What are the must-see sites in or near Saint Michaels, MD?

You have to check out the Chesapeake Bay Maritime Museum, it's a great way to learn about the history of the area. The Saint Michaels Museum is also a must-see, with exhibits on the town's past. And of course, you can't miss the beautiful waterfront, with its charming shops and restaurants.

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.

How can travelers reach Saint Michaels, MD?

The easiest way to get to Saint Michaels is to drive, it's about a 90-minute drive from Baltimore and a 2-hour drive from Washington, D.C. You can also take the train to Easton and then a taxi or bus to Saint Michaels. If you're coming from further away, you can fly into Baltimore-Washington International Airport (BWI) and then rent a car.

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 outdoor activities can visitors enjoy in and around Saint Michaels, MD?

There are plenty of outdoor activities to enjoy in Saint Michaels. You can go kayaking or canoeing on the Miles River, or take a boat tour to see the local wildlife. There's also a great walking trail along the waterfront, and you can rent bikes and explore the town and surrounding countryside.

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

The best accommodations with a jacuzzi in Saint Michaels, MD are Inn At Perry Cabin , Parsonage Inn Bed And Breakfast and Blue Crab Lodge .

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

The best time to visit Saint Michaels is in the spring or fall, when the weather is mild and the crowds are smaller. You can also enjoy the town during the summer, but it can get hot and humid. If you're interested in seeing the fall foliage, plan your trip for October or November.

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

The best accommodations for families and kids in Saint Michaels, MD are Inn At Perry Cabin , Waterfront Property - Kayaks - Private Dock - Near Town and St - Michaels Waterfront-pool/kayak/pier/firepit .

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

The waterfront trail is a great place to walk or bike, and it offers beautiful views of the Miles River. You can also take a longer bike ride out to the Chesapeake Bay Maritime Museum, which is about 3 miles from the town center. There's a nice loop around the town, too.

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

Easton is just a short drive from Saint Michaels, and it's a great place to spend a few hours exploring. There are lots of shops and restaurants in the historic downtown area, and you can also visit the Talbot County Courthouse. If you're looking for a bigger city, Annapolis is about a 45-minute drive away. It's the capital of Maryland and home to the United States Naval Academy.

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.

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

You'll find a variety of accommodations in Saint Michaels, from cozy bed and breakfasts to luxury hotels. Many of the hotels have swimming pools and restaurants, and some even have docks where you can moor your boat. No matter what your budget is, you're sure to find a comfortable and convenient place to stay.

Saint Michaels, MD All Lodging and Accommodation

9.6 129 reviews

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

cottage, Easton

This charming cottage is located just a short 10-minute walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, making it easy to explore the town's rich history and waterfront attractions. Guests consistently rate this comfortable vacation rental excellent for its peaceful ambiance and convenient location.
The 1400 square foot cottage can comfortably accommodate up to 5 guests in its two bedrooms and three bathrooms. Enjoy modern amenities like air conditioning, a private garden, a swimming pool, a tennis court, and a spa, perfect for relaxing and enjoying the beautiful surroundings.

9.8 164 reviews

Walk To Everything House

apartment, Easton

This vacation home is conveniently located in St. Michaels, within walking distance of the Chesapeake Bay Maritime Museum and other attractions. It has received excellent ratings for its location, cleanliness, and user experience.
The house has three bedrooms and can accommodate up to six guests. It features a fully equipped kitchen with modern appliances, multiple bathrooms, laundry facilities, and a smart TV for entertainment. Guests can also enjoy the private garden, spa, and air conditioning.

No reviews

Downtown Flat - Walk To Dining & Shops - Sleeps 4

house, Easton

This downtown Saint Michaels flat is located 10 miles from the Academy of the Arts.
This 820 square foot residence offers air conditioning, a full kitchen with a dishwasher and microwave, complimentary WiFi, and on-site parking for up to 4 guests, with an outdoor seating area and fireplace for your comfort.

9.9 15 reviews

Eastern Shore Cottage Near St. Michaels Gateway

apartment, Tilghman Island

Pot Pie Cottage, a three-bedroom rental home, is conveniently located in Talbot County, six miles from St. Michaels and a short drive from Tilghman Island, offering easy access to both towns and their attractions.
This 3-bedroom, 1-bathroom vacation rental sleeps six guests and features a fully equipped kitchen, a dedicated workspace, a Smart TV, and parking; enjoy nearby St. Michaels' shops and restaurants.

9.6 123 reviews

The Dollhouse In Central Historic St Michaels

apartment, Easton

This house is situated in the charming town of St. Michaels, within a short walk of the Chesapeake Bay Maritime Museum. It has excellent user, location, and cleanliness ratings.
With 2 bedrooms and a guest capacity of 4, this house features a spa tub, garden, and barbecue grills. It has a fully equipped kitchen, multiple bathrooms, a Smart TV, and a washing machine.

