Choose from 34 vacation rentals located in St Michaels, Maryland. Top filters in St Michaels include Internet / Wifi, Air conditioner, and TV. Prices range from $163 to $1,350 per night. Our most popular vacation rental types near St Michaels are Hotel and RV.

Top vacation rentals in St Michaels

Harbor Hideaway-  Saint Michael's Premier In-Town Rental with a pool!
5.0
Outstanding(120 Reviews)
Cottage
 in St. Michaels
St. Michael's Premier In-Town Rental with heated pool - Pool opens 4/12/24
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

The best choice in St Michaels for Cottage, for $450 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Front of Carpenter St. Cottage
4.9
Outstanding(145 Reviews)
Cottage
 in Saint Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

Are you ready to indulge in a relaxing getaway? Our Cottage in St Michaels has everything you need for a rejuvenating stay. Treat yourself to Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
vrbo logo
View deal
Property view
4.3
Excellent(28 Reviews)
Inn
 in Saint Michaels
Inn at Perry Cabin
Garden · Pool · Pets allowed

Looking for the perfect place to call home during your trip to St Michaels? This Inn offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
booking logo
View deal
Property view
4.4
Excellent(88 Reviews)
Bed and Breakfast
 in Saint Michaels
Parsonage Inn Bed and Breakfast
Garden · Pool · Pets allowed

This attractive Bed and Breakfast in St Michaels, $167 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal

Search by amenity

Vacation rentals with internet & wifi in St Michaels

Front of house from St. Michaels harbor looking across Town Park
4.7
Outstanding(103 Reviews)
Cottage
 in Saint Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
5 guests · 2 bedrooms · 3 baths
Garden · Pool · Pets allowed

When traveling to St Michaels, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $295 per night.

$$$$
vrbo logo
View deal
Front and side of W Melson House
4.8
Outstanding(104 Reviews)
Cottage
 in St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
5 guests · 2 bedrooms · 3 baths
Garden · Pool · Pets allowed

When traveling to St Michaels, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $284 per night.

$$$$
vrbo logo
View deal
Thomas Harrison House looking from St. Michaels Town Harbor
4.5
Excellent(113 Reviews)
House
 in St. Michaels
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
9 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed

Experience vacation in St Michaels with our House, Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
house front porch
4.8
Outstanding(59 Reviews)
Cottage
 in St. Michaels
Cottage downtown on a quiet street
2 guests · 1 bedroom · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Cottage for $256 in St Michaels, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
city photo
St Michaels

St Michaels travel guide

Let us help you plan your perfect St Michaels vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in St Michaels, and more.

Frequently asked questions

What do I need to know before visiting St Michaels, MD?

Before visiting St. Michaels, Maryland, there are a few things to know.

  • It is a quaint town located in Talbot county on the Eastern Shore of Maryland.
  • It is known for its waterfront marinas, restaurants, and boutiques.
  • St. Michaels is a popular tourist destination and a great place to explore the outdoors.

St. Michaels has several attractions, such as the Chesapeake Bay Maritime Museum, the St. Michaels Winery, and the Piney Point Lighthouse. There are also plenty of outdoor activities like kayaking, fishing, and hiking. It is important to remember that the town can get busy during the summer months, so plan ahead and book your accommodation in advance.

What are the must-visit tourist attractions in St Michaels, MD?

St Michaels, MD is a beautiful coastal town with a variety of must-visit tourist attractions. Here are some of the top attractions to check out:

  • Chesapeake Bay Maritime Museum
  • St Michaels Winery
  • St Michaels Nature Trail
  • St Michaels Harbour Inn, Marina & Spa

The Chesapeake Bay Maritime Museum is a great place to learn about the town's history and see a variety of boats. St Michaels Winery is a great spot for wine enthusiasts to sample local wines. The St Michaels Nature Trail is a great way to explore the natural beauty of the area. Finally, the St Michaels Harbour Inn, Marina & Spa is a great place to relax and take in the stunning views of the harbor.

