Vacation Rentals in Saint Michaels, MD

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Saint Michaels, MD holiday rentals
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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.

Private Pool & Stunning Bay Views On Kent Island - Saint Michaels, MD
9.2 63 reviews

Private Pool & Stunning Bay Views On Kent Island

apartment, Stevensville
This Stevensville holiday home is ideally situated within 14.5km of Matapeake State Park, Romancoke Wharf County Park, and Paul Reed Smith Guitars.
This 185 square metre property boasts three bedrooms, a sofa bed, three bathrooms, a fully equipped kitchen, private pool, barbecue facilities, on-site laundry, and accommodates up to twelve guests.
Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Luxury - Saint Michaels, MD
10 1 review

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

apartment, Oxford
This five-bedroom house, ideal for families, is located in Royal Oak, Maryland, approximately 15km from Saint Michaels Village and its museums, and within 20km of the Chesapeake Bay Maritime Museum and Saint Mary's Square.
The 632 square metre property boasts a private pool, fitness centre, tennis court, and spa, accommodating up to 10 guests and offering a fully equipped kitchen, free Wi-Fi, and ample 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 apartment is located just a short drive from the historic towns of St. Michaels and Easton, offering a peaceful setting in a beautiful area. It has excellent user, location, and cleanliness ratings, making it a great option for travellers.
This charming home has three bedrooms and one bathroom, accommodating up to six guests. It offers a range of amenities, including a fully equipped kitchen, a living room with a wood-burning fireplace, a spacious outdoor area with a deck and a screened porch, a private pier and tidal cove, and a selection of recreational equipment such as kayaks, bicycles, and yard games.
Artists, Writers & Creative Minds  Imagine Your Getaway At Simplicity Cottage - Saint Michaels, MD
9.8 22 reviews

Artists, Writers & Creative Minds Imagine Your Getaway At Simplicity Cottage

cottage, Tilghman Island
Simplicity Cottage is situated on Tilghman Island, a short distance from the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum, offering a peaceful retreat surrounded by the scenic Chesapeake Bay. This charming holiday home is perfect for a small family or group of friends seeking a relaxing getaway.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a waterfront location with a substantial dock, air conditioning, internet access, and a spacious lot perfect for outdoor activities and entertaining.

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.

Newly Renovated Modern Waterfront Home - Saint Michaels, MD
10 43 reviews

Newly Renovated Modern Waterfront Home

apartment, Easton
This newly renovated riverside mansion is situated in Easton, just a short distance from the town centre and offering stunning views across the water. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The home has five bedrooms and five bathrooms, comfortably accommodating up to 15 guests. Enjoy a range of amenities including a swimming pool, fitness centre, and a spacious garden, perfect for relaxing or entertaining.
Tilghman | Pool | Private Dock | Pet Friendly - Saint Michaels, MD
8.0 2 reviews

Tilghman | Pool | Private Dock | Pet Friendly

apartment, Tilghman Island
This waterfront flat on Knapps Narrows, Tilghman Island, Maryland, offers direct access to the Chesapeake Bay with a private dock and water views, situated moments from Knapp's Narrows Marina & Inn and Tilghman Island Marina, and a short drive to St. Michaels and Easton.
This spacious 286 square metre residence accommodates up to eight guests with four bedrooms and three bathrooms, featuring a private outdoor swimming pool, kayaks, a Solo Stove fire pit, a propane grill, and a substantial private garden, perfect for exploring the surrounding waterways and enjoying al fresco dining.
Waterfront Cottage Retreat On 18 Acre Farm, Pool - Saint Michaels, MD
10 15 reviews

Waterfront Cottage Retreat On 18 Acre Farm, Pool

apartment, Oxford
This four-bedroom cottage is situated on an 18-acre waterfront estate, just a short distance from the historic towns of Easton and St Michaels, offering a tranquil escape. The property boasts a private swimming pool, tennis court, fitness centre, and a host of other amenities, including a petting zoo and art barn, making it ideal for families or groups seeking a relaxing and enjoyable stay.
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.

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.