9.6 17 reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

apartment, Trappe

This Trappe vacation home, located six miles from Easton's UM Shore Medical Center and the Historical Society of Talbot County, offers easy access to the Third Haven Friends Meeting House and the Academy Art Museum.
This 2200-square-foot house features five bedrooms, three bathrooms, and accommodates eight guests with amenities including a private pool, fenced yard, and fully equipped kitchen; charcoal grills are available for outdoor cooking.

10 79 reviews

The Suite At Mostly Porches

house, Easton

This charming apartment in St. Michaels is just steps from the Auto Museum, Maritime Museum, YMCA, and a variety of restaurants. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom apartment is ideal for two guests.
The 480-square-foot apartment features a kitchen with a fridge, freezer, and microwave, as well as air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking. Laundry facilities are available upon request for longer-term renters.

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.

9.9 88 reviews

Private&cozy/3br+2ba/1mi To Town

apartment, Tilghman Island

This charming vacation rental is located just outside of Saint Michaels, offering a peaceful escape while still being within easy walking distance of the town's attractions. The property enjoys excellent ratings for user experience, location, and cleanliness.
The home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a spacious living area, a private patio, and a garden, providing everything you need for a relaxing and enjoyable stay.

9.8 17 reviews

Apartment In St. Michaels Walk To Everything!

apartment, Easton

Coco's Nest is a two-bedroom apartment located in the historic district of St. Michaels, within walking distance of galleries, museums, boutiques, and restaurants.
This Easton rental features a private parking space, a modern interior with a well-appointed bathroom and a cafe-style dining area equipped with a coffee bar, toaster oven, mini fridge, and sink.

10 2 reviews

Waterfront, Hot Tub, Elevator. Waterfowl Special!

apartment, Oxford

This waterfront dwelling is situated in Oxford, offering direct access to a sandy beach and a dock. Enjoy scenic views and the convenience of a private dock for your boat, subject to approval.
The four-bedroom apartment comfortably accommodates up to eight guests, featuring a fully equipped kitchen, a relaxing basement with a bar and Jacuzzi, and modern amenities like flat-screen TVs. Enjoy the convenience of an elevator, a hot tub, and a spacious garden for outdoor relaxation.

9.9 14 reviews

Sewell Point Bungalow

apartment, Tilghman Island

This newly remodeled home is located just a short drive from the charming town of St. Michaels, offering a peaceful retreat near Tilghman Island. The surrounding area is quiet and perfect for enjoying walks, cycling, and exploring the natural beauty of the region.
This cozy cottage comfortably accommodates up to four guests and features a fully equipped kitchen with modern appliances, a private bathroom, and air conditioning. Enjoy the convenience of parking, internet access, and a peaceful setting for a relaxing getaway.

Discover Lodgings by the Sea in Saint Michaels, MD

Plan a refreshing beach-town holiday at these seaside accommodations in Saint Michaels, MD, located just a short distance from coastal attractions.

9.5 4 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton

This apartment is located in the downtown district of St. Michaels, Maryland, offering walking access to dining, shopping, and the waterfront.
This rental features a king-sized bedroom, a pull-out sofa, a fully stocked chef's kitchen with high-end appliances, gas fireplace, smart TVs, dedicated parking for two vehicles, and in-unit laundry.

Best family friendly Saint Michaels, MD lodging

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

10 9 reviews

Captain's Cove | An Esvr Property

apartment, Easton

This waterfront vacation home in St. Michaels offers stunning views of Chesapeake Bay and is within easy reach of local attractions such as the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. It has received excellent user, location, and cleanliness ratings from previous guests.
The house has a floor area of 2730 square feet and can accommodate up to 10 guests in its 5 bedrooms. It features a private pool, fireplace, fitness center, spa tub, arcade/game room, and upscale touches like a well-equipped kitchen. Free WiFi is also available.

No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Easton

This 1-bedroom flat in downtown Easton is located just steps from the harbor, shops, and award-winning restaurants.
This family-friendly apartment offers parking for 2 vehicles, a full kitchen with a dishwasher, and air conditioning, accommodating up to 4 guests.

9.9 151 reviews

Blue Crab Lodge

apartment, Easton

This Easton apartment is located in the heart of St. Michaels, directly above a coffee shop and within walking distance of shops, restaurants, and the waterfront. The apartment boasts excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms and one bathroom, accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, parking, and internet access.

8.7 22 reviews

Sunrise Cove | An Esvr Property

apartment, Oxford

This waterfront vacation home in St. Michaels is located just 3 miles from St. Michaels Winery and within 6 miles of both the Chesapeake Bay Maritime Museum and St. Michaels Museum, offering easy access to local attractions and a peaceful waterfront setting. Guests consistently rate the property highly for its cleanliness, location, and overall experience.
The 2,520 square foot home comfortably accommodates up to 6 guests in 3 bedrooms and 2 bathrooms. This spacious vacation rental boasts a private pool, a game room, a spa tub, a fireplace, outdoor barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay for all.

