Places to stay in Saint Michaels, MD

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Saint Michaels, MD place to stay
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76 Best places to stay in Saint Michaels, MD

Best Saint Michaels, MD lodgings with a pool

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

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.
Brand-new Pool! Waterfront Bozman Village Home - Saint Michaels, MD
No reviews

Brand-new Pool! Waterfront Bozman Village Home

house, Tilghman Island
This waterfront property in Bozman Village, Tilghman Island, is situated 26 kilometres from the Academy of the Arts and 109 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
This spacious 223 square metre holiday home accommodates up to 15 guests with four bedrooms and three bathrooms, featuring a brand-new outdoor swimming pool, a fully equipped kitchen, and a barbecue grill, all with free WiFi.
Minutes From Downtown Easton And St. Michaels | Pool - Saint Michaels, MD
10 5 reviews

Minutes From Downtown Easton And St. Michaels | Pool

apartment, Oxford
This five-bedroom, three-bathroom apartment is located in Easton, Talbot County, Maryland, a waterfront property on Edge Creek offering access to attractions such as St. Michaels and the Chesapeake Bay Maritime Museum; note that this is not in Oxford as initially stated.
This 255-square-metre (2744 square feet) holiday home boasts a private pool, dock, and ample amenities for up to ten guests, including a fully equipped kitchen and air conditioning.
Brand-new Pool! Waterfront Bozman Village Home - Saint Michaels, MD
9.8 9 reviews

Brand-new Pool! Waterfront Bozman Village Home

apartment, Tilghman Island
This holiday home on Harris Creek, 8 kilometres from St. Michaels and its Chesapeake Bay Maritime Museum, offers waterfront access ideal for fishing, crabbing, and water sports.
This spacious 223 square metre property accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a heated swimming pool, hot tub, private fishing dock, and bicycles, all set on extensive grounds with parking and a garden.

Best family friendly Saint Michaels, MD lodging

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

Waterfront | Pet Friendly & Close To St. Michaels - Saint Michaels, MD
9.5 8 reviews

Waterfront | Pet Friendly & Close To St. Michaels

house, Tilghman Island
This waterfront dwelling on Tilghman Island provides direct creek access for water activities, with the historic town of St. Michaels, known for its boutiques and galleries, a short 5-kilometre drive away.
This family-friendly property accommodates up to eight guests, offering four bedrooms, two bathrooms, a private swimming pool, a garden, parking, and dual living areas, alongside outdoor amenities like a dock and barbecue facilities.
Saint Michaels Waterfront Home - Saint Michaels, MD
9.9 72 reviews

Saint Michaels Waterfront Home

apartment, Easton
This waterfront apartment is just over the bridge entering St. Michaels, a short 7-kilometre drive from Easton and a mere 30-second walk from The Oaks Wedding Resort. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The apartment has two bedrooms, two bathrooms, and comfortably accommodates up to four guests. Enjoy stunning views, easy access to water activities, a garden, parking, and a fully equipped kitchen with a fridge.
Sailor Joe's | An Esvr Property - Saint Michaels, MD
No reviews

Sailor Joe's | An Esvr Property

apartment, Tilghman Island
This Sherwood holiday home in Talbot County, Maryland, boasts stunning 180-degree water views and is conveniently located near Tilghman Island's attractions, though precise distances aren't specified.
The newly renovated three-bedroom, three-bathroom property offers a spacious, open-plan layout sleeping six guests, complete with a chef-inspired kitchen, dishwasher, fridge, and provision of linens and towels; internet access is available, although speed may be slow.
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.

Frequently asked questions about accommodations in Saint Michaels, MD

  • How can travelers reach Saint Michaels, MD?

    You can easily reach Saint Michaels by car, it's about a 2-hour drive from Baltimore or Washington, D.C. There's also a small airport nearby, Easton Airport, for those who prefer to fly.
  • What are the best accommodations in Saint Michaels, MD?

    Among the accommodations in Saint Michaels, MD, St - Michaels Inn, The Wildset and St Michaels Harbour Inn - Marina And Spa are the most popular ones.

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

    There are loads of ways to enjoy the outdoors! You can go kayaking or paddleboarding on the Miles River, take a scenic bike ride along the Chesapeake Bay, or go fishing on the pier at the harbour.
  • What are the best accommodations with a pool in Saint Michaels, MD?