How can I get around in St Michaels, MD?

You can get around in St Michaels, MD in a variety of ways:

  • By car
  • By bike
  • By foot

There are also public transportation options available, such as the Talbot County Council on Aging's Dial-A-Ride, and the Shore Transit bus system.

Where can I find affordable accommodation in St Michaels, MD?

St Michaels, MD offers a variety of affordable accommodation options. Here are a few of the best:

  • The Inn at Perry Cabin: A luxury inn located in the heart of St Michaels and offering a range of rooms and suites.
  • The Harbour Inn and Suites: A budget-friendly hotel located on the waterfront with easy access to downtown St Michaels.
  • The Inn at the Chesapeake Bay Beach Club: A charming inn offering a range of rooms and suites, with stunning views of the Chesapeake Bay.
  • The Inn at St Michaels: An upscale inn located in the heart of St Michaels, offering a range of rooms and suites.

What is the culture like in St Michaels, MD?

St. Michaels, MD is a quaint and charming town located in Talbot County on the Eastern Shore of Maryland. It is known for its maritime heritage, seafood restaurants, and quaint shops. Here is an overview of the culture in St. Michaels:

  • Historic and maritime heritage
  • Quaint shops and eateries
  • Outdoor activities such as fishing, boating, and kayaking
  • Beautiful parks and trails
  • Friendly and welcoming locals

Is St Michaels, MD safe to travel to?

St Michaels, MD is generally safe to travel to. Here are a few tips to make sure your trip is safe and enjoyable:

  • Be aware of your surroundings.
  • Avoid traveling alone at night.
  • Follow local laws and ordinances.

What are the popular shopping destinations in St Michaels, MD?

Popular shopping destinations in St Michaels, MD include:

  • The Chesapeake Trading Company
  • The St. Michaels Winery
  • The St. Michaels Crab & Steak House
  • The St. Michaels Brewing Company

What are the best neighborhoods to visit in St Michaels, MD?

The best neighborhoods to visit in St Michaels, MD are:

  • Historic District
  • Hog Neck
  • Tilghman Island

Each neighborhood has something unique to offer, from the quaint shops and restaurants in the Historic District to the stunning waterfront views of Hog Neck and the picturesque fishing villages of Tilghman Island.

Where is St Michaels, MD?

St Michaels, MD is a small town located on the Eastern Shore of Maryland in Talbot County. It is situated at the mouth of the Miles River, just off the Chesapeake Bay. The town is known for its historic charm, and is a popular destination for sailing, fishing, and other outdoor activities.

What are the most popular vacation rental amenities in St Michaels, MD?

The most popular vacation rental amenities in St Michaels, MD, include:

  • Fully-equipped kitchens
  • Wi-Fi access
  • Outdoor living areas
  • Private pools
  • Spa services

These amenities allow visitors to enjoy the area's stunning natural beauty while also having access to modern conveniences and comforts. Fully-equipped kitchens provide the opportunity to prepare meals in the comfort and privacy of the rental, while Wi-Fi access allows visitors to stay connected with the world outside. Outdoor living areas offer a great place to relax and take in the views, while private pools and spa services provide a great way to relax and unwind.

What are the top things to do in St Michaels, MD?

St Michaels, MD is a charming waterfront town located on the Eastern Shore of Maryland. There are plenty of activities to enjoy in the area, including outdoor activities, sightseeing, and shopping. Here are some of the top things to do in St Michaels, MD:

  • Go kayaking or canoeing on the Miles River
  • Visit the Chesapeake Bay Maritime Museum
  • Take a tour of the St Michaels Winery
  • Shop for antiques at the Talbot Street Marketplace

What is the price range for rentals in St Michaels?

Vacation rentals in St Michaels have a price range between $163-$1,350. The average price for rentals in St Michaels is $286 per night.

What are the most popular vacation rental amenities in St Michaels?

  • Internet / Wifi
  • Air conditioner
  • TV

Explore near St Michaels

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring