Places to stay in Saint Michaels, MD

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Saint Michaels, MD place to stay
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46 Best places to stay in Saint Michaels, MD

Best Saint Michaels, MD lodgings with a pool

Among the 46 accommodations in Saint Michaels, MD, here are the 4 best ones with a pool

Bayview 2.0 | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
19/07 – 22/07
SG$4112/nighttotal: SG$12336 (3 )

Bayview 2.0 | An Esvr Property

6 11
apartment , Tilghman Island
This waterfront estate in McDaniel, located on Tilghman Island, boasts expansive views of the Eastern Bay, approximately 16 kilometres from St. Michaels and 35 kilometres from Easton.
This six-bedroom holiday home accommodates up to 12 guests, offering a heated saltwater pool, hot tub, private dock, and crabbing gear, with luxury rental benefits including concierge services and local guides.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.6 20 reviews
Saint Michaels, MD
24/06 – 28/06
SG$387/nighttotal: SG$1548 (4 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 3
apartment , Trappe
This four-bedroom holiday home is situated in a peaceful neighbourhood in Trappe, Maryland, just seven miles from Oxford Beach and a short drive from Cambridge and St. Michaels. The property offers easy access to the beautiful Chesapeake Bay and its surrounding historic towns.
This spacious property can comfortably accommodate up to eight guests, offering a private outdoor pool, a large garden with a treehouse, a gazebo, a fire pit and a deck with umbrellas. The home also features a fully equipped kitchen, a private office with two workstations, a washer and dryer, and central air conditioning and heating.
Relax- Eastern Shore Creek Home - 6 Guests - Saint Michaels, MD
10 6 reviews
Saint Michaels, MD
08/08 – 10/08
SG$972/nighttotal: SG$1944 (2 )

Relax- Eastern Shore Creek Home - 6 Guests

3 6
apartment , Grasonville
This Grasonville property, situated within the Prospect Bay Country Club, is located 24 kilometres east of the Chesapeake Bay Bridge, offering tranquil creek views.
This three-bedroom, four-bathroom holiday home boasts over 300 square metres of space, sleeping up to eight guests and featuring a Jacuzzi, microwave, dishwasher, and parking; nearby attractions include the St. Michaels Museum and Avalon Theatre.
Fairview Estate - Saint Michaels, MD
Saint Michaels, MD
25/06 – 01/07
SG$4511/nighttotal: SG$27066 (6 )

Fairview Estate

1 4
house , Easton
Fairview Estate, a large house in Saint Michaels, Maryland, is situated 14.2 km from the Academy of the Arts and 43.5 km from the Chesapeake Exploration Center, offering easy access to the Chesapeake Bay.
This six-bedroom, six-bathroom property boasts 557 square metres of floor space, accommodating up to 23 guests and featuring a private pool, free Wi-Fi, parking, and a fully equipped kitchen; pets are welcome.

Best family friendly Saint Michaels, MD lodging

Among the 46 accommodations in Saint Michaels, MD, here are the 4 best for families

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Golf Cours - Saint Michaels, MD
10 2 reviews
Saint Michaels, MD
25/06 – 01/07
SG$4455/nighttotal: SG$26730 (6 )

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

6 4
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.
Bay Escape - Saint Michaels, MD
Saint Michaels, MD
08/08 – 10/08
SG$659/nighttotal: SG$1318 (2 )

Bay Escape

3 6
apartment , Stevensville
This family-friendly flat in Stevensville offers a peaceful retreat in a quiet district, providing convenient access to local attractions without the noise of central areas.
This spacious accommodation for up to 8 guests features air conditioning, a garden, and a kitchen equipped with a fridge, making it ideal for a comfortable and tranquil family stay.
Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues - Saint Michaels, MD
10 129 reviews
Saint Michaels, MD
31/07 – 06/08
SG$1394/nighttotal: SG$8364 (6 )

Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues

1 11
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.
Modern Island Escape By The Bay - Saint Michaels, MD
9.9 81 reviews
Saint Michaels, MD
31/07 – 03/08
SG$853/nighttotal: SG$2559 (3 )

Modern Island Escape By The Bay

5 10
apartment , Stevensville
This Stevensville island property, conveniently located near the Bay Bridge for easy access to Annapolis and Washington D.C., offers a central location to various wedding venues and restaurants.
Sleeping up to eight guests, this three-bedroom, two-bathroom holiday home boasts a 2023 renovation with an island-themed design, a large kitchen island, spacious back deck with a fire pit, and includes air conditioning, Wi-Fi, parking and pet-friendly options.

