What are some interesting places to visit in or near Saint Michaels, MD?

Saint Michaels is a charming town with lots to see! You can visit the Chesapeake Bay Maritime Museum, explore the historic district with its quaint shops, or take a ferry to Tilghman Island for a taste of the local seafood scene. If you're feeling adventurous, you can also head to the Eastern Shore of Maryland for a day trip to explore the quaint towns and beautiful scenery.

What are the best Airbnb and vacation rentals in Saint Michaels, MD?

Stay In The Heart Of Saint Michaels , Waterfront Property - Kayaks - Private Dock - Near Town and Walk To Everything House are the most popular Airbnb and vacation rentals in Saint Michaels, MD among travelers.

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

The Saint Michaels waterfront is perfect for a leisurely stroll, and you can enjoy beautiful views of the harbor and the Chesapeake Bay. If you're looking for a longer bike ride, the scenic route along the Miles River is a great option. You can also check out the Eastern Shore Rail Trail for a longer, more challenging ride.

What are the most popular Airbnbs in Saint Michaels, MD?

Among the Airbnbs in Saint Michaels, MD, Walk To Everything House , Harrison House - In Town And On St Michaels Harbor and Small Historic House Downtown St Michaels are the most popular ones.

What sports or outdoor activites can visitors enjoy in and around Saint Michaels, MD?

Saint Michaels is a great place for water sports like kayaking, paddleboarding, and sailing. You can also go fishing in the Chesapeake Bay, or take a boat tour to see the local wildlife. If you're looking for something a little more active, you can go hiking or biking in the nearby forests and parks.

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

Waterfront Property - Kayaks - Private Dock - Near Town , St - Michaels Waterfront-pool/kayak/pier/firepit and Harrison House - In Town And On St Michaels Harbor are the best vacation rentals with a pool in Saint Michaels, MD.

What other towns or cities can be easily accessed from Saint Michaels, MD?

From Saint Michaels, you can easily drive to Annapolis, the capital of Maryland, which is about a 45-minute drive. You can also visit Easton, another historic town on the Eastern Shore, which is about a 30-minute drive from Saint Michaels.

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

The best rentals for families and kids in Saint Michaels, MD are Waterfront Property - Kayaks - Private Dock - Near Town , St - Michaels Waterfront-pool/kayak/pier/firepit and Harrison House - In Town And On St Michaels Harbor .

What amenities are commonly available in vacation rentals in Saint Michaels, MD?

Vacation rentals in Saint Michaels usually come with amenities like Wi-Fi, a fully equipped kitchen, laundry facilities, and sometimes even a private deck or patio. Many rentals also offer access to swimming pools, hot tubs, and other outdoor amenities.

What are the best rentals or Airbnbs with a jacuzzi in Saint Michaels, MD?

The best vacation rentals or Airbnb with a jacuzzi in Saint Michaels, MD are Blue Crab Lodge , Watch The Ever-changing Sunset Reflect Over The Eastern Bay and Suuri Rantahotelli - Josta On Henkeäsalpaavat Näkymät Auringonlaskuun .

What time of year is best to rent a vacation rental Saint Michaels, MD?

The best time to visit Saint Michaels is during the spring and fall, when the weather is mild and the crowds are smaller. You can also enjoy the town during the summer, but it can get quite hot and humid.

What are the local dishes in Saint Michaels, MD region?

The Eastern Shore is famous for its fresh seafood, so you'll find plenty of restaurants serving up crab cakes, oysters, and other Chesapeake Bay specialties. You can also try the local favorites like crab soup, fried chicken, and hushpuppies.

Saint Michaels, MD Vacation rentals & Airbnb

9.3 6 reviews

Crepe Myrtle | An Esvr Property

apartment, Tilghman Island

This Tilghman Island rental is conveniently located on the island, offering waterfront views and easy access to local restaurants and shops.
This 1470-square-foot, three-bedroom, two-bathroom house sleeps six, features a well-equipped kitchen with a dishwasher and microwave, and includes linens, towels, and a starter supply pack.

