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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

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.
Bayside The Point | An Esvr Property - Saint Michaels, MD
No reviews

Bayside The Point | An Esvr Property

apartment, Oxford
This charming waterfront cottage is located on the Chesapeake Bay, just 20 kilometres from the historic town of St. Michaels and 30 kilometres from Easton, offering a peaceful retreat near the water. The cottage provides comfortable accommodation for 12 guests, with 6 bedrooms and 4 bathrooms, as well as a separate garage apartment with its own kitchen. Guests can enjoy a range of amenities including a swimming pool, a fully equipped kitchen, and a private outdoor area, perfect for relaxing and enjoying the beautiful scenery.
Sm's Premier Rental Heated Pool (Opens 4/3) - Saint Michaels, MD
10 265 reviews

Sm's Premier Rental Heated Pool (Opens 4/3)

apartment, Easton
Harbor Hideaway is a charming cottage located in downtown Saint Michaels, Maryland, just a short walk from the waterfront and a few minutes from the town's attractions. The cottage has consistently received excellent ratings for location, cleanliness, and overall experience.
The cottage spans 111 square meters and comfortably accommodates up to four guests. It features a fully equipped kitchen, a private swimming pool, a terrace, a garden, a spa, a tennis court, and parking, making it perfect for a relaxing and enjoyable stay.
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.

Best family friendly Saint Michaels, MD lodging

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

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife - Saint Michaels, MD
9.8 53 reviews

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife

apartment, Easton
This newly renovated cottage is located in the heart of historic St. Michaels, just a short walk from its charming restaurants, boutiques, and waterfront. The property has received excellent reviews from previous guests.
The three-bedroom, three-bathroom home is 119 square metres in size. Amenities include a fully equipped kitchen, air conditioning, a garden, a spa, parking, and internet access.
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.
Bayou On The Bay - Saint Michaels, MD
No reviews

Bayou On The Bay

apartment, Stevensville
This bayfront flat in Stevensville offers exceptional water views and is situated conveniently near upscale dining, the Naval Academy, and waterfront attractions.
This 130 square metre apartment accommodates up to six guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, and a private jacuzzi, with opportunities for jet skiing, kayaking, and cycling nearby.
The Little Anchor Cottage, St. Michaels, Md - Saint Michaels, MD
9.9 294 reviews

The Little Anchor Cottage, St. Michaels, Md

apartment, Easton
The Little Anchor cottage is located in the Historic District of St. Michaels, Maryland, just one block from downtown shops and restaurants and a 5 to 15 minute walk from waterfront dining, the Chesapeake Bay Maritime Museum, Muskrat Park, and Hollis Park. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The charming two-bedroom property can accommodate up to four guests and features a fully equipped kitchen, a spacious screened porch, a garden, and high-speed Wi-Fi. Guests can enjoy dedicated workspaces, air conditioning, and the convenience of being pet-friendly and family-friendly.

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

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.
Downtown St. Michaels Studio  Walk To Waterfront, Dining & Shops - Saint Michaels, MD
10 38 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.
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.
Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 4 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville
This Stevensville holiday home on Kent Island offers a tranquil waterside retreat, situated 35 kilometres from Annapolis Harbour and 51 kilometres from Baltimore-Washington International Airport.
This spacious 138 square metre property accommodates up to 21 guests with four bedrooms, three bathrooms, a fully equipped kitchen, a living room, and outdoor space including a garden and patio, complemented by free private parking and WiFi.

Best Saint Michaels, MD accommodations with a kitchen

St. Michaels Stay | Walking Distance To Downtown - Saint Michaels, MD
9.7 18 reviews

St. Michaels Stay | Walking Distance To Downtown

apartment, Easton
This St. Michaels apartment, in Easton, Maryland, offers easy walking and cycling access to the town centre, eliminating the need for a car.
The three-bedroom property sleeps six, includes a fully equipped kitchen with fridge, microwave, and dishwasher, and boasts keyless entry, air conditioning, parking, and pet-friendly options for a £160 fee.
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.
The Suite At Mostly Porches - Saint Michaels, MD
10 81 reviews

The Suite At Mostly Porches

house, Easton
This Saint Michaels suite, a short walk from the Chesapeake Bay Maritime Museum and the St. Michaels Museum, offers stunning harbour views and proximity to Lyons Distilling Company within the Old Mill complex.
The 45-square-metre apartment includes a king-size bed, sofa, and a kitchenette with a fridge, freezer, microwave, and coffee makers, accommodating two guests and featuring a private bathroom and off-street parking.
St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly - Saint Michaels, MD
9.8 43 reviews

St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly

apartment, Tilghman Island
This spacious holiday home is located in Sherwood, Talbot County, Maryland, a tranquil rural area on the waterfront, just 5 kilometres from Tilghman Island and a 20-minute drive from the centre of St. Michaels. It has received excellent user ratings for its comfortable accommodation and extensive amenities.
The property has 5 bedrooms, 7 bathrooms, 2 full kitchens, 2 living rooms, and 2 dining rooms, covering 418 square metres and accommodating up to 10 guests. This large home offers a private pool and spa area, a garden, a sauna, a Jacuzzi, a wrap-around porch with stunning views, and direct access to the water with a private dock, making it perfect for families and groups seeking a relaxing and enjoyable getaway.
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