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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

Brand-new Pool! Waterfront Bozman Village Home - Saint Michaels, MD
10 5 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.
St. Michaels Waterfront Home With Pool - Saint Michaels, MD
10 2 reviews

St. Michaels Waterfront Home With Pool

apartment, Tilghman Island
This newly built waterfront holiday home on Maryland's Eastern Shore offers a peaceful escape just a few minutes' drive from the attractions and dining of St. Michaels in Talbot County.
This four-bedroom, four-bathroom property accommodates up to eight guests and features a private swimming pool, air conditioning, a full kitchen, and internet access, with parking and a garden also provided.
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.
Hawkeye Point | An Esvr Property - Saint Michaels, MD
10 5 reviews

Hawkeye Point | An Esvr Property

apartment, Tilghman Island
This three-bedroom, two-bathroom Eastern Shore cedar Lindal home, near St Michael's, Maryland, offers breathtaking Broad Creek views and is a short drive from the historic town.
The 3-bedroom property sleeps six, features a chef-inspired kitchen, dishwasher, air conditioning, a swimming pool, garden, and screened patio; linens and towels are provided.

Best family friendly Saint Michaels, MD lodging

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

Thorneton Point Estate - Saint Michaels, MD
9.6 24 reviews

Thorneton Point Estate

apartment, Oxford
This luxurious six-bedroom property, sleeping up to twelve guests, is situated near St. Michaels, Maryland, approximately 10 kilometres from St. Michaels Village, St. Michaels Winery, and the Classic Motor Museum – note that this property is not located in Oxford as initially stated.
The self-catering residence boasts a private pool, hot tub, fitness centre, and barbecue facilities, alongside a fully equipped kitchen, five bathrooms, and a balcony, making it ideal for large family groups or parties.
The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground! - Saint Michaels, MD
9.6 5 reviews

The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground!

apartment, Stevensville
This waterfront accommodation in Stevensville, situated on Chews Creek which flows into the Chesapeake Bay, is a 10-minute walk from Matapeake Beach and a short drive from the Chesapeake Bay Bridge and Kent Narrows.
This spacious 279 square meter dwelling accommodates up to 12 guests across 5 bedrooms and 4 bathrooms, boasting amenities such as a private pool open April to October, a sand firepit, panoramic water views, a dedicated "car bar," a vintage record player, and a TV-free "Unplug Zone" for games and conversation.
Mill Point | An Esvr Property - Saint Michaels, MD
10 5 reviews

Mill Point | An Esvr Property

apartment, Tilghman Island
This five-bedroom waterfront property, situated in Talbot County, Maryland, overlooks Harris Creek and offers stunning views of Tilghman Island.
This fully renovated house boasts a spacious great room with 12' x 8' bifold doors, a fully equipped kitchen, four bathrooms, and accommodates up to ten guests, featuring a swimming pool and direct waterfront access to the Chesapeake Bay.
St. Michaels Waterfront-pool/kayak/pier/firepit - Saint Michaels, MD
10 192 reviews

St. Michaels Waterfront-pool/kayak/pier/firepit

house, Easton
This charming house is located in Talbot County, Maryland, just a short drive from the historic towns of Easton and St Michaels, offering a peaceful retreat in a beautiful setting. The property enjoys excellent ratings for location, cleanliness and user experience.
The house is spacious, with 5 bedrooms and a floor area of 297 square metres, comfortably accommodating up to 10 guests. It offers a range of amenities, including a private pool, a garden, a spa, and a fully equipped kitchen, as well as kayaks, bikes, and a boat slip for enjoying the surrounding area.

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

Crabbers Cove - Saint Michaels, MD
8.0 1 review

Crabbers Cove

house, Easton
Crabbers Cove, a spacious house in Saint Michaels, Maryland, is situated 19 kilometres from the Academy of the Arts and 100 kilometres from Baltimore-Washington International Airport.
This three-bedroom, three-bathroom property offers 196 square metres of living space, sleeping up to 11 guests and including free Wi-Fi, private parking, and a fully equipped kitchen; nearby activities include boating and fishing on the Chesapeake Bay.
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.
25 Bedrooms - Retreat Center Waterfront Renovated - Saint Michaels, MD
No reviews

25 Bedrooms - Retreat Center Waterfront Renovated

house, Oxford
This luxurious 25-bedroom property, ideal for large groups, is situated in Royal Oak, Maryland, approximately 21 kilometres from the Academy of the Arts and 105 kilometres from Salisbury-Ocean City Wicomico Regional Airport; note that this property is not located in Oxford.
Boasting a 950 square metre floor area, this waterfront residence offers a swimming pool, fitness centre, and ample parking, accommodating up to 79 guests with 20 bathrooms and a fully equipped kitchen.

Best Saint Michaels, MD accommodations with a kitchen

Minutes From Downtown St. Michaels | Character Filled - Saint Michaels, MD
8.0 2 reviews

Minutes From Downtown St. Michaels | Character Filled

apartment, Tilghman Island
This two-bedroom holiday home in Bozman, a five-minute (8 km) drive from St. Michaels, offers easy access to the town's waterfront restaurants and shops.
The property features a spacious open-plan layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, patio, yard games, and bikes, plus air conditioning and Wi-Fi.
Miles Rest - Saint Michaels, MD
No reviews

Miles Rest

house, Easton
Miles Rest, a house in Royal Oak, Maryland, is situated 11 kilometres from the Academy of the Arts and 48 kilometres from the Chesapeake Exploration Centre.
This Easton property boasts 279 square metres of floor space, offering five bedrooms, four bathrooms, a private pool, jacuzzi, free Wi-Fi and parking, accommodating up to 19 guests.
Newly Renovated Modern Waterfront Home - Saint Michaels, MD
10 40 reviews

Newly Renovated Modern Waterfront Home

apartment, Easton
This newly renovated riverside mansion is situated in Easton, just a short distance from the town centre and offering stunning views across the water. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The home has five bedrooms and five bathrooms, comfortably accommodating up to 15 guests. Enjoy a range of amenities including a swimming pool, fitness centre, and a spacious garden, perfect for relaxing or entertaining.
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