    St - Michaels Inn, St Michaels Harbour Inn - Marina And Spa and Inn At Perry Cabin are the best accommodations with a pool in Saint Michaels, MD.

  • When is the ideal time to plan a trip to Saint Michaels, MD?

    Spring and autumn are lovely times to visit, with pleasant temperatures and fewer crowds. Summer gets busy, but it's great for enjoying the beaches and water activities. You can even visit during the winter for a quieter experience.
  • What are the best accommodations with a jacuzzi in Saint Michaels, MD?

    The best accommodations with a jacuzzi in Saint Michaels, MD are Inn At Perry Cabin, Parsonage Inn Bed And Breakfast and Beautiful Waterfront Home W\/ Pool In St - Michaels.

  • What are the best walking or cycling routes in Saint Michaels, MD?

    The Saint Michaels Walking Trail is a great option for a leisurely stroll, and it's also perfect for cycling. You can also explore the scenic waterfront area, heading towards the harbour, for a beautiful walk.
  • What are the best accommodations for families and kids in Saint Michaels, MD?

  • What nearby towns or cities can be explored from Saint Michaels, MD?

    You can easily visit Easton, a charming town with a historic centre and plenty of shops and restaurants. It's about a 15-minute drive from Saint Michaels. You can also explore the Eastern Shore region, with its beautiful beaches and quaint towns.
  • What are the best pet friendly accommodations in Saint Michaels, MD?

    The best pet friendly accommodations in Saint Michaels, MD are St - Michaels Inn, The Wildset and St Michaels Harbour Inn - Marina And Spa.

  • What amenities can travelers expect from accommodations in Saint Michaels, MD?

    There are a range of accommodation options in Saint Michaels, from charming bed and breakfasts to comfortable hotels and resorts. Many places offer amenities like swimming pools, restaurants, and boat docks. It's a great place to relax and enjoy the beautiful surroundings.
  • What are the best accommodations with parking in Saint Michaels, MD?

    St - Michaels Inn, The Wildset and St Michaels Harbour Inn - Marina And Spa are the best accommodations with parking in Saint Michaels, MD.

Popular destinations

Best Saint Michaels, MD accommodations with a balcony

Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
10 7 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.
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.
Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
10 2 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton
This studio flat is located in the central district of St. Michaels, a mere 100 metres from its boutiques, seafood restaurants, and harbour, offering authentic historic charm with exposed wood beams and coastal décor.
This pet-friendly accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a private terrace, and dedicated parking, with keyless entry for convenience.
Downtown St. Michaels Studio  Walk To Waterfront, Dining & Shops - Saint Michaels, MD
10 41 reviews

Downtown St. Michaels Studio Walk To Waterfront, Dining & Shops

studio, Easton
This St. Michaels apartment, a short distance from Muskrat Park and St Mary's Square, offers easy access to St. Michaels Museum and St. Michaels Winery, all within a 5-minute radius (approximately 0.8km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen with dishwasher, private balcony, parking, and Wi-Fi; enjoy nearby attractions such as the St Mary's Square Museum.

Best Saint Michaels, MD accommodations with a kitchen

3-bedroom Historic Vacation Home Newly Renovated In The Middle Of Oxford Md. - Saint Michaels, MD
No reviews

3-bedroom Historic Vacation Home Newly Renovated In The Middle Of Oxford Md.

apartment, Oxford
This Oxford holiday home is situated within a 15-minute walk of the Oxford Museum and Play Ball Dog Park, and within 20 km of The Third Haven Friends Meeting House and the Academy Art Museum.
Sleeping six guests, this three-bedroom, three-bathroom property boasts a modern kitchen with microwave and dishwasher, a cosy fireplace, smart TV, laundry facilities, barbecue, parking, and air conditioning, perfect for exploring Oxford.
Miles Aweigh - Saint Michaels, MD
9.9 299 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.
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.
Bay House Retreat | Waterfront + Guest House - Saint Michaels, MD
No reviews

Bay House Retreat | Waterfront + Guest House

apartment, Stevensville
This private waterfront residence in Stevensville offers a secluded retreat with direct bay access and panoramic water views, perfect for those seeking coastal living.
This spacious four-bedroom, three-bathroom property accommodates up to ten guests and features a main home, a separate guest cottage, a garden, air conditioning, a Jacuzzi, and parking, with a screened-in porch ideal for enjoying the serene surroundings.
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