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Saint Michaels, MD vacation rentals
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Best Vacation rentals and Airbnb offers in Saint Michaels, MD

Best Saint Michaels, MD vacation rentals with a balcony

Beautiful 3 Bedroom Retreat Walking Distance To Downtown St. Michaels - Saint Michaels, MD
10 12 reviews

Beautiful 3 Bedroom Retreat Walking Distance To Downtown St. Michaels

apartment, Easton
This Easton apartment rental is conveniently located a 6-minute walk from St. Michaels Winery and a 7-minute walk from the St. Michaels Museum, offering easy access to Talbot County attractions.
This three-bedroom, one-bathroom unit sleeps six guests and features a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, and a dedicated workspace; nearby activities include Windon Distilling and the Chesapeake Bay Maritime Museum.
St. Michaels Escape | Pool, Hot Tub & Fire Pit - Saint Michaels, MD
10 9 reviews

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

apartment, Tilghman Island
This private waterfront oasis, known as The Kipsy, is located on Porters Creek in Talbot County, offering direct access and creek views just minutes from St. Michaels.
This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a private pool, hot tub, fire pit, and dock, ideal for fishing or kayaking, with a fully equipped kitchen and spacious living areas designed for entertaining.
The Suite At Mostly Porches - Saint Michaels, MD
10 81 reviews

The Suite At Mostly Porches

house, Easton
This charming apartment in St. Michaels is just steps from the Auto Museum, Maritime Museum, YMCA, and a variety of restaurants. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom apartment is ideal for two guests.
The 480-square-foot apartment features a kitchen with a fridge, freezer, and microwave, as well as air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking. Laundry facilities are available upon request for longer-term renters.
Cozy 2-bedroom Cottage On Tilghman Island  Near Restaurants & Water Activities - Saint Michaels, MD
10 13 reviews

Cozy 2-bedroom Cottage On Tilghman Island Near Restaurants & Water Activities

apartment, Tilghman Island
This two-bedroom cottage is located on Tilghman Island, Maryland, within walking distance of the Tilghman Island Country Store and a short drive from Knapp's Narrows Marina & Inn.
The 2-bathroom vacation home sleeps four and features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a garden, parking, and internet access; nearby attractions include the Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum.

Browse Family-Friendly Vacation Rentals in Saint Michaels, MD

Find the perfect family vacation rental or Airbnb in Saint Michaels, MD with plenty of room to spread out near local beaches.

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 home sits on a 3-acre property near St. Michaels and Easton, a nationally-recognized town. Guests rave about its excellent location, cleanliness, and overall experience.
This charming apartment sleeps 6 guests and features a fully equipped kitchen, a cozy living room with a fireplace, and a large deck with a screened porch. Guests can enjoy kayaking, biking, and grilling, plus the property includes a fire pit, yard games, and a private pier with a tidal cove.
True St. Michaels 6 Acre Waterfront W/heated Pool - Saint Michaels, MD
10 197 reviews

True St. Michaels 6 Acre Waterfront W/heated Pool

cabin, Easton
This charming cabin is situated on a 6-acre waterfront lot just outside of Historic Downtown Saint Michaels, a quick 5-10 minute bike ride away. It has received excellent ratings for location, cleanliness, and overall experience from previous guests. The cabin offers spacious accommodation with 3,000 square feet of space and comfortably sleeps up to 8 guests. Enjoy a range of amenities including a private pool, a jacuzzi, a tennis court, and a well-equipped kitchen.
The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground! - Saint Michaels, MD
9.6 5 reviews

The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground!

apartment, Stevensville
This waterfront apartment in Stevensville, Maryland, offers a private retreat on Chews Creek with panoramic water views, located minutes from local wineries, seafood restaurants, and boutique shops.
This 3000-square-foot residence accommodates up to 12 guests with five bedrooms, four bathrooms, and features a private seasonal swimming pool, an outdoor firepit, a well-equipped kitchen, and access to a community beach a 10-minute walk away.
The Little Anchor Cottage, St. Michaels, Md - Saint Michaels, MD
9.9 294 reviews

The Little Anchor Cottage, St. Michaels, Md

apartment, Easton
The Little Anchor cottage is located in the Historic District of St. Michaels, Maryland, just one block from downtown shops and restaurants and a short walk from the waterfront, museums, and parks. It has received excellent ratings for location, cleanliness, and overall user experience.
The charming cottage has two bedrooms and one bathroom and can accommodate up to four guests. The home features a fully equipped kitchen, a screened-in porch, a private garden, and fast Wi-Fi, making it perfect for families or groups looking to explore the area.

