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

10 23 reviews

Bayside Bungalow Kent Island

apartment, Stevensville

This Stevensville bayside cottage is steps from the Chesapeake Bay and a short walk from the Kentmorr Restaurant and Tiki Bar.
The three-bedroom, two-bathroom home sleeps six and features a fully equipped kitchen, air conditioning, parking, and access to a community beach; enjoy its peaceful back porch with bay views and high-end finishes.

No reviews

3-bedroom Historic Vacation Home Newly Renovated In The Middle Of Oxford Md.

apartment, Oxford

This Oxford, Mississippi vacation home is conveniently located within a 15-minute walk of the Oxford Museum and Play Ball Dog Park, and within 12 miles of The Third Haven Friends Meeting House and Academy Art Museum.
This 3-bedroom, 3-bathroom house sleeps 6, boasts a fully equipped kitchen with microwave and dishwasher, in-house laundry, a cozy fireplace, outdoor barbecue grills, and a smart TV; pets are welcome.

10 192 reviews

St. Michaels Waterfront-pool/kayak/pier/firepit

house, Easton

This waterfront house is located on the Miles River in Talbot County, Maryland, just a short drive from Easton, St. Michaels, and Oxford. The house has received excellent ratings for user experience, location, and cleanliness.
The spacious 5-bedroom home can accommodate up to 10 guests and features a private pool, a pier with a boat slip, kayaks, a gas fire pit, and a fully equipped kitchen. Enjoy breathtaking views of the Miles River from nearly every room, relax in the Adirondack chairs by the water, and explore the surrounding area with ease.

9.0 2 reviews

Minutes From Downtown St. Michaels And Tilghman | Private Dock | Outdoor Dining

apartment, Tilghman Island

This newly renovated three-bedroom, three-bathroom vacation home is located in the historic fisherman's village of Tilghman Island, Maryland, on a quiet dead-end street offering waterfront access and proximity to St. Michaels Winery and Rod n Reel Charter Fishing.
The 3-bedroom, 3-bathroom house features a free-flowing floor plan, chef-inspired kitchen, oversized main suite with water views, two screened porches, a private dock, kayaks, and stand-up paddleboards for exploring the Chesapeake Bay; it comfortably sleeps six guests.

10 41 reviews

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

studio, Easton

This Easton apartment rental is centrally located, steps from Muskrat Park and Saint Mary's Square in St. Michaels, Maryland, and within a 5-minute drive of the St. Michaels Museum and St. Michaels Winery.
This one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, private balcony, free parking, Wi-Fi, and is in a smoke-free building.

9.9 22 reviews

Waterfront Cottage In Wittman Maryland

apartment, Tilghman Island

This waterfront cottage in Wittman, Maryland, offers direct shoreline access and is located near local marinas and seafood establishments.
This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and features internet, air conditioning, a full kitchen with a dishwasher, and garden access, perfect for water activities like kayaking and fishing.

9.6 126 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.

10 18 reviews

St. Michaels Waterfront Home With Private Dock

apartment, Easton

This waterfront home is located in St. Michaels, a charming town on Maryland's Eastern Shore, just a short drive from Easton. The property has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom, two-bathroom house can comfortably accommodate up to six guests. Enjoy stunning water views, a private dock, multiple outdoor spaces, and access to kayaks, a public pool, and a boat ramp.

9.8 10 reviews

Cozy, Family Friendly, Log Cabin-st. Michaels, Md

apartment, Oxford

This log lodge is located in Talbot County, Maryland, 3 miles from St. Michaels and 8 miles from Easton, offering a secluded woodland setting on acres of forest overlooking a 1-acre freshwater pond.
This family-friendly log cabin accommodates 8 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, central heat/air, and outdoor living spaces including a grill and fire pit, with nearby opportunities for wildlife observation and game walks.

9.8 55 reviews

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife

apartment, Easton

This charming cottage is located in the heart of St. Michaels, just a short walk from restaurants, shops, and other attractions. It has received excellent user ratings, making it a popular choice for travelers. This 3-bedroom, 3-bathroom home offers 1280 square feet of living space. Enjoy the fully equipped kitchen, outdoor garden, spa, and parking, perfect for relaxing after a day of exploring the area.

10 270 reviews

Sm's Premier Rental Heated Pool (Closes 10/27)

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.

9.7 19 reviews

St. Michaels Stay | Walking Distance To Downtown

apartment, Easton

This Easton apartment rental is conveniently located within walking and biking distance of St. Michaels' shops, restaurants, and waterfront.
The three-bedroom, one-bathroom unit sleeps six guests and features keyless entry, a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, parking, and pet-friendly accommodations (a $200 fee applies).

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 16 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton

This restored studio apartment is located in the central district of St. Michaels, offering easy access to shops, restaurants, cafes, and the waterfront within walking distance.
This pet-friendly studio features a queen bed, kitchenette, sitting area with French doors, modern bathroom, and WiFi, accommodating up to two guests.

Best family friendly Saint Michaels, MD lodging

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

9.5 8 reviews

Waterfront | Pet Friendly & Close To St. Michaels

house, Tilghman Island

This waterfront house on Tilghman Island offers direct creek views and is located minutes from the historic town of St. Michaels.
This pet-friendly, family-friendly rental accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a private swimming pool, a private dock for crabbing, a garden, and dual living areas for relaxation.

10 1 review

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.

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.

