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Saint Michaels, MD apartments
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28 Apartments or condos in Saint Michaels, MD

Best Family-Friendly Vacation Apartments in Saint Michaels, MD

Traveling to Saint Michaels, MD with kids? These family vacation apartments offer easy beach access and plenty of room to spread out.

Charming Apt. In St. Michaels - Saint Michaels, MD
9.9 91 reviews
Saint Michaels, MD
08/24 – 08/28
$321/nighttotal: $1284 (4 )

Charming Apt. In St. Michaels

1 2
apartment , Easton
This Easton studio apartment, located in St. Michael's historic district on Talbot Street, is steps from the Miles River and near shops, museums, and restaurants.
The renovated 1850s McMillian House unit offers a queen bed upstairs, a full-size sofa bed downstairs, a full bathroom upstairs, a half-bath downstairs, a kitchenette with refrigerator, microwave, and Keurig, plus free WiFi, YouTube TV, and parking for two cars, accommodating up to four guests.
Cozy, Family-friendly Log Cabin-st. Michaels - Saint Michaels, MD
10 13 reviews
Saint Michaels, MD
08/24 – 08/28
$675/nighttotal: $2700 (4 )

Cozy, Family-friendly Log Cabin-st. Michaels

1 2
apartment , Oxford
This Talbot County, Maryland log cabin retreat is located three miles from the historic town of St. Michaels.
This four-bedroom, two-bathroom house comfortably sleeps eight guests and offers a fully equipped kitchen, air conditioning, internet access, pet-friendly accommodations, parking, and opportunities for outdoor activities such as s'mores roasting.
Tilghman | Pool | Private Dock | Pet Friendly - Saint Michaels, MD
9.4 15 reviews
Saint Michaels, MD
06/25 – 07/01
$950/nighttotal: $5700 (6 )

Tilghman | Pool | Private Dock | Pet Friendly

3 4
apartment , Tilghman Island
This waterfront vacation rental is located just a short walk from the Tilghman Watermen’s Museum and within a 25-mile radius of other notable attractions like Chesapeake Bay Maritime Museum and St. Michaels Museum. The property enjoys excellent ratings for user experience, location, and cleanliness.
The house has three bedrooms and three bathrooms, spanning 2060 square feet, and comfortably accommodates six guests. Enjoy stunning waterfront views, relax in the private pool and spa tub, and take advantage of the fully equipped kitchen, garden, barbecue grills, and patio with free Wi-Fi.
Stay By The Chesapeake On Kent Island This Mother Day! < 20 Mi From Annapolis. - Saint Michaels, MD
10 41 reviews
Saint Michaels, MD
08/08 – 08/10
$1261/nighttotal: $2522 (2 )

Stay By The Chesapeake On Kent Island This Mother Day! < 20 Mi From Annapolis.

5 6
apartment , Stevensville
This family-friendly vacation home is conveniently located near the sea in Stevensville, within a 15-kilometer radius of Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
This 5-bedroom, 2-bathroom house spans 2,190 square feet and can accommodate up to 14 guests. It comes equipped with a range of amenities, including a fitness center, spa, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable vacation experience.

Our Favorite Vacation Apartments with Swimming Pool in Saint Michaels, MD

Dip in whenever you like, as these vacation apartments near the water in Saint Michaels, MD come with a convenient swimming pool on-site.

Fairview Estate | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
06/25 – 07/01
$3593/nighttotal: $21558 (6 )

Fairview Estate | An Esvr Property

6 4
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.
Waterfront - 3 Luxury Bdrms W/ Outside Pool & Spa - Saint Michaels, MD
9.7 15 reviews
Saint Michaels, MD
06/28 – 07/01
$1156/nighttotal: $3468 (3 )

Waterfront - 3 Luxury Bdrms W/ Outside Pool & Spa

1 2
apartment , Tilghman Island
This apartment sits on Tilghman Island, a charming island community with a rich maritime history, offering water views and easy access to fishing, crabbing, and kayaking on the Chesapeake Bay. It has received excellent ratings for user experience, location, and cleanliness.
This comfortable home has three bedrooms and three bathrooms, accommodating up to six guests. Enjoy a family-friendly atmosphere with amenities like a pool, jacuzzi, fitness center, and a spacious family room with a pool table and bar area.
*Waterfront* 5br W/ Pool + Firepit On Kent Island! - Saint Michaels, MD
10 13 reviews
Saint Michaels, MD
06/27 – 06/28
$2701/nightfor 1 night

*Waterfront* 5br W/ Pool + Firepit On Kent Island!

1 2
apartment , Stevensville
This Stevensville condo offers a private waterfront setting on Kent Island with open water views, just a short walk to the community Bay beach and close to local wineries, seafood restaurants, and marinas.
This spacious 3-bathroom rental accommodates up to 12 guests and features a resort-style private pool, a playroom, a pirate bunk room, a playground, a fully stocked kitchen, and an outdoor firepit on the water.
Minutes From Downtown Easton And St. Michaels | Pool | 1st Floor Bedroom | Pet F - Saint Michaels, MD
9.0 4 reviews
Saint Michaels, MD
06/25 – 07/01
$1144/nighttotal: $6864 (6 )

Minutes From Downtown Easton And St. Michaels | Pool | 1st Floor Bedroom | Pet F

5 4
apartment , Easton
Quailsar Farm is a beautiful vacation rental located in Easton, Maryland, within easy reach of local landmarks like the Avalon Theatre and The Third Haven Friends Meeting House. The farm offers a peaceful escape from the city, with a relaxing rural setting. This highly-rated property has received excellent reviews from previous guests.
The 5-bedroom, 4-bathroom home spans 5070 square feet and can comfortably accommodate up to 10 guests. The farm offers a range of amenities, including a gourmet kitchen, a swimming pool, and a spacious backyard perfect for outdoor activities.