9.0 1 review

Captains Cove

house, Easton

Captains Cove, a five-bedroom Easton house rental, is located 12 miles from the Academy of the Arts in Saint Michaels and 62 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 2,730-square-foot property boasts a private pool, jacuzzi, and ample parking, comfortably accommodating up to 19 guests with five bathrooms and a fully equipped kitchen.

No reviews

Minutes From Downtown St. Michaels | Private Boat Ramp | Dock

apartment, Tilghman Island

This waterfront home on Tilghman Island offers stunning views and direct water access, conveniently located near Neavitt Park, Perry Cabin Park, and CL Open Field (all within 9 miles).
This 2,230-square-foot vacation rental boasts three bedrooms, three bathrooms, and sleeps six, featuring a fully equipped kitchen, in-house laundry, Wi-Fi, barbecue grills, and a spa.

10 1 review

Skipjack House | An Esvr Property

apartment, Tilghman Island

This McDaniel vacation home is a 3-bedroom, 2-bathroom apartment located a short drive from St. Michaels' historic harbor, Chesapeake Bay Maritime Museum, and shops.
This family-friendly rental accommodates up to six guests with two king bedrooms and one twin bedroom, featuring a private swimming pool, complimentary Wi-Fi, and two adult bikes and two children bikes for exploring the area.

9.8 331 reviews

Relax On Kent Island In 4 Bedroom Home W/waterview

apartment, Stevensville

This Stevensville vacation home is conveniently located just 5.5 miles from Matapeake State Park and within 12 miles of both Paul Reed Smith Guitars and Love Point State Park, offering easy access to the Chesapeake Bay and surrounding attractions. The house has earned excellent user, location, and cleanliness ratings, making it a top choice for your Stevensville getaway.
This 3-bedroom home comfortably accommodates up to 11 guests with its 1600 square feet of space. Enjoy a fully equipped kitchen, a relaxing garden, free Wi-Fi, and a smoke-free environment, making it perfect for family vacations or group getaways.

No reviews

Natures Rest On Grocelys Cove-waterfront With Pool

apartment, Easton

This Easton, Maryland waterfront rental is ideally situated between St. Michael's and Easton, offering easy access to both towns' attractions.
This four-bedroom, three-bathroom home features a private pool, kayak launch, sunroom, and accommodates up to eight guests, with amenities including a full kitchen, internet, and parking.

No reviews

Fairview Estate

house, Easton

Fairview Estate, located in Saint Michaels, Maryland, offers easy access to the Academy of the Arts (8.8 miles) and the Chesapeake Exploration Center (27 miles).
This 6,000-square-foot house boasts six bedrooms, six bathrooms, a private pool, and parking, comfortably accommodating up to 23 guests with amenities including a fully equipped kitchen and free Wi-Fi.

9.7 283 reviews

Perfect St. Michaels Getaway

apartment, Tilghman Island

Shipwright Cottage is located just eight miles from the charming town of St. Michaels, Maryland, offering a peaceful escape from the hustle and bustle of city life. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The two-bedroom cottage comfortably sleeps four guests and spans 1,190 square feet. Shipwright Cottage provides a fully equipped kitchen, a screened porch, a spa, and access to kayaks, bicycles, and a bike trailer, allowing guests to enjoy both indoor and outdoor activities.

10 10 reviews

Charming Waterfront Cottage Retreat Near St. Michaels

cottage, Tilghman Island

This waterfront cottage rental in Bozman, Maryland, offers easy access to St. Michaels' historic district, just minutes away and close to Neavitt and Perry Cabin Parks.
The 800-square-foot home features one bedroom, two bathrooms, sleeps two guests, and includes a gourmet kitchen, private dock, and panoramic Broad Creek views, perfect for kayaking, crabbing, and enjoying stunning sunsets.

