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

Blue Herons Villa - Saint Michaels, MD
No reviews

Blue Herons Villa

house, Oxford
Blue Herons Villa, a spacious house in Royal Oak, Maryland, is located 14 kilometres from the Academy of the Arts and 95 kilometres from Baltimore–Washington International Thurgood Marshall Airport.
This five-bedroom property boasts 255 square metres of floor space, accommodating up to 19 guests, and includes a private swimming pool, fully equipped kitchen, free Wi-Fi, and free parking; it is unsuitable for bachelor/bachelorette parties.
Two Oysters House 
2025 Remodel - Saint Michaels, MD
9.5 153 reviews

Two Oysters House 2025 Remodel

apartment, Tilghman Island
This four-bedroom apartment is located in a peaceful rural retreat in St. Michaels, Maryland, just 4km from the centre of town, including the Inn at Perry Cabin and Museum, which is easily accessible by bike. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers over 220 square metres of living space, comfortably accommodating up to eight guests. Enjoy access to a private saltwater pool, dock, hot tub, bikes, kayaks, and a fully equipped kitchen, providing everything you need for a relaxing and enjoyable stay.
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.
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.

Best family friendly Saint Michaels, MD lodging

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

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.
Blue Heron's Villa | An Esvr Property - Saint Michaels, MD
10 2 reviews

Blue Heron's Villa | An Esvr Property

apartment, Oxford
This luxurious five-bedroom house, situated in Talbot County on Edge Creek, offers a tranquil waterfront escape approximately 80km from Oxford city centre.
The property boasts a spacious layout including an open-plan kitchen, dining area, formal living room with fireplace, private in-ground pool (open May 22nd - October 15th), private dock, and sleeps up to ten guests, with all modern amenities.
Captain's Cove | An Esvr Property - Saint Michaels, MD
10 10 reviews

Captain's Cove | An Esvr Property

apartment, Easton
This waterfront holiday home is situated in St. Michaels, just 3 kilometres from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it an ideal base for exploring this charming town. The property has received excellent ratings for its location, cleanliness, and overall experience.
The five-bedroom property spans 254 square metres and comfortably accommodates up to 10 guests. This spacious house offers a range of amenities including a private pool, a hot tub, a spa, a fitness centre, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
True St. Michaels 6 Acre Waterfront W/heated Pool - Saint Michaels, MD
10 197 reviews

True St. Michaels 6 Acre Waterfront W/heated Pool

cabin, Easton
The Spencer Creek Cabin is situated just outside of Historic Downtown Saint Michaels, a 5-10 minute bike ride away, with a grocery store, petrol station and coffee shop across the street. The cabin has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The property has five bedrooms, three bathrooms and a floor area of 279 square metres, comfortably accommodating up to eight guests. Amenities include a private swimming pool, a hot tub, a tennis court, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.

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 watersports, with plenty of opportunities for sailing, kayaking, and fishing. If you're looking for something a bit more relaxed, you can always take a walk or bike ride along the scenic waterfront. There's also a beautiful state park just a short drive away, with hiking trails and a beach.
  • 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.

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

    Spring and autumn are the best times to visit Saint Michaels, the weather is mild and the crowds are smaller. Summer can be hot and humid, but it's a great time to enjoy the beaches and watersports. Winter can be chilly, but there's still plenty to see and do, especially if you enjoy the quieter side of things.
  • 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.

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

    Easton is a charming town about a 20-minute drive away, with a thriving arts scene and plenty of shops and restaurants. Annapolis, the capital of Maryland, is about an hour's drive away and is a great place to explore history and culture. And of course, you can always take a day trip to Baltimore or Washington D.C., both of which are within a two-hour drive.
  • What are the best accommodations with a jacuzzi in Saint Michaels, MD?

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

    There are a variety of accommodations in Saint Michaels, from charming bed and breakfasts to luxury hotels. Most accommodations offer amenities such as free Wi-Fi, parking, and breakfast. Some also have pools, fitness centers, and restaurants.
  • What are the best accommodations for families and kids in Saint Michaels, MD?

  • 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 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

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.
Saint Michaels Summer Retreat With Pool & Hot Tub - Saint Michaels, MD
10 12 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.
The Suite At Mostly Porches - Saint Michaels, MD
10 84 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.
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.

Best Saint Michaels, MD accommodations with a kitchen

Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien - Saint Michaels, MD
9.8 6 reviews

Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien

apartment, Oxford
This luxurious five-bedroom waterfront property near Oxford is situated approximately 3km from the Oxford Museum and 4km from Play Ball Dog Park, offering scenic views and easy access to St Michael's Village and St Michael's Winery within a 14.5km radius.
Boasting 331 square metres of floor space, this self-catering house sleeps eight guests and includes four bathrooms, a complete kitchen with dishwasher, a terrace, garden, spa, parking, and free Wi-Fi.
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.
The Farm At Cedar Cove | An Esvr Property - Saint Michaels, MD
No reviews

The Farm At Cedar Cove | An Esvr Property

apartment, Oxford
This waterfront property in Royal Oak offers 18 acres of secluded farmland with over 1,000 feet of private shoreline, situated 15 minutes from St. Michaels and Easton.
This renovated 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, garden, parking, and internet, with the Oxford-Bellevue Ferry and cycling routes nearby.
Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Kayaks | Privat - Saint Michaels, MD
10 15 reviews

Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Kayaks | Privat

apartment, Easton
This Easton, Maryland waterfront property, situated 14.5km from the Historical Society of Talbot County, Easton Cycle and Sport, and the Avalon Theatre, offers stunning water views and direct water access.
This 302 square metre house boasts five bedrooms, four bathrooms, sleeps ten guests, and includes a private pool, jacuzzi, tennis court, and a fully equipped kitchen; free Wi-Fi is also provided.
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