Charming 3-bedroom  In Village Of Claiborne  Book 3 Nights Get 4th Free Strn26-6 - Saint Michaels, MD
10 1 review

Charming 3-bedroom In Village Of Claiborne Book 3 Nights Get 4th Free Strn26-6

apartment, Claiborne
This three-bedroom house in Claiborne, a short drive from St. Michaels, offers easy access to the Chesapeake Bay Maritime Museum and St. Michaels Museum, both within a few kilometres.
The property sleeps six, includes WiFi and air conditioning, and is close to the Phillips Wharf Environmental Center and Paul Reed Smith Guitars, providing a relaxing base for exploring Tilghman Island.
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.
New! Savor Bay Sunsets With Fire Pit In Stevensville - Saint Michaels, MD
No reviews

New! Savor Bay Sunsets With Fire Pit In Stevensville

apartment, Stevensville
This spacious Kent Island apartment in historic Stevensville offers a peaceful Eastern Shore experience, situated on a lake just 3 kilometres from Stevensville's attractions and 7 kilometres from Terrapin Nature Park.
This 168 square metre residence accommodates up to 8 guests, featuring a full kitchen with an island, Wi-Fi, in-home laundry, outdoor seating with a fire pit, and driveway parking for 4 cars.
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.

Best Saint Michaels, MD holiday rentals with parking

Neavitt Cottage - Saint Michaels, MD
No reviews

Neavitt Cottage

house, Tilghman Island
Neavitt Cottage, situated in Neavitt, Maryland, is approximately 32 kilometres from the Maryland Institute College of Art and 113 kilometres from Baltimore/Washington International Thurgood Marshall Airport.
This two-bathroom property offers 171 square metres of space, sleeping up to 15 guests, with a fully equipped kitchen, free Wi-Fi, parking, and pet-friendly accommodation; nearby activities include boating, fishing, and crabbing in the Chesapeake Bay.
Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.6 49 reviews

Cottage #6 Oar & Anchor Cottage

cottage, Tilghman Island
This charming cottage is situated on Tilghman Island, just a short distance from the town and its community pool. It has consistently received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage comfortably sleeps four guests in one bedroom and one bathroom. Guests can enjoy a fully equipped kitchen, outdoor amenities such as a fire pit and corn hole, and the option to rent boats and go fishing or crabbing.
House On The Bay With Private Beach Access & Panoramic Bridge Views - Saint Michaels, MD
9.6 24 reviews

House On The Bay With Private Beach Access & Panoramic Bridge Views

apartment, Stevensville
This Stevensville beach house boasts direct water access and lies within 14.5km of Matapeake State Park, Romancoke Wharf County Park, and under 19km from Love Point State Park.
The three-bedroom property, sleeping six, offers a fully equipped kitchen, private patio, garden, spa, parking, and free Wi-Fi; nearby activities include exploring the three aforementioned parks.
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.

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.

Heated Pool, Sandy Beach, Pier, And Playground Set Punch Point Apart! - Saint Michaels, MD
10 14 reviews

Heated Pool, Sandy Beach, Pier, And Playground Set Punch Point Apart!

apartment, Sherwood

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.

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

Downtown St. Michaels | Porch + Pet-friendly

apartment, Easton
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 138 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
Carpenter St. Cottage In Town St. Michaels! - Saint Michaels, MD
9.7 94 reviews

Carpenter St. Cottage In Town St. Michaels!

apartment, 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.

Stay By Md's Chesapeake Bay! Walk To Marina, Beach Bar & Restaurant! - Saint Michaels, MD
10 43 reviews

Stay By Md's Chesapeake Bay! Walk To Marina, Beach Bar & Restaurant!

apartment, Stevensville
Ships Ahoy - Saint Michaels, MD
No reviews

Ships Ahoy

house, Oxford
Minutes From Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova - Saint Michaels, MD
9.6 10 reviews

Minutes From Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova

apartment, Tilghman Island
Sunset Landing In Easton, Md. - Saint Michaels, MD
10 1 review

Sunset Landing In Easton, Md.

apartment, Easton

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.

Sail Cove | An Esvr Property - Saint Michaels, MD
No reviews

Sail Cove | An Esvr Property

apartment, Grasonville
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk To Bar & Restaurant! - Saint Michaels, MD
10 131 reviews

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk To Bar & Restaurant!

apartment, Stevensville
Sail Cove | An Esvr Property - Saint Michaels, MD
No reviews

Sail Cove | An Esvr Property

apartment, Grasonville
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