Places to stay in Saint Michaels, MD

76 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Saint Michaels, MD place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

76 Best places to stay in Saint Michaels, MD

Best Saint Michaels, MD lodgings with a pool

Among the 76 accommodations in Saint Michaels, MD, here are the 4 best ones with a pool

Bankors Aweigh - Saint Michaels, MD
No reviews

Bankors Aweigh

house, Tilghman Island
This Tilghman Island holiday home is located 21 kilometres from the Academy Of The Arts in Mount Pleasant and 101 kilometres from Baltimore-Washington International Airport.
This detached property offers accommodation for up to 15 guests across four bedrooms, featuring a private swimming pool, hot tub, Wi-Fi, parking, and a fully equipped kitchen.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

house, Trappe
This substantial Trappe dwelling is located within the district, offering straightforward access to the Academy of the Arts, 8.9 kilometres away, and within driving distance of Federalsburg Marina, 40.2 kilometres away, and the Chesapeake Exploration Centre, 48.3 kilometres away.
This property spans 204 square metres and features four bedrooms, three bathrooms, and accommodates up to 15 guests, with amenities including air conditioning, WiFi, a private swimming pool, a terrace, and on-site parking, alongside a strict no-party policy.
Kent Island Waterfront | Game Room | Private Dock | Pool - Saint Michaels, MD
10 3 reviews

Kent Island Waterfront | Game Room | Private Dock | Pool

apartment, Grasonville
This five-bedroom Grasonville waterfront house, in Queen Anne's County, Maryland, offers easy access to attractions such as St. Michaels and Easton (distances unspecified).
The colonial-style property boasts a chef's kitchen, four bathrooms, a private dock on Little Greenwood Creek, a swimming pool (open 15 May – 15 October), and accommodates up to 14 guests.
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, situated near St. Michaels on Tilghman Island's Eastern Shore, offers breathtaking Broad Creek waterfront views and is a short drive from St. Michaels Museum and Avalon Theatre.
Sleeping up to six guests, this three-bedroom, three-bathroom property boasts a chef-inspired kitchen, private heated pool (seasonal, 15 May – 15 October), private dock, kayaks, paddleboards, and expansive entertainment areas including a wrap-around porch and propane fire pit.

Best family friendly Saint Michaels, MD lodging

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

Red Barn Farm | An Esvr Property - Saint Michaels, MD
10 1 review

Red Barn Farm | An Esvr Property

apartment, Tilghman Island
This recently remodelled six-bedroom waterfront property in St. Michaels, Talbot County, Maryland, offers easy access to the Chesapeake Bay and is situated near the town's restaurants and historical sites, though the precise distance isn't specified.
The 6-bedroom, 5.5-bathroom house boasts a chef's kitchen with dual ovens and a wine fridge, accommodating up to twelve guests and featuring a spacious open-plan layout, a swimming pool, and a garden.
Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD
9.6 8 reviews

Downtown Oxford | Outdoor Dining | Character Filled

apartment, Oxford
This 3-bedroom holiday home is located in a peaceful Oxford neighbourhood, within walking distance of waterfront restaurants, shops and parks, and a short drive to St. Michaels and Tilghman Island. The property is a short drive from the centre of Oxford and is ideal for families or groups of friends looking for a relaxing getaway.
The apartment is 140 square metres and has a spacious layout, making it perfect for groups of up to 6 guests. The apartment offers a range of amenities, including a large deck, a propane grill, a fully equipped kitchen, Wi-Fi access, and a landscaped garden.
Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Golf Cours - Saint Michaels, MD
10 2 reviews

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

apartment, Easton
This Easton waterfront property, near Bruffs Island, Pickering Creek Audubon Center, and the Talbot County Historical Society (all within 14.5km), offers stunning water views and direct water access.
This six-bedroom, six-bathroom holiday home boasts 557 square metres of space, a private pool, fitness centre, tennis court, and accommodates up to twelve guests, providing convenient self-catering with a fully equipped kitchen and laundry facilities.
Minutes From Downtown St. Michaels | Character Filled - Saint Michaels, MD
8.0 2 reviews

Minutes From Downtown St. Michaels | Character Filled

apartment, Tilghman Island
This two-bedroom holiday home in Bozman, a five-minute (8 km) drive from St. Michaels, offers easy access to the town's waterfront restaurants and shops.
The property features a spacious open-plan layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, patio, yard games, and bikes, plus air conditioning and Wi-Fi.

Frequently asked questions about accommodations in Saint Michaels, MD

  • What outdoor activities can visitors enjoy in and around Saint Michaels, MD?

    Saint Michaels is a great place for watersports, with plenty of opportunities for sailing, kayaking, and fishing. If you're looking for something a bit more relaxed, you can always take a walk or bike ride along the scenic waterfront. There's also a beautiful state park just a short drive away, with hiking trails and a beach.
  • 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.

  • When is the ideal time to plan a trip to Saint Michaels, MD?

