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

9.9 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).

No reviews

The Eagles Nest

house, Grasonville

The Eagles Nest, a Grasonville house rental, is located in Grasonville, Maryland, approximately 25 miles from Annapolis and 17 miles from Sandy Point State Park.
This five-bedroom, four-bathroom home sleeps 27 guests and boasts a private pool, fully equipped kitchen, free Wi-Fi, parking, and proximity to Baltimore-Washington International Airport (35 miles).

No reviews

Bankors Aweigh

house, Tilghman Island

Bankors Aweigh, a 1980-square-foot house on Tilghman Island, is located 13 miles from the Academy of the Arts in Mount Pleasant and 63 miles from Baltimore/Washington International Thurgood Marshall Airport.
This four-bedroom vacation rental sleeps 15 guests and boasts a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free parking.

10 5 reviews

40' Classic Bristol Sailboat

boat, Stevensville

This Bristol B 40 Yawl accommodation is located in a protected marina on a lagoon near Stevensville, offering lagoon and nature views with direct access to sunrises and sunsets. This boat sleeps up to 3 guests and features 1 bedroom, 1 bathroom, internet, a kitchen, and parking, providing a unique waterside experience with interior teak and mahogany woodwork.

No reviews

Herons Roost

house, Tilghman Island

Herons Roost, a house in Mount Pleasant, is situated 18 miles from the Academy of the Arts and 68 miles from Baltimore-Washington International Airport.
This 2,230-square-foot dwelling accommodates up to 11 guests, offering complimentary Wi-Fi, an on-site kitchen, and free private parking, with a 10:00 AM check-out time.

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.

No reviews

The Weekender

house, Tilghman Island

The Weekender, a house in Mount Pleasant, MD, is conveniently located 16 miles from the Maryland Institute College of Art and 66 miles from Baltimore/Washington International Thurgood Marshall Airport, offering easy access to Tilghman Island and the Eastern Shore.
This one-bathroom home sleeps seven guests and features free Wi-Fi, private parking, a fully equipped kitchen, and is pet-friendly, perfect for a peaceful getaway near Tilghman Island.

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.

No reviews

Red Barn Farm

house, Tilghman Island

Red Barn Farm, located in Mount Pleasant on Tilghman Island, is 12 miles from the Academy of the Arts and 62 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 4,170-square-foot house features six bedrooms and six bathrooms, accommodating up to 23 guests, a private pool, and a fully equipped kitchen; free Wi-Fi and parking are included.

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.

10 3 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.

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.

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.

10 2 reviews

Skipjack House | An Esvr Property

apartment, Tilghman Island

Skipjack House, a single-level vacation rental, is located in St. Michaels, Maryland, offering a retreat for up to six guests.
This rental features three bedrooms, two bathrooms, a full kitchen with a fridge, microwave, and dishwasher, air conditioning, and access to a swimming pool.

Best family friendly Saint Michaels, MD lodging

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

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 short walk from the waterfront, museums, and parks. It has received excellent ratings for location, cleanliness, and overall user experience.
The charming cottage has two bedrooms and one bathroom and can accommodate up to four guests. The home features a fully equipped kitchen, a screened-in porch, a private garden, and fast Wi-Fi, making it perfect for families or groups looking to explore the area.

10 2 reviews

Minutes From Downtown St. Michaels | Pool | Dock

apartment, Tilghman Island

This stunning cedar Lindal home, recently renovated, offers a waterfront escape near St. Michaels, Maryland, providing easy access to the town's attractions like the St. Michaels Museum and Avalon Theatre.
The three-bedroom, three-bathroom rental boasts a spacious open floor plan, sleeping six guests comfortably, and features a private heated pool (18 x 38 ft, seasonal), private dock, kayaks, paddleboards, and a chef-inspired kitchen.

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.

9.7 60 reviews

Chesapeake Country Cottage: A Home Away From Home

apartment, Easton

This waterfront home sits on a 3-acre property near St. Michaels and Easton, a nationally-recognized town. Guests rave about its excellent location, cleanliness, and overall experience.
This charming apartment sleeps 6 guests and features a fully equipped kitchen, a cozy living room with a fireplace, and a large deck with a screened porch. Guests can enjoy kayaking, biking, and grilling, plus the property includes a fire pit, yard games, and a private pier with a tidal cove.