9.2 16 reviews

Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

apartment, Oxford

This waterfront rental is located in Royal Oak, a quiet area just outside Oxford, Maryland, close to Easton and St. Michaels. It has received excellent user ratings, making it a popular choice for travelers. This 4-bedroom, 4-bathroom home offers 2830 square feet of space and comfortably accommodates up to 8 guests. The apartment features a fully equipped kitchen, a spacious living area, a private terrace, a jacuzzi, and a fitness center. Guests can enjoy the waterfront location, relax in the spa, or explore the surrounding area by kayak.

No reviews

Willows Dream

house, Oxford

Willows Dream, a 1,510-square-foot house in Oxford, is located 10 miles from the Academy of the Arts and 51 miles from Salisbury-Ocean City Wicomico Regional Airport.
This Oxford vacation rental sleeps 11 guests in three bedrooms, offering two bathrooms, a full kitchen, free Wi-Fi, and free private parking.

9.5 23 reviews

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

apartment, Tilghman Island

This waterfront home sits on a peaceful peninsula on Porters Creek, just minutes from the historic town of St. Michaels. It boasts excellent ratings for location, cleanliness, and overall experience, making it a top choice for travelers seeking a relaxing getaway.
The house features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy amenities like a private pool and spa, a well-equipped kitchen, a spacious open floor plan, and access to a variety of outdoor activities, including kayaking, crabbing, and waterfront views.

Best Saint Michaels, MD vacation rentals with a balcony

10 130 reviews

Kent Island Beach House - "Pink" House In Kentmorr

apartment, Stevensville

This Stevensville beach house is located just 9 miles from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to local attractions. The property has excellent ratings for user experience, location, and cleanliness.
This 1800 square foot vacation rental comfortably sleeps 14 guests in its four bedrooms. The house features a fully equipped kitchen, a fireplace, a jetted tub, a private terrace, a garden, a spa, a tennis court, and a playground, perfect for relaxing and entertaining.

10 2 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton

This 820 sq ft, 1-bedroom, 2-bathroom condo in downtown St. Michaels offers immediate access to the harbor, shops, and restaurants, providing prime waterfront proximity.
This accommodation sleeps 4 guests and features a fully stocked kitchen, gas fireplace, king bedroom with ensuite marble shower, two parking spaces, and high-speed WiFi, with family-friendly amenities available.

10 12 reviews

Saint Michaels Summer Retreat With Pool & Hot Tub

apartment, Tilghman Island

This waterfront apartment is located just a short distance from St. Michaels, offering easy access to the town's shops, dining, and attractions. The surrounding area is peaceful and offers a scenic escape from the hustle and bustle of city life.
The 3-bedroom home comfortably accommodates up to 6 guests. This apartment offers a private pool, a Jacuzzi, a terrace, a garden, and parking. Enjoy a relaxing vacation with all the comforts of home.

10 3 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville

This vacation home is situated in Stevensville, offering water views and an idyllic garden setting on Kent Island, 22 miles from Annapolis Harbor and 32 miles from Baltimore - Washington International Airport.
This spacious 1490 square foot house accommodates up to 21 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, complimentary private parking, free Wi-Fi, air conditioning, and an outdoor patio for relaxation.

Our Favorite Family-Friendly Vacation Rentals in Saint Michaels, MD

These family-friendly vacation rentals in Saint Michaels, MD offer spacious layouts and easy access to local beaches.

10 2 reviews

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Golf Cours

apartment, Easton

This Easton, Maryland waterfront vacation home boasts 6,000 square feet of space and is conveniently located within 9 miles of Bruffs Island, Pickering Creek Audubon Center, and the Historical Society of Talbot County.
This six-bedroom, six-bathroom residence offers a private pool, fitness center, tennis court, and accommodates up to 12 guests, complete with a fully equipped kitchen, laundry facilities, and barbecue grills.

