can visitors enjoy in and around Saint Michaels, MD?

    Saint Michaels is a great place for outdoor activities. You can go kayaking or paddleboarding on the Miles River, or take a boat tour to see the local wildlife. There are also plenty of walking and cycling trails in the area, including the scenic Chesapeake Bay Trail.
  • When is the ideal time to plan a trip to Saint Michaels, MD?

    Spring and autumn are the best times to visit Saint Michaels, when the weather is mild and the crowds are smaller. You can enjoy the beautiful scenery without the summer heat and humidity. If you're looking for a more lively atmosphere, you could visit in the summer, but be prepared for larger crowds and higher prices.
  • What are the best walking or cycling routes in Saint Michaels, MD?

    For a scenic walk, try the boardwalk along the Miles River. It's a lovely spot to enjoy the views and watch the boats go by. If you're looking for a longer ride, the Chesapeake Bay Trail is a great option, with over 300km of paved trails that wind through the countryside.
  • What nearby towns or cities can be explored from Saint Michaels, MD?

    If you're looking to explore the surrounding area, Easton is a charming town about 20 minutes away. You can also visit Annapolis, the state capital, which is about an hour's drive away. For a day trip, you could even head to Ocean City, a popular beach resort on the Atlantic coast, about 1.5 hours away.
  • What amenities can travelers expect from accommodations in Saint Michaels, MD?

    Saint Michaels offers a range of accommodation options, from charming bed and breakfasts to luxury hotels. Many accommodations have amenities like swimming pools, restaurants, and boat docks. You can also find plenty of vacation rentals, which are a great option for families or groups.

Popular destinations

Best Saint Michaels, MD accommodations with a balcony

Apartment ∙ 1 Bedroom ∙ 4 Guests - Saint Michaels, MD
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Easton
This one-bedroom flat offers an ideal base in downtown Easton, just 100 meters from the harbour, local shops, and acclaimed restaurants.
This second-floor apartment accommodates up to four guests with a king-sized bedroom and a pull-out sofa, featuring a fully equipped kitchen with high-end appliances, air conditioning, a gas fireplace, and driveway parking for two vehicles.
Saint Michaels Summer Retreat With Pool & Hot Tub - Saint Michaels, MD
10 13 reviews

Saint Michaels Summer Retreat With Pool & Hot Tub

apartment, Tilghman Island
This waterfront apartment is located in McDaniel, just 3km from the town of St. Michaels, offering a peaceful retreat while still being close to local attractions. The apartment is ideal for families or groups of friends, with 3 bedrooms and 4 bathrooms, comfortably accommodating up to 6 guests.
The apartment boasts a modern and spacious interior with a fully equipped kitchen, a private swimming pool, and a jacuzzi, perfect for relaxing after a day exploring the island. Guests can also enjoy stunning views from the terrace or balcony, and take advantage of the shared dock for swimming, kayaking, or simply soaking up the sun.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 134 reviews

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
10 10 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.

Best Saint Michaels, MD accommodations with a kitchen

Bayside The Point - Saint Michaels, MD
No reviews

Bayside The Point

house, Oxford
This spacious six-bedroom property, perfect for large groups, is situated near Royal Oak, Maryland, approximately 13.7 kilometres from the Academy of the Arts and 95 kilometres from Baltimore-Washington International Airport; note that this property is not located in Oxford.
The 224-square-metre house boasts four bathrooms, a private swimming pool, jacuzzi, free Wi-Fi, and parking, comfortably accommodating up to 23 guests.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

house, Trappe
This substantial Trappe dwelling is located within the district, offering straightforward access to the Academy of the Arts, 8.9 kilometres away, and within driving distance of Federalsburg Marina, 40.2 kilometres away, and the Chesapeake Exploration Centre, 48.3 kilometres away.
This property spans 204 square metres and features four bedrooms, three bathrooms, and accommodates up to 15 guests, with amenities including air conditioning, WiFi, a private swimming pool, a terrace, and on-site parking, alongside a strict no-party policy.
Waterfront Estate - Riverslie On The Miles River - Saint Michaels, MD
9.6 27 reviews

Waterfront Estate - Riverslie On The Miles River

house, Easton
This secluded farmhouse is located 18 kilometres outside of Easton and 15 kilometres from St. Michaels, offering a peaceful retreat surrounded by water and 11 acres of private land. The farmhouse is perfect for a family getaway or a group of friends looking to enjoy a tranquil escape.
The five-bedroom, four-bathroom farmhouse can accommodate up to 10 guests, offering plenty of space for everyone to relax and enjoy the amenities. Guests can take advantage of the private pool, the fully-equipped kitchen, the spacious living areas, and the two docks for crabbing and fishing.
Charming Waterfront Cottage Retreat Near St. Michaels - Saint Michaels, MD
10 11 reviews

Charming Waterfront Cottage Retreat Near St. Michaels

cottage, Tilghman Island
This waterfront holiday home in Bozman, Maryland, is located minutes from the historic town of St. Michaels and offers easy access to Tilghman Island attractions.
The 74-square-metre (800 sq ft) property boasts one bedroom, two bathrooms, sleeps two guests, and includes a gourmet kitchen, private dock, and access to kayaking and fishing in the nearby nature preserve and back cove.
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