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.

Destinations nearby

Best Saint Michaels, MD accommodations with a balcony

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
Saint Michaels, MD
24/06 – 28/06
SG$421/nighttotal: SG$1684 (4 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 3
house , Trappe
This spacious holiday home is located in Trappe, just 5.5 miles from the Academy of the Arts and 25 miles from Federalsburg Marina, offering a tranquil escape in a charming town with a rich history. The property spans 204 square metres and comfortably accommodates up to 8 guests, providing ample space for families or groups.
The house is fully equipped with modern amenities including a kitchen with a fridge, microwave oven, and dishwasher, a private outdoor pool and gazebo, air conditioning, and free Wi-Fi. Guests can also enjoy a dedicated outdoor dining area, a washing machine, and parking.
Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 1 review
Saint Michaels, MD
27/06 – 04/07
SG$449/nighttotal: SG$3143 (7 )

Relax On Kent Island In 3 Bedroom Home W/waterview

4 2
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.
Charming 3-bedroom  In Village Of Claiborne \Nbook 3 Nights Get 4th Free Strn26-6 - Saint Michaels, MD
10 1 review
Saint Michaels, MD
01/07 – 05/07
SG$569/nighttotal: SG$2276 (4 )

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

3 2
apartment , Tilghman Island
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.
Dollhouse In Central Historic St Michaels - Saint Michaels, MD
9.6 119 reviews
Saint Michaels, MD
24/06 – 28/06
SG$467/nighttotal: SG$1868 (4 )

Dollhouse In Central Historic St Michaels

2 3
apartment , Easton
This charming house is located in St. Michaels, a picturesque town on Maryland's Eastern Shore, just 1 kilometre from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms, accommodating up to four guests, and features a fully equipped kitchen, two bathrooms, a washing machine, and a Smart TV. Guests can enjoy a spa tub, garden, barbecue grills, and a terrace, making it ideal for relaxation and outdoor dining.

Best Saint Michaels, MD accommodations with a kitchen

Chesapeake Bay Overlook Home - Saint Michaels, MD
10 1 review
Saint Michaels, MD
31/07 – 06/08
SG$1225/nighttotal: SG$7350 (6 )

Chesapeake Bay Overlook Home

1 11
apartment , Shady Side
This Shady Side holiday home is located near the Chesapeake Bay and marina, within walking distance of the beach.
Sleeping up to 12 guests, this six-bedroom, three-bathroom property boasts a fully equipped kitchen, laundry facilities, a large entertainment room with a pool table and bar, and stunning Chesapeake Bay views from three expansive decks; nearby attractions include fresh seafood at the marina.
Off The Chart Stays - Saint Michaels, MD
10 29 reviews
Saint Michaels, MD
01/07 – 05/07
SG$1380/nighttotal: SG$5520 (4 )

Off The Chart Stays

1 2
apartment , Stevensville
This charming cottage is situated on Kent Island, Maryland, just a short drive from Annapolis, Washington D.C., and Baltimore, offering a peaceful retreat near the Chesapeake Bay. The two-bedroom cottage comfortably sleeps six guests, making it ideal for families or groups of friends. The cottage features a well-equipped kitchen, a private sauna, a large screened-in porch, and a fire pit, allowing guests to relax and enjoy the beautiful surroundings.
It's A Shore Thing Located In Beautiful Easton, Md. Close To Md & De Beaches. - Saint Michaels, MD
10 4 reviews
Saint Michaels, MD
01/07 – 05/07
SG$416/nighttotal: SG$1664 (4 )

It's A Shore Thing Located In Beautiful Easton, Md. Close To Md & De Beaches.

2 2
apartment , Easton
This two-bedroom apartment in Easton is situated a mere 4-minute drive from the Avalon Theatre and Academy of the Arts, offering excellent access to local attractions and outdoor pursuits such as birdwatching and cycling.
This 104 square meter property accommodates up to four guests, featuring a fully equipped kitchen with a microwave oven, air conditioning, Wi-Fi, and on-site parking, with the added convenience of an in-unit washer and dryer.
Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD
10 6 reviews
Saint Michaels, MD
07/08 – 09/08
SG$1034/nighttotal: SG$2068 (2 )

Downtown Oxford | Outdoor Dining | Character Filled

3 2
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.
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