What is Saint Michaels, MD best known for?

Saint Michaels is best known for its charming waterfront setting and its maritime history. The town is home to the Chesapeake Bay Maritime Museum, which has a collection of historic boats and exhibits. Saint Michaels is also a popular destination for sailing, kayaking, and paddleboarding.

What are the best apartments in Saint Michaels, MD?

Among the apartments in Saint Michaels, MD, Stay In The Heart Of Saint Michaels , Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More and Waterfront Property - Kayaks - Private Dock - Near Town are the most popular ones.

What are the closest cities to visit near Saint Michaels, MD?

The closest major city to Saint Michaels is Easton, which is about 15 minutes away. You can also visit Annapolis, the state capital of Maryland, which is about 45 minutes away. For a taste of the big city, you can take a day trip to Baltimore, which is about 1 hour and 30 minutes away.

What are the best apartments with a pool in Saint Michaels, MD?

Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More , Waterfront Property - Kayaks - Private Dock - Near Town and Baydream Believer - Eastern Shore Md Luxury Waterfront Home are the best apartments with a pool in Saint Michaels, MD.

What are the best ways to relax in Saint Michaels, MD?

Saint Michaels is a great place to relax and unwind. You can take a leisurely stroll along the waterfront, enjoy a picnic in the park, or simply sit back and enjoy the view. There are also a number of spas and salons in the town where you can pamper yourself.

What are the best apartments with a jacuzzi in Saint Michaels, MD?

The best apartments with a jacuzzi in Saint Michaels, MD are Beautiful Waterfront Home W\/ Pool In St - Michaels , Blue Crab Lodge and Watch The Ever-changing Sunset Reflect Over The Eastern Bay .

What are the advantages of choosing an apartment for your stay in Saint Michaels, MD?

Apartments offer more space and privacy than hotels, and they can be a great option for families or groups of friends. You can also often find apartments with kitchens, which can be a big advantage if you're planning on cooking some of your own meals.

What are the best apartments for families and kids in Saint Michaels, MD?

The best apartments for families and kids in Saint Michaels, MD are Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More , Waterfront Property - Kayaks - Private Dock - Near Town and True In-town St Michaels 6 Acre Waterfront - Heated Pool .

What are the best pet friendly apartments in Saint Michaels, MD?

The best pet friendly apartments in Saint Michaels, MD are Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More , Waterfront Property - Kayaks - Private Dock - Near Town and Luxurious And Extremely Private Waterfront Estate (Sorry - No Weddings) .

What are the best apartments with parking in Saint Michaels, MD?

Stay In The Heart Of Saint Michaels , Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More and Waterfront Property - Kayaks - Private Dock - Near Town are the best apartments with parking in Saint Michaels, MD.

Saint Michaels, MD Holiday Apartments and Self Catering

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.

9.9 35 reviews

Lovely Waterfront Cottage On 2 Acres, St. Michaels

apartment, Easton

This Easton holiday home is situated near St. Michaels, Maryland, within a short walk or cycle ride (approximately 1.6 km) of its shops and restaurants.
Sleeping six, this three-bedroom, two-bathroom property boasts a kitchen with dishwasher, air conditioning, a garden, and Wi-Fi; a private dock offering 2.1 metres of water depth is also available for boating enthusiasts.

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.

9.5 152 reviews

Two Oysters House 2025 Remodel Waterfront W/ Pool In St. Michaels

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.

9.7 163 reviews

The Farm House At Hunting Creek - Pets $50 A Night

apartment, Easton

This gated estate carriage house is located in a rural setting just 10km from Easton's shops, restaurants, and bars, and 15km from the historic town of St. Michaels. The property enjoys excellent user, location and cleanliness ratings.
The spacious house has five bedrooms, sleeping up to 10 guests, and comes with a fully equipped kitchen, satellite TV, Wi-Fi and air conditioning. Guests can enjoy the peace and quiet of the 80-acre estate, with access to a pathway leading to the waterfront for scenic views and potential fishing or kayaking.