10 4 reviews

Three Decks Overlook Marina Basin And Views Of The Chesapeake And Eastern Bays

apartment, Shady Side

This six-bedroom Stevensville apartment is located just a short walk from the beach and within walking distance of the marina, offering easy access to the waterfront and local attractions.
The 12-guest capacity apartment features multiple decks with picturesque views, a spacious entertainment room with a pool table, bar, and poker table, and is conveniently located near St. Michaels Winery, Annapolis Golf Club, Paul Reed Smith Guitars, and Phillips Wharf Environmental Center.

No reviews

Minutes From Downtown St. Michaels | Pool | Kayaks | 350 Ft Of Shoreline | Luxur

apartment, Tilghman Island

This waterfront farm is located in St. Michaels, Maryland, just a short drive from downtown St. Michaels and the Chesapeake Bay Maritime Museum. The area offers a peaceful escape with easy access to the region's history and attractions.
This spacious 6-bedroom, 6-bathroom home comfortably accommodates up to 12 guests. Enjoy a chef-inspired kitchen, a resort-style backyard with a swimming pool and a screened porch, perfect for relaxing and entertaining.

No reviews

The Weekender | An Esvr Property

apartment, Tilghman Island

This two-bedroom vacation farmhouse, located minutes from St. Michaels, offers easy access to shops and restaurants, and is a short drive from Tilghman Island.
The 2-bathroom rental features a bright, open-concept layout, sleeps four guests comfortably, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a garden, patio, and parking.

Frequently Asked Questions about vacation rentals in Saint Michaels, MD

What are some interesting places to visit in or near Saint Michaels, MD?
Saint Michaels is a charming town with lots to see! You can visit the Chesapeake Bay Maritime Museum, explore the historic district with its quaint shops, or take a ferry to Tilghman Island for a taste of the local seafood scene. If you're feeling adventurous, you can also head to the Eastern Shore of Maryland for a day trip to explore the quaint towns and beautiful scenery.
What are the best Airbnb and vacation rentals in Saint Michaels, MD?
Stay In The Heart Of Saint Michaels, Waterfront Property - Kayaks - Private Dock - Near Town and Walk To Everything House are the most popular Airbnb and vacation rentals in Saint Michaels, MD among travelers.
Which walking or cycling routes are the best in Saint Michaels, MD?
The Saint Michaels waterfront is perfect for a leisurely stroll, and you can enjoy beautiful views of the harbor and the Chesapeake Bay. If you're looking for a longer bike ride, the scenic route along the Miles River is a great option. You can also check out the Eastern Shore Rail Trail for a longer, more challenging ride.
What are the most popular Airbnbs in Saint Michaels, MD?
Among the Airbnbs in Saint Michaels, MD, Walk To Everything House, Harrison House - In Town And On St Michaels Harbor and Small Historic House Downtown St Michaels are the most popular ones.
What sports or outdoor activites can visitors enjoy in and around Saint Michaels, MD?
Saint Michaels is a great place for water sports like kayaking, paddleboarding, and sailing. You can also go fishing in the Chesapeake Bay, or take a boat tour to see the local wildlife. If you're looking for something a little more active, you can go hiking or biking in the nearby forests and parks.
What are the best vacation rentals with a pool in Saint Michaels, MD?
Waterfront Property - Kayaks - Private Dock - Near Town, St - Michaels Waterfront-pool/kayak/pier/firepit and Harrison House - In Town And On St Michaels Harbor are the best vacation rentals with a pool in Saint Michaels, MD.
What other towns or cities can be easily accessed from Saint Michaels, MD?
From Saint Michaels, you can easily drive to Annapolis, the capital of Maryland, which is about a 45-minute drive. You can also visit Easton, another historic town on the Eastern Shore, which is about a 30-minute drive from Saint Michaels.
What are the best rentals for families and kids in Saint Michaels, MD?
The best rentals for families and kids in Saint Michaels, MD are Waterfront Property - Kayaks - Private Dock - Near Town, St - Michaels Waterfront-pool/kayak/pier/firepit and Harrison House - In Town And On St Michaels Harbor.
What amenities are commonly available in vacation rentals in Saint Michaels, MD?
Vacation rentals in Saint Michaels usually come with amenities like Wi-Fi, a fully equipped kitchen, laundry facilities, and sometimes even a private deck or patio. Many rentals also offer access to swimming pools, hot tubs, and other outdoor amenities.
What are the best rentals or Airbnbs with a jacuzzi in Saint Michaels, MD?
The best vacation rentals or Airbnb with a jacuzzi in Saint Michaels, MD are Blue Crab Lodge, Watch The Ever-changing Sunset Reflect Over The Eastern Bay and Suuri Rantahotelli - Josta On Henkeäsalpaavat Näkymät Auringonlaskuun.
What time of year is best to rent a vacation rental Saint Michaels, MD?
The best time to visit Saint Michaels is during the spring and fall, when the weather is mild and the crowds are smaller. You can also enjoy the town during the summer, but it can get quite hot and humid.
What are the local dishes in Saint Michaels, MD region?
The Eastern Shore is famous for its fresh seafood, so you'll find plenty of restaurants serving up crab cakes, oysters, and other Chesapeake Bay specialties. You can also try the local favorites like crab soup, fried chicken, and hushpuppies.