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.

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

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.

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.

8.8 3 reviews

Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock

apartment, Tilghman Island

This waterfront rental is located in St. Michaels, Talbot County, just a short drive from the Chesapeake Bay Environmental Center, Matapeake State Park, and the Chesapeake Bay Maritime Museum. The surrounding area offers a peaceful and secluded setting, perfect for a relaxing getaway.
This spacious 4-bedroom, 2-bathroom home can comfortably accommodate 8 guests. The property features a private pool, hot tub, and a large outdoor deck, making it an ideal choice for families or groups looking for a memorable vacation experience.

Best Saint Michaels, MD accommodation with a kitchen

10 39 reviews

The Cottage At Broad Creek

apartment, Tilghman Island

This waterfront cottage on Tilghman Island, Maryland's Eastern Shore, offers panoramic water views and is minutes from the historic town of St. Michaels.
The one-bedroom, one-bathroom house includes a gourmet kitchen, private dock for kayaking, sunroom, fireplace, and accommodates two guests, perfect for a relaxing getaway.

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.

9.6 17 reviews

Summer Retreat Pool, Hot Tub & Outdoor Oasis

apartment, Tilghman Island

This waterfront farmhouse is located in St. Michaels, just minutes from the town center and its shops, dining, and attractions.
The 3-bedroom, 3-bathroom home comfortably sleeps 6 guests and boasts a private pool, a fully equipped kitchen, and a private dock for enjoying the serene waterfront views.

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.

Best Saint Michaels, MD accommodation with a balcony

10 130 reviews

Kent Island Beach House - "Pink" House In Kentmorr

apartment, Stevensville

10 3 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville

10 2 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton

10 12 reviews

Saint Michaels Summer Retreat With Pool & Hot Tub

apartment, Tilghman Island

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.

No reviews

Vintage Pet-friendly Cottage | Tilghman Island

apartment, Tilghman Island

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.

No reviews

Fairview Estate | An Esvr Property

apartment, Easton

9.6 4 reviews

Downtown Oxford | Outdoor Dining | Character Filled

apartment, Oxford

8.0 2 reviews

Minutes From Downtown St. Michaels | Character Filled

apartment, Tilghman Island

9.9 46 reviews

Saint Michaels Retreat With Kayaks & Bikes

apartment, Easton

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.

No reviews

The Eagles Nest

house, Grasonville

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

76 Lodgings in Saint Michaels, MD

Lovely Waterfront Cottage On 2 Acres, St. Michaels

The Eagles Nest

Bankors Aweigh

40' Classic Bristol Sailboat

Herons Roost

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

The Weekender

Waterfront, Hot Tub, Elevator. Waterfowl Special!

Red Barn Farm

Crepe Myrtle | An Esvr Property

Downtown Flat Walk To Dining & Shops Sleeps 4

Downtown Flat - Walk To Dining & Shops - Sleeps 4

Skipjack House | An Esvr Property

The Little Anchor Cottage, St. Michaels, Md

Minutes From Downtown St. Michaels | Pool | Dock

Natures Rest On Grocelys Cove-waterfront With Pool

Chesapeake Country Cottage: A Home Away From Home

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

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

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

Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock

The Cottage At Broad Creek

Red Barn Farm | An Esvr Property

Summer Retreat Pool, Hot Tub & Outdoor Oasis

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

Kent Island Beach House - "Pink" House In Kentmorr

Relax On Kent Island In 3 Bedroom Home W/waterview

Downtown Flat Walk To Dining & Shops Sleeps 4

Saint Michaels Summer Retreat With Pool & Hot Tub

Vintage Pet-friendly Cottage | Tilghman Island

Fairview Estate | An Esvr Property

Downtown Oxford | Outdoor Dining | Character Filled

Minutes From Downtown St. Michaels | Character Filled

Saint Michaels Retreat With Kayaks & Bikes

The Eagles Nest