Frequently Asked Questions about vacation 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 lots to see! You can visit the Chesapeake Bay Maritime Museum, which has a great collection of historic boats and exhibits. For a scenic view, head to the St. Michaels Museum of Art, perched on the waterfront. If you're looking for something a little different, check out the St. Michaels Winery, which offers tastings and tours. For a day trip, you can also explore the nearby town of Easton, which has a vibrant downtown area with shops and restaurants.
  • What are the best Airbnb and vacation 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 the most popular Airbnb and vacation rentals in Saint Michaels, MD among travelers.

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

    The town is very walkable, but for a longer ride, you can try the scenic 10-mile loop around the Miles River. The trail runs along the water, offering beautiful views of the Chesapeake Bay. If you're looking for a shorter walk, the boardwalk along the harbor is a great option. You can also check out the St. Michaels Walking Trail, which offers a variety of routes through town.
  • What are the most popular Airbnbs in Saint Michaels, MD?

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

    St. Michaels is a great place for water sports. You can rent a kayak or canoe and explore the waterways, or take a boat tour to see the local wildlife. If you're feeling adventurous, you can even try paddleboarding or windsurfing. For land-based activities, there are plenty of hiking and biking trails in the area, as well as several golf courses.
  • What are the best vacation rentals with a pool in Saint Michaels, MD?

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

    St. Michaels is located on the Eastern Shore of Maryland, about an hour and a half drive from Baltimore and about two hours from Washington, D.C. You can also easily reach Annapolis, the state capital, in about an hour. If you're looking for a more relaxed beach town, Ocean City is about a two-hour 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 St. Michaels typically offer a range of amenities, including fully equipped kitchens, comfortable bedrooms, and private bathrooms. Many rentals also have outdoor spaces like patios or balconies, as well as access to laundry facilities. Some rentals may also offer amenities like hot tubs, fireplaces, and private docks.
  • What are the best rentals or Airbnbs with a jacuzzi in Saint Michaels, MD?

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

    The best time to visit St. Michaels is during the shoulder seasons, spring and fall. The weather is mild, and the crowds are smaller. You can enjoy the beautiful scenery and outdoor activities without the heat and humidity of summer. If you're looking for a more festive experience, you can visit during the holiday season, when the town is decorated for Christmas.

Popular destinations

Best Saint Michaels, MD vacation rentals with parking

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 vacation home is located near St. Michaels, within 3 miles of St. Michaels Winery and St. Michaels Museum, and within 6 miles of Chesapeake Bay Maritime Museum and Oxford Museum, offering a peaceful escape from the hustle and bustle of city life. This property has received excellent user ratings, making it a popular choice for travelers.
This 3,000 square foot home features 3 bedrooms and 3 bathrooms, comfortably accommodating up to 6 guests. Enjoy stunning views of the Chesapeake Bay, a private pool, a terrace, a garden, a spa, and family-friendly amenities like a water park and barbecue grills.
The Weekender - Saint Michaels, MD
No reviews

The Weekender

house, Tilghman Island
The Weekender, a house in Mount Pleasant, MD, is conveniently located 16 miles from the Maryland Institute College of Art and 66 miles from Baltimore/Washington International Thurgood Marshall Airport, offering easy access to Tilghman Island and the Eastern Shore.
This one-bathroom home sleeps seven guests and features free Wi-Fi, private parking, a fully equipped kitchen, and is pet-friendly, perfect for a peaceful getaway near Tilghman Island.
Waterfront Family Retreat - Mins From St. Michaels - Saint Michaels, MD
10 4 reviews

Waterfront Family Retreat - Mins From St. Michaels

apartment, Oxford
This 6-bedroom, 4-bathroom residence in Oxford offers a tranquil waterside setting with a private dock for crabbing and fishing, situated a short distance from Oxford's cultural attractions.
This spacious apartment accommodates up to 12 guests and features a chef-ready kitchen, an outdoor entertainment area with a fire pit and TV, a fenced yard with a play area, a pool, a spa, and spectacular sunset views.
Vintage Pet-friendly Cottage | Tilghman Island - Saint Michaels, MD
No reviews

Vintage Pet-friendly Cottage | Tilghman Island

apartment, Tilghman Island
This pet-friendly cottage is located in the waterfront community of Tilghman Island, Maryland, offering proximity to local marinas, waterfront restaurants, and a short drive to historic St. Michaels.
This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features air conditioning, internet, a kitchen with a fridge, and parking, curated by Flaneur for intentional comfort.

