Search accommodations in Saint Michaels, MD

46 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Saint Michaels, MD place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

46 Lodgings in Saint Michaels, MD

Best Saint Michaels, MD lodging with a pool

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

Relax- Eastern Shore Creek Home - 6 Guests - Saint Michaels, MD
10 6 reviews
Saint Michaels, MD
07/08 – 09/08
₹72145/nighttotal: ₹144290 (2 )

Relax- Eastern Shore Creek Home - 6 Guests

3 2
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.
*Waterfront* 5br W/ Pool + Firepit On Kent Island! - Saint Michaels, MD
10 13 reviews
Saint Michaels, MD
27/06 – 28/06
₹257832/nightfor 1 night

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

1 2
apartment , Stevensville
This private waterfront estate on Kent Island, Stevensville, offers 1.5 acres of land with direct access to a private community beach and panoramic water views, situated conveniently near marinas, wineries, seafood restaurants, golf courses, and hiking trails.
This five-bedroom holiday home accommodates up to 12 guests with a gated private pool, lounge areas, a firepit, two coffee bars, a gourmet kitchen, and a dedicated play area, alongside indoor and outdoor games, making it ideal for family stays and entertaining.
Skipjack House | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
27/06 – 04/07
₹52093/nighttotal: ₹364651 (7 )

Skipjack House | An Esvr Property

3 4
apartment , Tilghman Island
Skipjack House, a single-level holiday home on Tilghman Island, is located in St. Michaels, offering a comfortable base for exploring the Eastern Shore.
This property sleeps six guests with three bedrooms, two bathrooms, and includes a fully equipped kitchen, air conditioning, and access to a swimming pool, with linens and towels provided.
Tilghman Island Inn - Saint Michaels, MD
Saint Michaels, MD
25/06 – 01/07
₹523425/nighttotal: ₹3140550 (6 )

Tilghman Island Inn

20 4
house , Tilghman Island
This exclusive buyout of a boutique waterfront inn on Tilghman Island offers 20 private guest rooms with sweeping Chesapeake Bay views and private docks, ideal for group gatherings.
The inn accommodates up to 16 guests with 22 bathrooms, featuring internet, air conditioning, and a swimming pool, providing a private and comfortable setting for family reunions, wedding weekends, and corporate retreats.

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 St. Michaels | Character Filled - Saint Michaels, MD
Saint Michaels, MD
28/06 – 01/07
₹56560/nighttotal: ₹169680 (3 )

Minutes From Downtown St. Michaels | Character Filled

2 2
apartment , Tilghman Island
This two-bedroom holiday home in Bozman, a five-minute (8 km) drive from St. Michaels, offers easy access to the town's waterfront restaurants and shops.
The property features a spacious open-plan layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, patio, yard games, and bikes, plus air conditioning and Wi-Fi.
Skipjack House | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
27/06 – 04/07
₹71004/nighttotal: ₹497028 (7 )

Skipjack House | An Esvr Property

3 2
apartment , Tilghman Island
This 3-bedroom, 2-bathroom holiday home in McDaniel, 1.8 kilometres from St. Michaels Museum and Avalon Theatre, offers a family-friendly stay on Tilghman Island with convenient access to local shops and galleries.
This property accommodates up to six guests and features a private deck with a propane grill, a fenced swimming pool open from May 15 to October 15, complimentary Wi-Fi, air conditioning, and bikes for exploring the area.
The Weekender | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
28/06 – 01/07
₹58866/nighttotal: ₹176598 (3 )

The Weekender | An Esvr Property

2 2
apartment , Tilghman Island
This two-bedroom farmhouse, situated minutes from St. Michaels town centre, offers easy access to its shops and restaurants, lying approximately a few kilometres from Tilghman Island.
The property provides 4 guests with a fully equipped kitchen, including a fridge, microwave, and dishwasher, two bathrooms and a tranquil patio overlooking manicured gardens; linens and towels are included.
Off The Chart Stays - Saint Michaels, MD
10 31 reviews
Saint Michaels, MD
01/07 – 05/07
₹102474/nighttotal: ₹409896 (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.

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 outdoor activities. You can go kayaking or paddleboarding on the Miles River, or take a boat tour to see the local wildlife. There are also plenty of walking and cycling trails in the area, including the scenic Chesapeake Bay Trail.
  • When is the ideal time to plan a trip to Saint Michaels, MD?

    Spring and autumn are the best times to visit Saint Michaels, when the weather is mild and the crowds are smaller. You can enjoy the beautiful scenery without the summer heat and humidity. If you're looking for a more lively atmosphere, you could visit in the summer, but be prepared for larger crowds and higher prices.
  • What are the best walking or cycling routes in Saint Michaels, MD?