9.8 232 reviews

Charming Studio In The Heart Of St. Michael's, Md.

apartment, Easton

The Lucky Duck Studio is located in the heart of St. Michael's Historic District on Talbot Street, just steps from the Miles River, shops, restaurants, and other attractions. This studio apartment has earned excellent ratings for its cleanliness, location, and overall user experience.
The Lucky Duck Studio comfortably sleeps four guests with a queen-size bed and a sofa that converts into a queen-size sleeper. Amenities include a fully equipped kitchen, a claw tub, a front porch, free Wi-Fi, YouTube TV, a washer and dryer, a large closet, a fully stocked parlor, and local recommendations from the hosts.

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 6 reviews

Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

apartment, Easton

This waterfront vacation home is located near Easton, within 9 miles of Pickering Creek Audubon Center, Easton Cycle and Sport, and the Historical Society of Talbot County. The home receives a "very good" user rating, making it a popular choice for travelers. This spacious 5-bedroom house can comfortably accommodate 10 guests with its 4980 square feet of living space. The property offers a private pool, a game room, a garden, a terrace, a spa, a tennis court, and parking, as well as a fully equipped kitchen and a fireplace.

9.4 25 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.

No reviews

Quailsar Farm

house, Easton

Quailsar Farm, a five-bedroom Easton, Maryland house rental, is located three miles from the Academy of the Arts, 23 miles from Federalsburg Marina, and 25 miles from the Chesapeake Exploration Center.
This 5,070-square-foot home boasts four bathrooms, accommodates up to 19 guests, includes a private pool, and offers free Wi-Fi and parking.

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 Saint Michaels, MD accommodation with a kitchen

9.9 299 reviews

Miles Aweigh

apartment, Easton

This yacht is located on Long Haul Creek, less than a mile from St. Michaels town center, offering easy access to restaurants, shops, and the Chesapeake Maritime Museum. The property has consistently received excellent ratings for its location, cleanliness, and user experience.
The boat has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy amenities like a swimming pool, garden, and parking, as well as a fully equipped kitchen with a fridge, microwave, and dishwasher.

10 26 reviews

Downtown Retreat With Bikes, Fire Pit & Kayaks

apartment, Easton

This apartment is located a few minutes from downtown St. Michaels, providing convenient access to its shops and waterfront.
This stylish, modern dwelling sleeps four guests, features two bedrooms with en-suite bathrooms, offers complimentary bikes and on-site kayaks, and includes a fire pit and BBQ grill for outdoor enjoyment.

9.8 6 reviews

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

apartment, Oxford

This Oxford waterfront home, near Oxford Museum (1.9 miles) and Play Ball Dog Park (2.5 miles), offers easy access to St. Michaels Village and St. Michaels Winery (within 9 miles).
This 3,560-square-foot vacation rental boasts five bedrooms, four bathrooms, accommodates eight guests, and includes amenities such as a fully equipped kitchen, a spa, and a private terrace.

9.6 30 reviews

Waterfront Estate - Riverslie On The Miles River

apartment, Easton

This secluded farmhouse is located just outside of Easton, a short drive from the charming town of St. Michaels, offering a peaceful waterfront escape. The property encompasses 11 acres, providing ample space for relaxation and privacy.
The farmhouse features five bedrooms and four bathrooms, comfortably accommodating up to 10 guests. Enjoy the convenience of a modern kitchen, swimming pool, garden, and parking, as well as a range of outdoor activities like fishing, crabbing, and exploring the area by canoe or kayak.

Best Saint Michaels, MD accommodation with a balcony

10 3 reviews

Waterfront | Pet Friendly & Close To St. Michaels

apartment, Tilghman Island

9.6 27 reviews

Thorneton Point Estate

apartment, Oxford

10 1 review

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

apartment, Oxford

10 5 reviews

Minutes From Downtown Easton And St. Michaels | Pool

apartment, Oxford

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.

9.8 157 reviews

Waterfront Property, Kayaks, Private Dock, Near Town

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 3 reviews

Ferry View | An Esvr Property

apartment, Oxford

9.0 4 reviews

Private Boat Dock! Wye River Retreat In Queenstown

apartment, Grasonville

No reviews

Bay Breeze

house, Grasonville

9.5 154 reviews

Two Oysters House 2025 Remodel

apartment, 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.

9.9 151 reviews

Blue Crab Lodge

apartment, Easton

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

76 Lodgings in Saint Michaels, MD

Bayside Bungalow Kent Island

3-bedroom Historic Vacation Home Newly Renovated In The Middle Of Oxford Md.

St. Michaels Waterfront-pool/kayak/pier/firepit

Minutes From Downtown St. Michaels And Tilghman | Private Dock | Outdoor Dining

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

Waterfront Cottage In Wittman Maryland

The Dollhouse In Central Historic St Michaels

St. Michaels Waterfront Home With Private Dock

Cozy, Family Friendly, Log Cabin-st. Michaels, Md

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife

Sm's Premier Rental Heated Pool (Closes 10/27)

St. Michaels Stay | Walking Distance To Downtown

Downtown St. Michaels | Porch + Pet-friendly

Waterfront | Pet Friendly & Close To St. Michaels

The Weekender | An Esvr Property

Apartment ∙ 1 Bedroom ∙ 4 Guests

Charming Studio In The Heart Of St. Michael's, Md.

Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

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

Quailsar Farm

Skipjack House | An Esvr Property

Miles Aweigh

Downtown Retreat With Bikes, Fire Pit & Kayaks

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

Waterfront Estate - Riverslie On The Miles River

Waterfront | Pet Friendly & Close To St. Michaels

Thorneton Point Estate

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

Minutes From Downtown Easton And St. Michaels | Pool

Waterfront Property, Kayaks, Private Dock, Near Town

Ferry View | An Esvr Property

Private Boat Dock! Wye River Retreat In Queenstown

Bay Breeze

Two Oysters House 2025 Remodel

Blue Crab Lodge