Vacation Rentals in Saint Michaels, MD

54 available vacation rental offers

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

54 Holiday rentals and Airbnb in Saint Michaels, MD

Highly-Rated Holiday Rentals for Families in Saint Michaels, MD, United States

Give the kids instant access to beach fun and wide-open spaces to unwind at family holiday rentals in Saint Michaels, MD, United States.

Large -In Town- Historic House On Harbor In St Michaels - Walk To Everything! - Saint Michaels, MD
9.5 239 reviews

Large -In Town- Historic House On Harbor In St Michaels - Walk To Everything!

apartment, Easton
The Thomas Harrison House is situated in the centre of St. Michaels, just a short walk from the town's museums, shops, restaurants and park, offering a convenient location for exploring this charming waterfront town. The property consistently receives excellent ratings for its location, cleanliness and overall experience.
The house spans 242 square metres and comfortably accommodates up to 9 guests in its six bedrooms, making it ideal for families or groups. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a spa, a garden and a terrace, providing ample opportunities for relaxation and enjoyment.
Waterfront Property, Kayaks, Private Dock, Near Town - Saint Michaels, MD
9.8 156 reviews

Waterfront Property, Kayaks, Private Dock, Near Town

apartment, Easton
This waterfront holiday home is located just three miles from St. Michaels Winery and Museum, offering easy access to local attractions and a peaceful setting. The property has received excellent guest ratings, indicating a high standard of comfort and service.
The home features three bedrooms and three bathrooms, providing ample space for up to six guests. A range of amenities are available, including a swimming pool, spa, garden, and barbecue facilities, ensuring a relaxing and enjoyable stay.
Waterfront Estate - Riverslie On The Miles River - Saint Michaels, MD
9.6 30 reviews

Waterfront Estate - Riverslie On The Miles River

apartment, Easton
This secluded farmhouse is located 18 kilometres outside of Easton and 15 kilometres from St. Michaels, offering a peaceful retreat surrounded by water and 11 acres of private land. The farmhouse is perfect for a family getaway or a group of friends looking to enjoy a tranquil escape.
The five-bedroom, four-bathroom farmhouse can accommodate up to 10 guests, offering plenty of space for everyone to relax and enjoy the amenities. Guests can take advantage of the private pool, the fully-equipped kitchen, the spacious living areas, and the two docks for crabbing and fishing.
Cozy 2br Home Near Idlewild Park - Saint Michaels, MD
10 9 reviews

Cozy 2br Home Near Idlewild Park

apartment, Easton
This Easton holiday home is conveniently located within 1.6km of The Third Haven Friends Meeting House, the Academy of the Arts, the Academy Art Museum, the Customs House, and the Talbot County Visitor Centre.
This pet-friendly, family-friendly property sleeps four guests in two bedrooms and one bathroom, offering free Wi-Fi, a fully equipped kitchen including a dishwasher, in-house laundry facilities, and on-site parking.

Find the Best Holiday Rentals with a Swimming Pool in Saint Michaels, MD, United States

Walk straight out of your kitchen and plunge into a crystal-clear, private swimming pool at island holiday rentals in Saint Michaels, MD, United States.

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 133 reviews

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.
Saint Michaels Summer Retreat With Pool & Hot Tub - Saint Michaels, MD
10 13 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.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
9.4 25 reviews

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

apartment, Tilghman Island
This waterfront property on Porters Creek, a peaceful peninsula minutes from the historic town of St. Michaels, offers direct access to the Chesapeake Bay.
The three-bedroom, two-bathroom dwelling boasts a gourmet kitchen, private pool and spa, covered deck, fire pit, and dock for kayaking and crabbing, accommodating up to six guests.
Summer Retreat  Pool, Hot Tub & Outdoor Oasis - Saint Michaels, MD
9.7 20 reviews

Summer Retreat Pool, Hot Tub & Outdoor Oasis

apartment, Tilghman Island
This freshly remodelled 2024 waterfront farmhouse in Talbot County, Maryland, is situated approximately 16km from Saint Michaels, offering easy access to its shops and restaurants.
This three-bedroom, three-bathroom property sleeps six guests and boasts a private pool, hot tub, extensive grounds, a fully equipped kitchen including a dishwasher, and complimentary internet access; pets are welcome (surcharge applies).

Frequently asked questions about holiday rentals in Saint Michaels, MD

  • What are some interesting places to visit in or near Saint Michaels, MD?