Popular destinations

Best Saint Michaels, MD vacation rentals with parking

10 8 reviews

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

apartment, Tilghman Island

This private waterfront oasis, known as The Kipsy, is located on Porters Creek in Talbot County, offering direct access and creek views just minutes from St. Michaels.
This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a private pool, hot tub, fire pit, and dock, ideal for fishing or kayaking, with a fully equipped kitchen and spacious living areas designed for entertaining.

No reviews

The Farm At Cedar Cove | An Esvr Property

apartment, Oxford

This waterfront rental property in Royal Oak offers nearly 18 acres of private land with over 1,000 feet of waterfront access, located 15 miles from St. Michaels and 20 miles from Easton.
This 3-bedroom, 2-bathroom house accommodates up to 6 guests and features air conditioning, a full kitchen with a dishwasher and fridge, a screened-in porch, and an entertainment room with a 75-inch TV.

9.7 44 reviews

Cottage #6 Oar & Anchor Cottage

cottage, Tilghman Island

This charming cottage is located on Tilghman Island, a short walk from the Bay Hundred Community Pool and the Tilghman Island Pier, where you can enjoy fishing and crabbing. The cottage has received excellent ratings for its location, cleanliness, and user experience.
The cozy cabin has one bedroom and one bathroom, accommodating up to four guests. It offers a fully equipped kitchen, a dining table, a queen-size bed, and a futon that converts into a bed, as well as outdoor amenities like a fire pit, corn hole, and horseshoes.

9.6 4 reviews

Downtown Oxford | Outdoor Dining | Character Filled

apartment, Oxford

This Oxford, Mississippi duplex is located in a historic district, within walking distance of downtown Oxford and minutes from Play Ball Dog Park, Towne Park, and Towne Beach.
This three-bedroom, two-bathroom rental features a first-floor bedroom and bath, outdoor deck, screened porch, propane grill, two bikes, and accommodates up to six guests, with amenities including a fridge, microwave, and dishwasher.

Browse Vacation Rentals with a Pool in Saint Michaels, MD

Complement your time by the water with a dip in the pool at these Saint Michaels, MD vacation rentals with on-site swimming facilities.

No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

house, Trappe

This Trappe rental is located within the district, 5.6 miles from the Academy of the Arts and 48 miles from Salisbury-Ocean City Wicomico Regional Airport.
This four-bedroom house offers 2200 square feet of living space, accommodating up to 15 guests with amenities including a swimming pool, terrace, garden, and private parking.

