Places to stay in Saint Michaels, MD

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

Best Saint Michaels, MD lodgings with a pool

Among the 76 accommodations in Saint Michaels, MD, here are the 4 best ones with a pool

Minutes From Downtown St. Michaels | Pool | Kayaks | 350 Ft Of Shoreline | Luxur - Saint Michaels, MD
No reviews

Minutes From Downtown St. Michaels | Pool | Kayaks | 350 Ft Of Shoreline | Luxur

apartment, Tilghman Island
This six-bedroom, six-bathroom waterfront apartment is located in St. Michaels, a short distance from the Chesapeake Bay Maritime Museum and St. Michaels Museum, offering easy access to local attractions and activities. The 387 square metre property boasts a spacious open floor plan, a chef-inspired kitchen with dual ovens and a wine fridge, two master suites with ensuite bathrooms, a resort-style backyard with a swimming pool, and a screened porch, perfect for large families or groups of up to 12 guests.
Bayside The Point - Saint Michaels, MD
No reviews

Bayside The Point

house, Oxford
This spacious six-bedroom property, perfect for large groups, is situated near Royal Oak, Maryland, approximately 13.7 kilometres from the Academy of the Arts and 95 kilometres from Baltimore-Washington International Airport; note that this property is not located in Oxford.
The 224-square-metre house boasts four bathrooms, a private swimming pool, jacuzzi, free Wi-Fi, and parking, comfortably accommodating up to 23 guests.
The Eagles Nest - Saint Michaels, MD
No reviews

The Eagles Nest

house, Grasonville
The Eagles Nest property in Grasonville, Maryland, is situated approximately 27 kilometres from Sandy Point State Park, 39 kilometres from the United States Naval Academy, and 40 kilometres from Annapolis.
This five-bedroom house boasts a private pool, four bathrooms, free Wi-Fi, and parking, comfortably accommodating up to 27 guests and offering self-catering facilities in its fully equipped kitchen.
Summer Retreat  Pool, Hot Tub & Outdoor Oasis - Saint Michaels, MD
9.6 17 reviews

Summer Retreat Pool, Hot Tub & Outdoor Oasis

apartment, Tilghman Island
This freshly remodelled 2024 waterfront farmhouse in Talbot County, Maryland, is situated approximately 16km from Saint Michaels, offering easy access to its shops and restaurants.
This three-bedroom, three-bathroom property sleeps six guests and boasts a private pool, hot tub, extensive grounds, a fully equipped kitchen including a dishwasher, and complimentary internet access; pets are welcome (surcharge applies).

Best family friendly Saint Michaels, MD lodging

Among the 76 accommodations in Saint Michaels, MD, here are the 4 best for families

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk To Bar & Restaurant! - Saint Michaels, MD
10 130 reviews

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

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.
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 5 to 15 minute walk from waterfront dining, the Chesapeake Bay Maritime Museum, Muskrat Park, and Hollis Park. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The charming two-bedroom property can accommodate up to four guests and features a fully equipped kitchen, a spacious screened porch, a garden, and high-speed Wi-Fi. Guests can enjoy dedicated workspaces, air conditioning, and the convenience of being pet-friendly and family-friendly.
Minutes From Downtown St. Michaels | Pool | Dock - Saint Michaels, MD
10 2 reviews

Minutes From Downtown St. Michaels | Pool | Dock

apartment, Tilghman Island
This stunning cedar Lindal home, situated near St. Michaels on Tilghman Island's Eastern Shore, offers breathtaking Broad Creek waterfront views and is a short drive from St. Michaels Museum and Avalon Theatre.
Sleeping up to six guests, this three-bedroom, three-bathroom property boasts a chef-inspired kitchen, private heated pool (seasonal, 15 May – 15 October), private dock, kayaks, paddleboards, and expansive entertainment areas including a wrap-around porch and propane fire pit.
Minutes From Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C - Saint Michaels, MD
10 9 reviews

Minutes From Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C

apartment, Easton
This waterfront holiday home is situated in St. Michaels, just 3 kilometres from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it an ideal base for exploring this charming town. The property has received excellent ratings for its location, cleanliness, and overall experience.
The five-bedroom property spans 254 square metres and comfortably accommodates up to 10 guests. This spacious house offers a range of amenities including a private pool, a hot tub, a spa, a fitness centre, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.

Frequently asked questions about accommodations in Saint Michaels, MD

  • How can travelers reach Saint Michaels, MD?

    You can easily reach Saint Michaels by car, it's about a 2-hour drive from Baltimore or Washington, D.C. There's also a small airport nearby, Easton Airport, for those who prefer to fly.
  • 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.

  • What outdoor activities can visitors enjoy in and around Saint Michaels, MD?

    There are loads of ways to enjoy the outdoors! You can go kayaking or paddleboarding on the Miles River, take a scenic bike ride along the Chesapeake Bay, or go fishing on the pier at the harbour.
  • 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.