9.5 4 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton

This flat is located in the centre of St. Michaels, Maryland, within walking distance of St. Michaels' dining, shopping, and waterfront attractions.
This one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, a gas fireplace, a king-sized bed, a marble walk-in shower, and two dedicated parking spaces, with high-speed WiFi and an in-unit washer and dryer also provided.

10 3 reviews

Ferry View | An Esvr Property

apartment, Oxford

This four-bedroom apartment is situated in Talbot County, just a short distance from Oxford's charming town centre and the Chesapeake Bay, offering a peaceful setting away from the bustle of city life. The apartment has received excellent ratings for its location, cleanliness and overall experience.
The spacious property comfortably accommodates up to eight guests, with multiple bedrooms and entertainment areas. This well-equipped home includes a fully fitted kitchen, air conditioning, a garden, parking, and internet access, as well as a courtesy starter pack with essential items.

9.6 44 reviews

Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

apartment, Easton

This charming apartment is located in St. Michaels, just a short drive from the Bay Hundred Community Pool, golf courses, and the town centre. It has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment is spacious, covering 196 square metres and comfortably accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. You can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as access to the internet.

9.8 164 reviews

Walk To Everything House

apartment, Easton

This charming house is located in St. Michaels, a short 1-kilometre walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and can accommodate up to six guests. It includes a fully equipped kitchen, a garden, a spa, and parking, providing everything you need for a comfortable and enjoyable stay.

Search Apartments by the Shore Saint Michaels, MD

Base your coastal break at comfortable shoreside holiday apartments located a short trip from beaches in Saint Michaels, MD.

10 2 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton

This St. Michaels flat is located in the downtown district, a short walk from the waterfront, dining, and shopping areas.
This 76 square meter flat accommodates up to 4 guests, featuring 1 bedroom, 2 bathrooms, a fully stocked kitchen with a coffee bar, a gas fireplace, a king-sized bedroom with a Smart TV, a spa-like ensuite bathroom, high-speed WiFi, an in-unit washer and dryer, and designated parking for two vehicles.

Find the Best Family-Friendly Self-Catering Apartments in Saint Michaels, MD

Kid-friendly holiday apartments in Saint Michaels, MD offer close proximity to lifeguarded beaches and plenty of room for the whole family to spread out.

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.

9.9 297 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.

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.

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.

Frequently asked questions about apartment rentals in Saint Michaels, MD

What is Saint Michaels, MD best known for?
Saint Michaels is best known for its charming waterfront setting and its maritime history. The town is home to the Chesapeake Bay Maritime Museum, which has a collection of historic boats and exhibits. Saint Michaels is also a popular destination for sailing, kayaking, and paddleboarding.
What are the best apartments in Saint Michaels, MD?
Among the apartments in Saint Michaels, MD, Stay In The Heart Of Saint Michaels, Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More and Waterfront Property - Kayaks - Private Dock - Near Town are the most popular ones.
What are the closest cities to visit near Saint Michaels, MD?
The closest major city to Saint Michaels is Easton, which is about 15 minutes away. You can also visit Annapolis, the state capital of Maryland, which is about 45 minutes away. For a taste of the big city, you can take a day trip to Baltimore, which is about 1 hour and 30 minutes away.
What are the best apartments with a pool in Saint Michaels, MD?
Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More, Waterfront Property - Kayaks - Private Dock - Near Town and Baydream Believer - Eastern Shore Md Luxury Waterfront Home are the best apartments with a pool in Saint Michaels, MD.
What are the best ways to relax in Saint Michaels, MD?
Saint Michaels is a great place to relax and unwind. You can take a leisurely stroll along the waterfront, enjoy a picnic in the park, or simply sit back and enjoy the view. There are also a number of spas and salons in the town where you can pamper yourself.
What are the best apartments with a jacuzzi in Saint Michaels, MD?
The best apartments with a jacuzzi in Saint Michaels, MD are Beautiful Waterfront Home W\/ Pool In St - Michaels, Blue Crab Lodge and Watch The Ever-changing Sunset Reflect Over The Eastern Bay.
What are the advantages of choosing an apartment for your stay in Saint Michaels, MD?
Apartments offer more space and privacy than hotels, and they can be a great option for families or groups of friends. You can also often find apartments with kitchens, which can be a big advantage if you're planning on cooking some of your own meals.
What are the best apartments for families and kids in Saint Michaels, MD?
The best apartments for families and kids in Saint Michaels, MD are Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More, Waterfront Property - Kayaks - Private Dock - Near Town and True In-town St Michaels 6 Acre Waterfront - Heated Pool.
What are the best pet friendly apartments in Saint Michaels, MD?
The best pet friendly apartments in Saint Michaels, MD are Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More, Waterfront Property - Kayaks - Private Dock - Near Town and Luxurious And Extremely Private Waterfront Estate (Sorry - No Weddings).
What are the best apartments with parking in Saint Michaels, MD?
Stay In The Heart Of Saint Michaels, Modern St - Michaels Estate -Pier - Pool - Gas Fire Pit - Bikes - Kayaks & More and Waterfront Property - Kayaks - Private Dock - Near Town are the best apartments with parking in Saint Michaels, MD.

