Choose from 31 vacation rentals located in Saint Michaels, Maryland. Top filters in Saint Michaels include Internet / Wifi, Air conditioner, and Parking. Prices range from $252 to $2,269 per night. Our most popular vacation rental types near Saint Michaels are Apartment and Hotel.

Top vacation rentals in Saint Michaels

Outdoor dining
4.9
Outstanding(165 Reviews)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Cottage
 in Saint Michaels
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

Are you ready to indulge in a relaxing getaway? Our Cottage in Saint 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.

$$$$
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Property view
4.5
Excellent(44 Reviews)
Inn at Perry Cabin
Inn
 in Saint Michaels
1 king bed
Garden · Pool · Pets allowed

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

$$$$
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Property view
4.0
Good(20 Reviews)
George Brooks House B&B
Bed and Breakfast
 in Saint Michaels
1 queen bed
Garden · Pool · Pets allowed

Looking for a Bed and Breakfast in Saint Michaels, this Bed and Breakfast for $252 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Property view
4.4
Excellent(63 Reviews)
Parsonage Inn Bed and Breakfast
Bed and Breakfast
 in Saint Michaels
1 queen bed
Garden · Pool · Pets allowed

This attractive Bed and Breakfast in Saint Michaels, $259 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Vacation rentals with internet & wifi in Saint Michaels

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Fridge, microwave, oven, stovetop
5.0
Outstanding(129 Reviews)
St. Michael's Premier In-Town Rental with heated pool - Pool is open!
Cottage
 in St. Michaels
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

The best choice in Saint Michaels for Cottage, for $918 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property grounds
4.8
Outstanding(111 Reviews)
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Cottage
 in Saint Michaels
5 guests · 2 bedrooms · 3 baths
Garden · Pool · Pets allowed

When traveling to Saint Michaels, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $448 per night.

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Marina
4.8
Outstanding(114 Reviews)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Cottage
 in St Michaels
5 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed
Most favorited

When traveling to Saint Michaels, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $387 per night.

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Exterior
4.7
Outstanding(121 Reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
House
 in St. Michaels
9 guests · 7 bedrooms · 4 baths
Garden · Pool · Pets allowed

Experience vacation in Saint 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.

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Saint Michaels

Saint Michaels travel guide

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

Vacation rentals in Saint Michaels have a price range between $252-$2,269. The average price for rentals in Saint Michaels is $374 per night.

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

  • Internet / Wifi
  • Air conditioner
  • Parking

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