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Saint Michaels, MD accommodations
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76 Lodgings in Saint Michaels, MD

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.

Skipjack House | An Esvr Property - Saint Michaels, MD
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

The Little Anchor Cottage, St. Michaels, Md - Saint Michaels, MD
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.
Minutes From Downtown St. Michaels | Pool | Dock - Saint Michaels, MD
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.
Natures Rest On Grocelys Cove-waterfront With Pool - Saint Michaels, MD
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.
Chesapeake Country Cottage: A Home Away From Home - Saint Michaels, MD
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?

  • 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.

Grandview - Cottage 1b, Queen Bed, Pool, Bay, Wifi - Saint Michaels, MD
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.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
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.
Minutes From Downtown St. Michaels | Pool | Kayaks | 350 Ft Of Shoreline | Luxur - Saint Michaels, MD
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.
Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock - Saint Michaels, MD
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

The Cottage At Broad Creek - Saint Michaels, MD
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.
Red Barn Farm | An Esvr Property - Saint Michaels, MD
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.
Summer Retreat  Pool, Hot Tub & Outdoor Oasis - Saint Michaels, MD
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.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
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

Kent Island Beach House - "Pink" House In Kentmorr - Saint Michaels, MD
10 130 reviews

Kent Island Beach House - "Pink" House In Kentmorr

apartment, Stevensville
Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 3 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville
Downtown Flat  Walk To Dining & Shops  Sleeps 4 - Saint Michaels, MD
10 2 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

apartment, Easton
Saint Michaels Summer Retreat With Pool & Hot Tub - Saint Michaels, MD
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.

Vintage Pet-friendly Cottage | Tilghman Island - Saint Michaels, MD
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.

Fairview Estate | An Esvr Property - Saint Michaels, MD
No reviews

Fairview Estate | An Esvr Property

apartment, Easton
Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD
9.6 4 reviews

Downtown Oxford | Outdoor Dining | Character Filled

apartment, Oxford
Minutes From Downtown St. Michaels | Character Filled - Saint Michaels, MD
8.0 2 reviews

Minutes From Downtown St. Michaels | Character Filled

apartment, Tilghman Island
Saint Michaels Retreat With Kayaks & Bikes - Saint Michaels, MD
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.

The Eagles Nest - Saint Michaels, MD
No reviews

The Eagles Nest

house, Grasonville
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