10 1 review

Red Barn Farm | An Esvr Property

apartment, Tilghman Island

This five-bedroom, five-bathroom farmhouse is located in St. Michaels, Talbot County, Maryland, just a short drive from the attractions of Tilghman Island. The waterfront property features a chef-inspired kitchen, a swimming pool, and a spacious outdoor area perfect for gatherings, accommodating up to 12 guests.

9.8 30 reviews

Grandview - Cottage 1b, Queen Bed, Pool, Bay, Wifi

apartment, Tilghman Island

This charming duplex cottage on Tilghman Island is just a short distance from the harbor and the Chesapeake Bay, offering a peaceful escape in a picturesque setting. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage comfortably accommodates two guests and features a fully equipped kitchen, a screened porch, and access to waterfront amenities like a pool and boat house. You can enjoy the convenience of a fireplace, modern amenities, and the option of renting linens for a small fee.

No reviews

Bayside The Point

house, Oxford

This Royal Oak, Maryland home, located 8.5 miles from the Academy of the Arts and 59 miles from Baltimore/Washington International Thurgood Marshall Airport, offers a convenient base for exploring the region.
This 2,410-square-foot property boasts six bedrooms, four bathrooms, a private pool, hot tub, and parking, comfortably accommodating up to 23 guests.

Search Coastal Vacation Rentals near Saint Michaels, MD

Discover charming seaside vacation rentals in Saint Michaels, MD near the coast. Browse our favorite coastal picks to find your perfect beach-town match.

No reviews

Fairview Estate | An Esvr Property

apartment, Easton

No reviews

Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath

apartment, Stevensville

No reviews

Ships Ahoy

house, Oxford

9.7 60 reviews

Chesapeake Country Cottage: A Home Away From Home

apartment, Easton

Top-Rated 5-Star Vacation Rentals in Saint Michaels, MD

Refined interiors and prime locations make these luxury waterfront vacation rentals in Saint Michaels, MD the ideal choice for your stay.

10 4 reviews

Hawkeye Point | An Esvr Property

apartment, Tilghman Island

Best Vacation Rentals with a Steam Room in Saint Michaels, MD

Relax in style with an on-site sauna at these premium Saint Michaels, MD vacation rentals near the water.

No reviews

Downtown Oxford | Character Filled

apartment, Oxford

Vacation rentals in Saint Michaels, MD

Best Vacation rentals and Airbnb offers in Saint Michaels, MD

Crepe Myrtle | An Esvr Property

Captains Cove

Minutes From Downtown St. Michaels | Private Boat Ramp | Dock

Skipjack House | An Esvr Property

Relax On Kent Island In 4 Bedroom Home W/waterview

Natures Rest On Grocelys Cove-waterfront With Pool

Fairview Estate

Perfect St. Michaels Getaway

Charming Waterfront Cottage Retreat Near St. Michaels

Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

Willows Dream

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

Kent Island Beach House - "Pink" House In Kentmorr

Downtown Flat Walk To Dining & Shops Sleeps 4

Saint Michaels Summer Retreat With Pool & Hot Tub

Relax On Kent Island In 3 Bedroom Home W/waterview

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Golf Cours

Three Decks Overlook Marina Basin And Views Of The Chesapeake And Eastern Bays

Minutes From Downtown St. Michaels | Pool | Kayaks | 350 Ft Of Shoreline | Luxur

The Weekender | An Esvr Property

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

The Farm At Cedar Cove | An Esvr Property

Cottage #6 Oar & Anchor Cottage

Downtown Oxford | Outdoor Dining | Character Filled

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

Red Barn Farm | An Esvr Property

Grandview - Cottage 1b, Queen Bed, Pool, Bay, Wifi

Bayside The Point

Fairview Estate | An Esvr Property

Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath

Ships Ahoy

Chesapeake Country Cottage: A Home Away From Home

Hawkeye Point | An Esvr Property

Downtown Oxford | Character Filled