Popular destinations

Guest-Favourite Pet-Friendly Holiday Apartments in Saint Michaels, MD

Enjoy stress-free seaside trips from a dog-friendly holiday apartment in Saint Michaels, MD near local beaches.

No reviews

Downtown Oxford | Character Filled

apartment, Oxford

This Oxford apartment, a 14-minute walk from the Oxford Museum and a 24-kilometre drive from the Talbot County Visitor Centre, offers convenient access to local attractions.
The three-bedroom, two-bathroom property boasts a fully equipped kitchen, including a dishwasher, in-unit laundry facilities, air conditioning, free Wi-Fi, and parking, comfortably accommodating families or groups of up to six.

9.6 124 reviews

Dollhouse In Central Historic St Michaels

apartment, Easton

This charming house is located in St. Michaels, a picturesque town on Maryland's Eastern Shore, just 1 kilometre from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms, accommodating up to four guests, and features a fully equipped kitchen, two bathrooms, a washing machine, and a Smart TV. Guests can enjoy a spa tub, garden, barbecue grills, and a terrace, making it ideal for relaxation and outdoor dining.

9.8 156 reviews

Waterfront Property, Kayaks, Private Dock, Near Town

apartment, Easton

This waterfront holiday home is located just three miles from St. Michaels Winery and Museum, offering easy access to local attractions and a peaceful setting. The property has received excellent guest ratings, indicating a high standard of comfort and service.
The home features three bedrooms and three bathrooms, providing ample space for up to six guests. A range of amenities are available, including a swimming pool, spa, garden, and barbecue facilities, ensuring a relaxing and enjoyable stay.

10 1 review

The Weekender | An Esvr Property

apartment, Tilghman Island

This two-bedroom farmhouse, situated minutes from St. Michaels town centre, offers easy access to its shops and restaurants, lying approximately a few kilometres from Tilghman Island.
The property provides 4 guests with a fully equipped kitchen, including a fridge, microwave, and dishwasher, two bathrooms and a tranquil patio overlooking manicured gardens; linens and towels are included.

Best Holiday Apartments with a Pool in Saint Michaels, MD

A holiday apartment with a swimming pool in Saint Michaels, MD is a brilliant base for a refreshing dip to complement a day by the water.

10 3 reviews

Waterfront | Pet Friendly & Close To St. Michaels

apartment, Tilghman Island

This four-bedroom, three-bathroom waterfront property is located in Bozman, Maryland, a short drive (approximately 8 km) from St. Michaels and its Chesapeake Bay Maritime Museum.
This self-catering holiday home sleeps eight guests and boasts a private swimming pool, private dock for crabbing and kayaking, and two distinct living areas, plus a fully equipped kitchen and complimentary kayaks.

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.

9.6 27 reviews

Waterfront Estate - Riverslie On The Miles River

apartment, 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.