    For a scenic walk, try the boardwalk along the Miles River. It's a lovely spot to enjoy the views and watch the boats go by. If you're looking for a longer ride, the Chesapeake Bay Trail is a great option, with over 300km of paved trails that wind through the countryside.
  • What nearby towns or cities can be explored from Saint Michaels, MD?

    If you're looking to explore the surrounding area, Easton is a charming town about 20 minutes away. You can also visit Annapolis, the state capital, which is about an hour's drive away. For a day trip, you could even head to Ocean City, a popular beach resort on the Atlantic coast, about 1.5 hours away.
  • What amenities can travelers expect from accommodations in Saint Michaels, MD?

    Saint Michaels offers a range of accommodation options, from charming bed and breakfasts to luxury hotels. Many accommodations have amenities like swimming pools, restaurants, and boat docks. You can also find plenty of vacation rentals, which are a great option for families or groups.

Destinations nearby

Best Saint Michaels, MD accommodations with a balcony

Downtown Flat  Walk To Dining & Shops  Sleeps 4 - Saint Michaels, MD
10 1 review
Saint Michaels, MD
24/08 – 28/08
₹48821/nighttotal: ₹195284 (4 )

Downtown Flat Walk To Dining & Shops Sleeps 4

1 2
apartment , Easton
This St. Michaels flat is located in the downtown district, a short walk from the waterfront, dining, and shopping areas.
This 76 square meter flat accommodates up to 4 guests, featuring 1 bedroom, 2 bathrooms, a fully stocked kitchen with a coffee bar, a gas fireplace, a king-sized bedroom with a Smart TV, a spa-like ensuite bathroom, high-speed WiFi, an in-unit washer and dryer, and designated parking for two vehicles.
Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
10 4 reviews
Saint Michaels, MD
28/06 – 01/07
₹75556/nighttotal: ₹226668 (3 )

Downtown St. Michaels | Porch + Pet-friendly

3 2
apartment , Easton
This apartment in St. Michaels is situated a short walk from St. Michaels Marina and Higgins Yacht Yard and Marina, placing guests within 500 metres of the waterfront.
This three-bedroom accommodation for six guests offers a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and on-site parking, with Wi-Fi and a washer/dryer provided for convenience.
Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 1 review
Saint Michaels, MD
27/06 – 28/06
₹65202/nightfor 1 night

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.
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 – 10/08
₹120327/nighttotal: ₹240654 (2 )

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

5 6
apartment , Stevensville
This family-friendly house is situated near the sea in Stevensville, just a short drive from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has consistently received excellent ratings from previous guests, making it a popular choice for families and groups visiting the area.
The property spans 203 square metres and comfortably accommodates up to 14 guests in its five bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fitness centre, spa tub, garden, and tennis court, providing plenty of opportunities for relaxation and recreation.

Best Saint Michaels, MD accommodations with a kitchen

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
₹330843/nighttotal: ₹1985058 (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.
Easton's Urban Oasis - Saint Michaels, MD
10 1 review
Saint Michaels, MD
01/07 – 05/07
₹42121/nighttotal: ₹168484 (4 )

Easton's Urban Oasis

1 2
house , Easton
This Easton apartment is centrally located, within walking distance of Four Dogs Brewing, Tiger Lily, and the Tidewater Inn, and a short drive (approximately 16-32 km) from Oxford and St Michaels.
This three-bedroom, one-bathroom flat sleeps six, offering a fully equipped kitchen, air conditioning, parking, and internet access; guests can enjoy easy access to Easton's shopping centre and a family-friendly atmosphere.
The Farm At Cedar Cove | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
25/06 – 01/07
₹63029/nighttotal: ₹378174 (6 )

The Farm At Cedar Cove | An Esvr Property

3 4
apartment , Oxford
This waterfront property in Royal Oak offers 18 acres of secluded farmland with over 1,000 feet of private shoreline, situated 15 minutes from St. Michaels and Easton.
This renovated 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, garden, parking, and internet, with the Oxford-Bellevue Ferry and cycling routes nearby.
Downtown Retreat With Bikes, Fire Pit & Kayaks - Saint Michaels, MD
10 23 reviews
Saint Michaels, MD
28/06 – 01/07
₹55721/nighttotal: ₹167163 (3 )

Downtown Retreat With Bikes, Fire Pit & Kayaks

2 2
apartment , Easton
This two-bedroom flat in St. Michaels is located a few minutes' drive from the town centre, offering convenient access to shops, restaurants, breweries, and wineries.
This pet-friendly apartment accommodates four guests and features a modern open-plan living space, two en-suite bedrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, complimentary bikes, two kayaks, a fire pit, and a BBQ grill.
©2026 cozycozy.com