Frequently Asked Questions about accommodations in Saint Michaels, MD

What are the must-see sites in or near Saint Michaels, MD?
You have to check out the Chesapeake Bay Maritime Museum, it's a great way to learn about the history of the area. The Saint Michaels Museum is also a must-see, with exhibits on the town's past. And of course, you can't miss the beautiful waterfront, with its charming shops and restaurants.
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.
How can travelers reach Saint Michaels, MD?
The easiest way to get to Saint Michaels is to drive, it's about a 90-minute drive from Baltimore and a 2-hour drive from Washington, D.C. You can also take the train to Easton and then a taxi or bus to Saint Michaels. If you're coming from further away, you can fly into Baltimore-Washington International Airport (BWI) and then rent a car.
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 outdoor activities can visitors enjoy in and around Saint Michaels, MD?
There are plenty of outdoor activities to enjoy in Saint Michaels. You can go kayaking or canoeing on the Miles River, or take a boat tour to see the local wildlife. There's also a great walking trail along the waterfront, and you can rent bikes and explore the town and surrounding countryside.
What are the best accommodations with a jacuzzi in Saint Michaels, MD?
The best accommodations with a jacuzzi in Saint Michaels, MD are Inn At Perry Cabin, Parsonage Inn Bed And Breakfast and Blue Crab Lodge.
When is the ideal time to plan a trip to Saint Michaels, MD?
The best time to visit Saint Michaels is in the spring or fall, when the weather is mild and the crowds are smaller. You can also enjoy the town during the summer, but it can get hot and humid. If you're interested in seeing the fall foliage, plan your trip for October or November.
What are the best accommodations for families and kids in Saint Michaels, MD?
The best accommodations for families and kids in Saint Michaels, MD are Inn At Perry Cabin, Waterfront Property - Kayaks - Private Dock - Near Town and St - Michaels Waterfront-pool/kayak/pier/firepit.
What are the best walking or cycling routes in Saint Michaels, MD?
The waterfront trail is a great place to walk or bike, and it offers beautiful views of the Miles River. You can also take a longer bike ride out to the Chesapeake Bay Maritime Museum, which is about 3 miles from the town center. There's a nice loop around the town, too.
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 nearby towns or cities can be explored from Saint Michaels, MD?
Easton is just a short drive from Saint Michaels, and it's a great place to spend a few hours exploring. There are lots of shops and restaurants in the historic downtown area, and you can also visit the Talbot County Courthouse. If you're looking for a bigger city, Annapolis is about a 45-minute drive away. It's the capital of Maryland and home to the United States Naval Academy.
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.
What amenities can travelers expect from accommodations in Saint Michaels, MD?
You'll find a variety of accommodations in Saint Michaels, from cozy bed and breakfasts to luxury hotels. Many of the hotels have swimming pools and restaurants, and some even have docks where you can moor your boat. No matter what your budget is, you're sure to find a comfortable and convenient place to stay.

Popular destinations

Our Favorite Lodgings with a Pool in Saint Michaels, MD

On-site pool access at your lodging in Saint Michaels, MD makes a refreshing swim the perfect way to complement a day by the water.

No reviews

Crews Quarters

house, Easton

This Easton, Maryland house rental, located in Crews Quarters, is 11 miles from the Academy of the Arts in St. Michaels and 62 miles from Baltimore/Washington International Thurgood Marshall Airport.
The 1790-square-foot property boasts three bedrooms, four bathrooms, a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and parking, comfortably accommodating up to 11 guests.

10 2 reviews

Waterfront | Pet Friendly & Close To St. Michaels

apartment, Tilghman Island

This four-bedroom, three-bathroom waterfront vacation home is located in Bozman, Maryland, a short drive from the town of St. Michaels and its attractions.
The 8-guest rental boasts a private pool, dock for crabbing and kayaking, fully equipped kitchen, and complimentary kayaks, offering easy access to the Chesapeake Bay and nearby Talbot County attractions.

10 196 reviews

True St. Michaels 6 Acre Waterfront W/heated Pool

cabin, Easton

This charming cabin is situated on a 6-acre waterfront lot just outside of Historic Downtown Saint Michaels, a quick 5-10 minute bike ride away. It has received excellent ratings for location, cleanliness, and overall experience from previous guests. The cabin offers spacious accommodation with 3,000 square feet of space and comfortably sleeps up to 8 guests. Enjoy a range of amenities including a private pool, a jacuzzi, a tennis court, and a well-equipped kitchen.