Best Saint Michaels, MD holiday apartments with air conditioning

9.6 4 reviews

Downtown Oxford | Outdoor Dining | Character Filled

apartment, Oxford

10 15 reviews

St. Michaels Waterfront Home With Private Dock

apartment, Easton

10 2 reviews

Skipjack House | An Esvr Property

apartment, Tilghman Island

Popular Luxury Holiday Apartments in Saint Michaels, MD

High standards of comfort, quality, and a prime location define these luxury holiday apartments in Saint Michaels, MD, ensuring a premium stay.

9.6 4 reviews

Charming 3 Bedroom Cottage 6 Miles To St. Michaels

apartment, Tilghman Island

Choose the Right Self-Catering Apartments with Free Parking in Saint Michaels, MD

Each holiday apartment here includes a car park, making the coast and local beaches easy to access from the moment you arrive.

9.9 92 reviews

Private+cozy-3br+2ba-1mile To Historic Downtown Saint Michaels

apartment, Tilghman Island

10 15 reviews

Cozy, Family-friendly Log Cabin-st. Michaels

apartment, Oxford

9.6 18 reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

apartment, Trappe

9.9 22 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton

Top-Rated Holiday Apartments with a Hot Tub in Saint Michaels, MD

Whether you prefer a jacuzzi or a hot tub, every holiday apartment near the water in Saint Michaels, MD includes one for a private soak by the sea.

9.5 23 reviews

St. Michaels Escape | Pool, Hot Tub & Fire Pit

apartment, Tilghman Island

10 5 reviews

Brand-new Pool! Waterfront Bozman Village Home

apartment, Tilghman Island

10 9 reviews

St. Michaels Escape | Pool, Hot Tub & Fire Pit

apartment, Tilghman Island

9.0 6 reviews

Minutes From Downtown St. Michaels | Guest House | Pool | Private Dock

apartment, Oxford

Compare Holiday Apartments with a Balcony in Saint Michaels, MD

Private balconies with views of the water and coastal scenery come as standard at these holiday apartments near the water in Saint Michaels, MD.

No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Easton

10 1 review

Charming 3-bedroom In Village Of Claiborne Book 3 Nights Get 4th Free Strn26-6

apartment, Claiborne

Best apartment offers in Saint Michaels, MD

45 Best apartments in Saint Michaels, MD

Bayou On The Bay

Lovely Waterfront Cottage On 2 Acres, St. Michaels

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

Two Oysters House 2025 Remodel Waterfront W/ Pool In St. Michaels

The Farm House At Hunting Creek - Pets $50 A Night

Downtown Flat Walk To Dining & Shops Sleeps 4

Ferry View | An Esvr Property

Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Walk To Everything House

Downtown Flat Walk To Dining & Shops Sleeps 4

Thorneton Point Estate

The Little Anchor Cottage, St. Michaels, Md

Minutes From Downtown Easton And St. Michaels | Pool

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

Downtown Oxford | Character Filled

Dollhouse In Central Historic St Michaels

Waterfront Property, Kayaks, Private Dock, Near Town

The Weekender | An Esvr Property

Waterfront | Pet Friendly & Close To St. Michaels

Saint Michaels Summer Retreat With Pool & Hot Tub

Waterfront Estate - Riverslie On The Miles River

Downtown Oxford | Outdoor Dining | Character Filled

St. Michaels Waterfront Home With Private Dock

Skipjack House | An Esvr Property

Charming 3 Bedroom Cottage 6 Miles To St. Michaels

Private+cozy-3br+2ba-1mile To Historic Downtown Saint Michaels

Cozy, Family-friendly Log Cabin-st. Michaels

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

Downtown St. Michaels | Porch + Pet-friendly

St. Michaels Escape | Pool, Hot Tub & Fire Pit

Brand-new Pool! Waterfront Bozman Village Home

St. Michaels Escape | Pool, Hot Tub & Fire Pit

Minutes From Downtown St. Michaels | Guest House | Pool | Private Dock

Apartment ∙ 1 Bedroom ∙ 4 Guests

Charming 3-bedroom In Village Of Claiborne Book 3 Nights Get 4th Free Strn26-6