    Spring and autumn are the best times to visit Saint Michaels, the weather is mild and the crowds are smaller. Summer can be hot and humid, but it's a great time to enjoy the beaches and watersports. Winter can be chilly, but there's still plenty to see and do, especially if you enjoy the quieter side of things.
  • 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 nearby towns or cities can be explored from Saint Michaels, MD?

    Easton is a charming town about a 20-minute drive away, with a thriving arts scene and plenty of shops and restaurants. Annapolis, the capital of Maryland, is about an hour's drive away and is a great place to explore history and culture. And of course, you can always take a day trip to Baltimore or Washington D.C., both of which are within a two-hour drive.
  • What are the best accommodations with a jacuzzi in Saint Michaels, MD?

  • What amenities can travelers expect from accommodations in Saint Michaels, MD?

    There are a variety of accommodations in Saint Michaels, from charming bed and breakfasts to luxury hotels. Most accommodations offer amenities such as free Wi-Fi, parking, and breakfast. Some also have pools, fitness centers, and restaurants.
  • What are the best accommodations for families and kids in Saint Michaels, MD?

  • 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 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.

Popular destinations

Best Saint Michaels, MD accommodations 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
This Stevensville beach house is located just 14.5 kilometres from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to the area's attractions. It has consistently received excellent ratings for user experience, location, and cleanliness.
This four-bedroom property spans 167 square metres and comfortably accommodates up to 14 guests. The house provides a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.
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
This Stevensville holiday home on Kent Island offers a tranquil waterside retreat, situated 35 kilometres from Annapolis Harbour and 51 kilometres from Baltimore-Washington International Airport.
This spacious 138 square metre property accommodates up to 21 guests with four bedrooms, three bathrooms, a fully equipped kitchen, a living room, and outdoor space including a garden and patio, complemented by free private parking and WiFi.
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 waterfront flat on Porters Creek, Tilghman Island, offers direct water access and is located a mere few minutes from St. Michaels' restaurants, shops, and museums.
This property, accommodating up to six guests, boasts three bedrooms, two bathrooms, a private pool, hot tub, fire pit, and a private dock for fishing and crabbing.
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
This waterfront apartment is located in McDaniel, just 3km from the town of St. Michaels, offering a peaceful retreat while still being close to local attractions. The apartment is ideal for families or groups of friends, with 3 bedrooms and 4 bathrooms, comfortably accommodating up to 6 guests.
The apartment boasts a modern and spacious interior with a fully equipped kitchen, a private swimming pool, and a jacuzzi, perfect for relaxing after a day exploring the island. Guests can also enjoy stunning views from the terrace or balcony, and take advantage of the shared dock for swimming, kayaking, or simply soaking up the sun.

Best Saint Michaels, MD accommodations with a kitchen

Lovely Waterfront Cottage On 2 Acres, St. Michaels - Saint Michaels, MD
9.9 35 reviews

Lovely Waterfront Cottage On 2 Acres, St. Michaels

apartment, Easton
This Easton holiday home is situated near St. Michaels, Maryland, within a short walk or cycle ride (approximately 1.6 km) of its shops and restaurants.
Sleeping six, this three-bedroom, two-bathroom property boasts a kitchen with dishwasher, air conditioning, a garden, and Wi-Fi; a private dock offering 2.1 metres of water depth is also available for boating enthusiasts.
Dr. Miller House. Best Location-in The Heart Town - Saint Michaels, MD
9.8 219 reviews

Dr. Miller House. Best Location-in The Heart Town

apartment, Easton
This charming apartment is situated in a delightful district of Easton, just 0.8 kilometres from the waterfront and within easy walking distance of shops, restaurants, a winery, brewery, and coffee shops. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment is a two-bedroom, one-bathroom property with a maximum capacity of six guests. It features a modern kitchen equipped with a fridge, microwave oven, and dishwasher, as well as air conditioning, a garden, parking, and internet access.
Herons Roost - Saint Michaels, MD
No reviews

Herons Roost

house, Tilghman Island
This air-conditioned dwelling on Tilghman Island is located 109 kilometres from Baltimore-Washington International Airport and 29 kilometres from the Academy of the Arts.
This 207 square metre house offers accommodation for up to 11 guests, featuring a well-equipped kitchen with a fridge, microwave oven and dishwasher, complimentary Wi-Fi, and private on-site parking.
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 flat is located in St. Michaels, Talbot County, just a short distance from the Chesapeake Bay Environmental Center and Matapeake State Park, offering a peaceful escape from the hustle and bustle. The flat is situated in a tranquil rural setting, close to local attractions such as the St. Michaels Museum and the Chesapeake Bay Maritime Museum.
The spacious four-bedroom flat, covering 184 square metres, comfortably accommodates up to eight guests. This property offers a range of amenities including a private pool and hot tub, a well-equipped kitchen, and a large outdoor deck, perfect for relaxing and enjoying the beautiful surroundings.
©2026 cozycozy.com