Choose the Right Vacation Rentals with a Pool in Saint Michaels, MD

Complement your time by the water with a dip in the pool at these Saint Michaels, MD vacation rentals with on-site swimming facilities.

Fairview Estate | An Esvr Property - Saint Michaels, MD
No reviews

Fairview Estate | An Esvr Property

apartment, Easton
Fairview Estate is a historic property located in Talbot County, a short drive from the charming town of Easton on Maryland's Eastern Shore. The estate offers a peaceful setting, perfect for a relaxing getaway.
This 6-bedroom, 4-bathroom home can comfortably accommodate up to 12 guests. Fairview Estate provides a fully equipped kitchen, a swimming pool, a fitness center, and a garden, offering a variety of amenities for a comfortable and enjoyable stay.
Pool House Paradise - Saint Michaels, MD
10 2 reviews

Pool House Paradise

house, Grasonville
This secluded pool house apartment is located in the Prospect Bay waterfront and golf community on Maryland's Eastern Shore, offering bay views and convenient access to local recreation.
This 1-bedroom, 1-bathroom apartment accommodates 2 guests and features a private fenced backyard with a pool, hot tub, and fire pit, along with access to community amenities including golf and tennis courts.
Tilghman Island Inn - Saint Michaels, MD
No reviews

Tilghman Island Inn

house, Tilghman Island
This waterfront boutique inn on Tilghman Island, Maryland's Eastern Shore, offers exclusive buyouts with sweeping Chesapeake Bay views and private docks.
This inn accommodates 16 guests across 20 private rooms, featuring internet, air conditioning, a swimming pool, and 22 bathrooms, ideal for group events and offering a private, secluded retreat experience.
Waterfront Getaway W/ Pool + Beaches+ Hot Tub +Bbq - Saint Michaels, MD
9.9 61 reviews

Waterfront Getaway W/ Pool + Beaches+ Hot Tub +Bbq

house, Grasonville
This Grasonville waterfront apartment offers convenient access to private beaches with fire pits, boat launches, and shared amenities including a heated pool, pier, and volleyball court.
The one-bedroom, one-bathroom unit sleeps three guests and features a microwave, air conditioning, and access to kayaks and paddleboards; evening boat rides, fishing, and crabbing trips are available.

Find the Best Seaside Vacation Rentals in Saint Michaels, MD

Discover beautiful beach towns with these seaside vacation rentals in Saint Michaels, MD, perfect for relaxing near the coast and exploring the shore.

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Saint Michaels, MD
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
Herons Roost - Saint Michaels, MD
No reviews

Herons Roost

house, Tilghman Island
Ferry View | An Esvr Property - Saint Michaels, MD
10 3 reviews

Ferry View | An Esvr Property

apartment, Oxford
Waterfront, Dog Friendly, St Michaels Home - Saint Michaels, MD
9.9 160 reviews

Waterfront, Dog Friendly, St Michaels Home

apartment, Tilghman Island

Traveler-Approved Luxury Vacation Rentals in Saint Michaels, MD

These high-end vacation rentals in Saint Michaels, MD offer luxury living and unmatched quality near the shore.

Minutes From Downtown St. Michaels | Guest House | Pool | Private Dock - Saint Michaels, MD
9.0 6 reviews

Minutes From Downtown St. Michaels | Guest House | Pool | Private Dock

apartment, Oxford

Explore Vacation Rentals with Saunas in Saint Michaels, MD

Maximize your recovery with an on-site sauna, a standard feature at these premier Saint Michaels, MD vacation rentals.

St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly - Saint Michaels, MD
9.8 43 reviews

St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly

apartment, Tilghman Island
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