No reviews

Fairview Estate | An Esvr Property

apartment, Easton

Fairview Estate is a historic property located in Talbot County, a short drive from the charming town of Easton on Maryland's Eastern Shore. The estate offers a peaceful setting, perfect for a relaxing getaway.
This 6-bedroom, 4-bathroom home can comfortably accommodate up to 12 guests. Fairview Estate provides a fully equipped kitchen, a swimming pool, a fitness center, and a garden, offering a variety of amenities for a comfortable and enjoyable stay.

Best Saint Michaels, MD accommodation with a kitchen

9.9 35 reviews

Lovely Waterfront Cottage On 2 Acres, St. Michaels

apartment, Easton

This Easton waterfront cottage, near St. Michaels, Maryland, offers easy walking or biking access to shops and restaurants in the historic town.
The three-bedroom, two-bathroom house sleeps six, features a dock with seven feet of water depth, a full kitchen with dishwasher, air conditioning, and a garden; pets are welcome (fee applies).

10 264 reviews

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

apartment, Easton

Harbor Hideaway is a charming cottage located in the heart of Saint Michaels, just a short walk from the town's shops, restaurants, and waterfront. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and two bathrooms, offering enough space for four guests. The cottage is equipped with a kitchen, air conditioning, a private pool, a terrace, a garden, a spa, a tennis court, and parking.

9.8 57 reviews

Downtown Studio | Walk To Shops & Waterfront

apartment, Easton

This studio apartment is situated in the historic district of St. Michaels, Maryland, within walking distance of the Chesapeake Bay Maritime Museum and numerous shops and restaurants. The studio features a fully equipped kitchen, a queen-sized bed, a cozy seating area, and a smart TV, comfortably accommodating up to two guests.

10 161 reviews

Shipwrights Cottage In Town!

apartment, Tilghman Island

This historic shipwright's cottage in St. Michaels, Maryland, is a short walk from St. Michaels' shops, restaurants, and waterfront.
The two-bedroom, two-bathroom house sleeps four, features a full kitchen with fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access; a private balcony from the primary bedroom adds to its appeal.

Best Saint Michaels, MD accommodation with a balcony

10 1 review

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton

10 6 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton

10 38 reviews

Downtown St. Michaels Studio Walk To Waterfront, Dining & Shops

studio, Easton

10 42 reviews

Stay By Md's Chesapeake Bay This Father's Day! Walk To Marina, Bar & Restaurant!

apartment, Stevensville

Popular Luxury Lodgings in Saint Michaels, MD

Upscale lodgings in Saint Michaels, MD set a high standard for coastal comfort, offering premium amenities in a prime location.

9.8 37 reviews

St. Michaels Waterfront Home

apartment, Easton

Check Out Pet-Friendly Lodgings in Saint Michaels, MD

Your dog is as welcome as you are; each pet-friendly lodging near the water of Saint Michaels, MD offers dog-friendly amenities.

10 70 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville

9.8 206 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton

10 2 reviews

St. Michaels Waterfront Home With Pool

apartment, Tilghman Island

No reviews

Bankors Aweigh

house, Tilghman Island

Compare Accommodations with On-Site Dining in Saint Michaels, MD

A lodging with a restaurant in Saint Michaels, MD ensures fresh local food and coastal dishes are always on the menu.

9.8 37 reviews

St. Michaels Waterfront Home

apartment, Easton

Search cheap accommodations in Saint Michaels, MD from 100+ sites!

76 Lodgings in Saint Michaels, MD

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

Walk To Everything House

Downtown Flat - Walk To Dining & Shops - Sleeps 4

Eastern Shore Cottage Near St. Michaels Gateway

The Dollhouse In Central Historic St Michaels

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

The Suite At Mostly Porches

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

Private&cozy/3br+2ba/1mi To Town

Apartment In St. Michaels Walk To Everything!

Waterfront, Hot Tub, Elevator. Waterfowl Special!

Sewell Point Bungalow

Downtown Flat Walk To Dining & Shops Sleeps 4

Captain's Cove | An Esvr Property

Apartment ∙ 1 Bedroom ∙ 4 Guests

Blue Crab Lodge

Sunrise Cove | An Esvr Property

Crews Quarters

Waterfront | Pet Friendly & Close To St. Michaels

True St. Michaels 6 Acre Waterfront W/heated Pool

Fairview Estate | An Esvr Property

Lovely Waterfront Cottage On 2 Acres, St. Michaels

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

Downtown Studio | Walk To Shops & Waterfront

Shipwrights Cottage In Town!

Downtown St. Michaels | Porch + Pet-friendly

Downtown St. Michaels | Porch + Pet-friendly

Downtown St. Michaels Studio Walk To Waterfront, Dining & Shops

Stay By Md's Chesapeake Bay This Father's Day! Walk To Marina, Bar & Restaurant!

St. Michaels Waterfront Home

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

St. Michaels Waterfront Home With Pool

Bankors Aweigh

St. Michaels Waterfront Home