Frequently Asked Questions about apartment rentals in Saint Michaels, MD

Destinations nearby

Best Saint Michaels, MD apartment rentals with air conditioning

Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD
10 6 reviews
Saint Michaels, MD
08/08 – 08/10
$820/nighttotal: $1640 (2 )

Downtown Oxford | Outdoor Dining | Character Filled

3 6
apartment , Oxford
This Oxford vacation rental is located in a peaceful neighborhood, just a short walk from the waterfront restaurants, ice cream shops, and parks. It's also a quick drive to St. Michaels and Tilghman Island, making it a great base for exploring the Eastern Shore. This 3-bedroom, 2-bathroom apartment offers 1510 square feet of space and can comfortably accommodate up to 6 guests. The home features a well-equipped kitchen, a large deck with a picnic table, and a propane grill, perfect for enjoying meals and gatherings. It's also close to walking, biking, kayaking, and sailing opportunities.
Minutes To All Tilghman Island Wedding Venues - Saint Michaels, MD
9.4 13 reviews
Saint Michaels, MD
07/01 – 07/05
$411/nighttotal: $1644 (4 )

Minutes To All Tilghman Island Wedding Venues

3 2
apartment , Tilghman Island
This Tilghman Island vacation rental, located in Talbot County, Maryland, is minutes from St. Michaels and offers easy access to restaurants and shops by foot or bike.
The three-bedroom, two-bathroom house sleeps six guests and features a well-equipped kitchen, outdoor fire pit and patio, front porch, back deck, and an espresso machine; nearby attractions include waterfront dining and a Tiki bar.
Downtown St. Michaels | Bikes | Kayaks | Private Pier - Saint Michaels, MD
10 43 reviews
Saint Michaels, MD
06/28 – 07/01
$1042/nighttotal: $3126 (3 )

Downtown St. Michaels | Bikes | Kayaks | Private Pier

3 2
apartment , Easton
This waterfront vacation home is situated within a 15-minute walk of St. Michaels Winery and St. Michaels Museum, and 1.2 miles from Chesapeake Bay Maritime Museum. It has excellent user, location, and cleanliness ratings.
The house has 3 bedrooms, a floor area of 2190 square feet, and a guest capacity of 6. It features a fully equipped kitchen, a patio, a fireplace, a spa, a tennis court, barbecue grills, and parking.
Dr. Miller House. Best Location-in The Heart Town - Saint Michaels, MD
9.8 211 reviews
Saint Michaels, MD
08/24 – 08/28
$343/nighttotal: $1372 (4 )

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

2 2
apartment , Easton
This newly renovated apartment is located in a charming district of Easton, just three blocks from the waterfront and within walking distance of shops, restaurants, a winery, a brewery, and coffee shops. This Easton rental has received excellent ratings for location, cleanliness, and overall user experience.
The duplex offers two bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment features a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, parking, and internet access.

Traveler-Approved Pet-Friendly Apartments in Saint Michaels, MD

Bringing your dog to Saint Michaels, MD? Every apartment here is pet-ready with dog-friendly beaches and washing facilities.

Bay Escape - Saint Michaels, MD
Saint Michaels, MD
08/08 – 08/10
$513/nighttotal: $1026 (2 )

Bay Escape

3 6
apartment , Stevensville
This Stevensville apartment offers a peaceful retreat in a quiet district, providing a tranquil atmosphere away from the city center.
This family-friendly residence accommodates up to 8 guests with 2 bathrooms, a full kitchen including a fridge, air conditioning, and a garden, and allows pets.
The Getaway - Saint Michaels, MD
10 20 reviews
Saint Michaels, MD
06/25 – 07/01
$378/nighttotal: $2268 (6 )

The Getaway

1 4
apartment , Tilghman Island
This apartment on Tilghman Island is a short walk from the well-known "Two if by Sea" restaurant and the General Store, offering convenient access to local amenities and dining.
This spacious rental accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, a garden, and parking, making it ideal for barbecues and exploring the island by bike.
Bankors Aweigh | An Esvr Property - Saint Michaels, MD
9.5 11 reviews
Saint Michaels, MD
08/24 – 08/28
$1054/nighttotal: $4216 (4 )

Bankors Aweigh | An Esvr Property

1 2
apartment , Tilghman Island
This waterfront home on Tilghman Island, Talbot County, offers easy access to local shops and restaurants.
The 4-bedroom, 1.5-bathroom house sleeps 8, features a full kitchen, in-ground pool, jacuzzi, and direct Chesapeake Bay access.
Tilghman | Fenced Yard | Pet Friendly | Charming - Saint Michaels, MD
9.3 6 reviews
Saint Michaels, MD
06/25 – 07/01
$537/nighttotal: $3222 (6 )

Tilghman | Fenced Yard | Pet Friendly | Charming

3 4
apartment , Tilghman Island
This Tilghman Island rental is conveniently located on the island, offering waterfront views and easy access to local restaurants and shops.
This 1470-square-foot, three-bedroom, two-bathroom house sleeps six, features a well-equipped kitchen with a dishwasher and microwave, and includes linens, towels, and a starter supply pack.
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