  • When is the ideal time to plan a trip to Saint Michaels, MD?

    Spring and autumn are lovely times to visit, with pleasant temperatures and fewer crowds. Summer gets busy, but it's great for enjoying the beaches and water activities. You can even visit during the winter for a quieter experience.
  • What are the best accommodations with a jacuzzi in Saint Michaels, MD?

    The best accommodations with a jacuzzi in Saint Michaels, MD are Inn At Perry Cabin, Parsonage Inn Bed And Breakfast and Beautiful Waterfront Home W\/ Pool In St - Michaels.

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

    The Saint Michaels Walking Trail is a great option for a leisurely stroll, and it's also perfect for cycling. You can also explore the scenic waterfront area, heading towards the harbour, for a beautiful walk.
  • What are the best accommodations for families and kids in Saint Michaels, MD?

  • What nearby towns or cities can be explored from Saint Michaels, MD?

    You can easily visit Easton, a charming town with a historic centre and plenty of shops and restaurants. It's about a 15-minute drive from Saint Michaels. You can also explore the Eastern Shore region, with its beautiful beaches and quaint towns.
  • 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 amenities can travelers expect from accommodations in Saint Michaels, MD?

    There are a range of accommodation options in Saint Michaels, from charming bed and breakfasts to comfortable hotels and resorts. Many places offer amenities like swimming pools, restaurants, and boat docks. It's a great place to relax and enjoy the beautiful surroundings.
  • 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.

Popular destinations

Best Saint Michaels, MD accommodations with a balcony

Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 3 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

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.
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.
Saint Michaels Summer Retreat With Pool & Hot Tub - Saint Michaels, MD
10 12 reviews

Saint Michaels Summer Retreat With Pool & Hot Tub

apartment, Tilghman Island
This waterfront apartment is located in McDaniel, just 3km from the town of St. Michaels, offering a peaceful retreat while still being close to local attractions. The apartment is ideal for families or groups of friends, with 3 bedrooms and 4 bathrooms, comfortably accommodating up to 6 guests.
The apartment boasts a modern and spacious interior with a fully equipped kitchen, a private swimming pool, and a jacuzzi, perfect for relaxing after a day exploring the island. Guests can also enjoy stunning views from the terrace or balcony, and take advantage of the shared dock for swimming, kayaking, or simply soaking up the sun.
Downtown Flat  Walk To Dining & Shops  Sleeps 4 - Saint Michaels, MD
10 2 reviews

Downtown Flat Walk To Dining & Shops Sleeps 4

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.

Best Saint Michaels, MD accommodations with a kitchen

Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres. - Saint Michaels, MD
10 21 reviews

Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres.

apartment, Stevensville
This Stevensville holiday home, less than 8 kilometres from the Chesapeake Bay Bridge, offers easy access to Annapolis and other Maryland attractions.
The four-bedroom, three-bathroom property sleeps ten guests and boasts a private 2-hectare wooded lot, a spacious deck, patios, a propane gas grill, and proximity to water activities including crabbing and fishing.
Tilghman | Fenced Yard | Pet Friendly | Charming - Saint Michaels, MD
9.3 6 reviews

Tilghman | Fenced Yard | Pet Friendly | Charming

apartment, Tilghman Island
This Tilghman Island holiday home is peacefully situated a short walk (under 1km) from Kronsberg Park and within a 2.4km radius of Knapp's Narrows Marina & Inn, the Talbot County Library Tilghman Branch, and the Phillips Wharf Environmental Center.
This 137 square metre property sleeps six guests in three bedrooms and two bathrooms, and boasts a fully equipped kitchen, Wi-Fi, private garden, parking, and a terrace; enjoy nearby boat tours and waterfront dining.
Minutes From Downtown St. Michaels | Guest House | Pool | Private Dock - Saint Michaels, MD
8.8 5 reviews

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

apartment, Oxford
This luxurious six-bedroom property, sleeping twelve, is situated near Saint Michaels, Maryland, approximately 5km from Saint Michaels Village and within 10km of St. Michaels Winery and the Classic Motor Museum; note that this is not Oxford as stated in the original listing.
The 224 square metre residence boasts a private pool, hot tub, spa, fully equipped kitchen, and free Wi-Fi, alongside four bathrooms and ample parking; washing machine facilities are also available.
Cottage #8 Shoreline Retreat Cottage - Saint Michaels, MD
9.7 34 reviews

Cottage #8 Shoreline Retreat Cottage

cottage, Tilghman Island
Herons Nest is a charming cottage located on Tilghman Island, just a short distance from the main house, offering a peaceful and secluded retreat. It has excellent user, location and cleanliness ratings.
The cottage is a self-catering property with one bedroom and one bathroom, accommodating up to six guests. Guests can enjoy a range of amenities including a full kitchen, a garden, parking and access to kayaks, canoes, paddle boats, a pier for fishing and crabbing, and a shared gazebo with a stereo, TV and microwave.
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