    Saint Michaels is a charming town with plenty to see. The Chesapeake Bay Maritime Museum is a must-visit, showcasing the region's rich maritime history. For stunning views, head to the St. Michaels Harbour Inn Marina, or take a stroll along the waterfront. Just a short drive away, you can explore the historic town of Easton, with its quaint shops and restaurants.
  • What are the best Airbnb and holiday rentals in Saint Michaels, MD?

    Stay In The Heart Of Saint Michaels, Waterfront Property - Kayaks - Private Dock - Near Town and Walk To Everything House are among the best Airbnb and holiday rentals in Saint Michaels, MD.

  • Which walking or cycling routes are the best in Saint Michaels, MD?

    The town is very walkable, with plenty of charming streets to explore. For a scenic walk, try the 3.2km Chesapeake Bay Trail, which offers beautiful views of the water. If you're into cycling, the 11km Miles River Bikeway is a great option, taking you through picturesque countryside.
  • What are the most popular Airbnbs in Saint Michaels, MD?

  • What sports or outdoor activites can visitors enjoy in and around Saint Michaels, MD?

    Sailing and kayaking are popular activities in the area. The Chesapeake Bay is a haven for watersports, and you can find plenty of rental options in town. If you prefer to stay on land, there are several golf courses nearby, as well as hiking trails in the surrounding forests.
  • What are the best holiday rentals with a pool in Saint Michaels, MD?

  • What other towns or cities can be easily accessed from Saint Michaels, MD?

    Saint Michaels is conveniently located within a short drive of several other interesting towns and cities. Easton, with its historic district and vibrant arts scene, is just 15 minutes away. The larger city of Annapolis, the capital of Maryland, is about an hour's drive.
  • What are the best rentals for families and kids in Saint Michaels, MD?

  • What amenities are commonly available in vacation rentals in Saint Michaels, MD?

    Vacation rentals in Saint Michaels usually come equipped with modern amenities like Wi-Fi, air conditioning, and laundry facilities. Many also offer private decks or patios, perfect for enjoying the beautiful surroundings. Some even have access to private docks or swimming pools.
  • What are the best rentals or Airbnbs with a jacuzzi in Saint Michaels, MD?

    The best holiday rentals or Airbnb with a jacuzzi in Saint Michaels, MD are Beautiful Waterfront Home W\/ Pool In St - Michaels, Blue Crab Lodge and Watch The Ever-changing Sunset Reflect Over The Eastern Bay.

  • What time of year is best to rent a vacation rental Saint Michaels, MD?

    Spring and autumn are popular times to visit Saint Michaels, with mild temperatures and fewer crowds. Summer can get hot and humid, but it's a great time to enjoy the water. If you're looking for a quieter experience, consider visiting during the winter months, when the town has a charming, festive atmosphere.
  • What are the local dishes in Saint Michaels, MD region?

    The Chesapeake Bay is famous for its seafood, and Saint Michaels is no exception. Try the local crab cakes, a true delicacy, or sample the fresh oysters, which are a local favourite. You can't go wrong with a classic Maryland crab soup, a hearty and flavorful dish.

Popular destinations

Find Holiday Rentals with Balconies in Saint Michaels, MD, United States

Wake up to the soothing sight of the blue ocean right from your private rental balcony in Saint Michaels, MD, United States.

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.
Downtown St. Michaels Studio  Walk To Waterfront, Dining & Shops - Saint Michaels, MD
10 40 reviews

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

studio, Easton
This St. Michaels apartment, a short distance from Muskrat Park and St Mary's Square, offers easy access to St. Michaels Museum and St. Michaels Winery, all within a 5-minute radius (approximately 0.8km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen with dishwasher, private balcony, parking, and Wi-Fi; enjoy nearby attractions such as the St Mary's Square Museum.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
10 10 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.
Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K - Saint Michaels, MD
9.8 6 reviews

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

apartment, Easton
This waterfront holiday home is located just 9 miles from Easton's Pickering Creek Audubon Center, Easton Cycle and Sport, and the Historical Society of Talbot County, offering easy access to local attractions. The property has received very good user ratings, indicating a comfortable and enjoyable stay.
The house offers 5 bedrooms and 5 bathrooms, comfortably accommodating up to 10 guests in its 463 square meters of space. Enjoy a private pool, a tennis court, a spa, a garden, and a terrace, along with a well-equipped kitchen and a fireplace for a luxurious experience.

Best Saint Michaels, MD holiday rentals with parking

Easton Getaway! - Saint Michaels, MD
10 5 reviews

Easton Getaway!

apartment, Easton
This modern farmhouse is situated on the Eastern Shore, a 16-kilometre drive from Easton town centre and a 24-kilometre drive from St. Michaels. The property offers four bedrooms, three bathrooms, and a spacious open-plan layout, with a kitchen featuring a fridge, freezer, microwave oven, and dishwasher, as well as a private garden, swimming pool, and parking.
Downtown Oxford | Charming | Pet Friendly - Saint Michaels, MD
9.8 44 reviews

Downtown Oxford | Charming | Pet Friendly

apartment, Oxford
This charming cottage is situated in the historic town of Oxford, a short walk from parks, restaurants, and the local produce stand. It has received excellent user ratings, making it a popular choice for travellers.
The property offers three bedrooms and two bathrooms, spanning 164 square metres. It comes with a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and internet access, making it perfect for a comfortable and enjoyable stay.
Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien - Saint Michaels, MD
9.8 6 reviews

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

apartment, Oxford
This luxurious five-bedroom waterfront property near Oxford is situated approximately 3km from the Oxford Museum and 4km from Play Ball Dog Park, offering scenic views and easy access to St Michael's Village and St Michael's Winery within a 14.5km radius.
Boasting 331 square metres of floor space, this self-catering house sleeps eight guests and includes four bathrooms, a complete kitchen with dishwasher, a terrace, garden, spa, parking, and free Wi-Fi.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.6 18 reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

apartment, Trappe
This Trappe holiday home, situated within 9.6km of the Third Haven Friends Meeting House, Academy Art Museum, and Academy of the Arts, offers convenient access to local attractions and amenities.
This five-bedroom, three-bathroom property boasts 204 square metres of living space, including a private pool, fully equipped kitchen, and can comfortably accommodate eight guests.

Your Pick of Premium Coastal Stays in Saint Michaels, MD, United States

Find luxury holiday rentals in Saint Michaels, MD, United States for a premium island escape.

Whitehall Acres | An Esvr Property - Saint Michaels, MD
10 1 review

Whitehall Acres | An Esvr Property

apartment, Easton

Find Holiday Rentals in the CBD of Saint Michaels, MD, United States

Stay just steps away from local boutiques, seafood spots, and the sand at holiday rentals in the heart of Saint Michaels, MD, United States.

Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
10 2 reviews

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton
Dollhouse In Central Historic St Michaels - Saint Michaels, MD
9.6 125 reviews

Dollhouse In Central Historic St Michaels

apartment, Easton
Large -In Town- Historic House On Harbor In St Michaels - Walk To Everything! - Saint Michaels, MD
9.5 239 reviews

Large -In Town- Historic House On Harbor In St Michaels - Walk To Everything!

apartment, Easton
Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Saint Michaels, MD
9.6 291 reviews

Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town

cottage, Easton

Find Holiday Rentals by the Sea in Saint Michaels, MD, United States

Walk directly out of your living room straight onto the soft sand at seashore holiday rentals in Saint Michaels, MD, United States.

Spacious Waterfront House In Charming Royal Oak With Wifi, Ac, Dock - Saint Michaels, MD
8.4 5 reviews

Spacious Waterfront House In Charming Royal Oak With Wifi, Ac, Dock

cottage, Oxford
Cottage At Goose Neck Point - Saint Michaels, MD
10 16 reviews

Cottage At Goose Neck Point

cottage, Oxford
Loon Cottage On Irish Creek - Saint Michaels, MD
10 3 reviews

Loon Cottage On Irish Creek

apartment, Oxford
Minutes From Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock - Saint Michaels, MD
10 16 reviews

Minutes From Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock

apartment, Tilghman Island

Find Holiday Rentals with a Jacuzzi in Saint Michaels, MD, United States

Check out holiday rentals with a hot tub in Saint Michaels, MD, United States for beachside indulgence.

Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator! - Saint Michaels, MD
9.4 18 reviews

Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

apartment, Oxford
Waterfront Family Retreat - Mins From St. Michaels - Saint Michaels, MD
10 5 reviews

Waterfront Family Retreat - Mins From St. Michaels

apartment, Oxford
Waterfront, Hot Tub, Elevator. Waterfowl Special! - Saint Michaels, MD
10 2 reviews

Waterfront, Hot Tub, Elevator. Waterfowl Special!

apartment, Oxford
©2026 cozycozy.com