Downtown St. Michaels | Bikes | Kayaks | Private Pier
3 2
apartment , Easton
This waterfront holiday home is situated in St. Michaels, a charming town just 16 kilometres from Easton, offering easy access to the Chesapeake Bay Maritime Museum and the St. Michaels Winery. The property enjoys excellent user, location and cleanliness ratings. This three-bedroom property spans 203 square metres and comfortably accommodates six guests. Enjoy stunning views, a cosy fireplace, a fully equipped kitchen, a private garden, a tennis court and a spa, all within a smoke-free environment.
Saint Michaels, MD
25/06 – 01/07
£703/nighttotal: £4218 (6 )
Clearview
1 4
house , Tilghman Island
Clearview, a holiday home on Tilghman Island, Maryland, is situated 39 kilometres from the Academy Art Museum and 121 kilometres from Baltimore/Washington International Thurgood Marshall Airport. This three-bedroom, three-bathroom property boasts 191 square metres of floor space, sleeps up to 11 guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free private parking.
9.2 16 reviews
Saint Michaels, MD
24/07 – 29/07
£656/nighttotal: £3280 (5 )
Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!
4 6
apartment , Oxford
This waterfront apartment is situated in Royal Oak, a peaceful area just 5km from Oxford, offering easy access to the charming village and its attractions. It has received excellent ratings from previous guests. The apartment is spacious, spanning 263 square metres and comfortably accommodating up to 8 guests. It boasts a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, a fitness centre, and parking, ensuring a relaxing and enjoyable stay.
10 1 review
Saint Michaels, MD
24/07 – 29/07
£619/nighttotal: £3095 (5 )
Waterfront, Hot Tub, Elevator. Waterfowl Special!
4 6
apartment , Oxford
This four-bedroom apartment is conveniently located just a short distance from Oxford, offering easy access to the city's attractions. The waterfront location provides stunning views and direct access to a sandy beach and a private dock. The apartment is spread over three levels, comfortably accommodating up to eight guests. The fully equipped kitchen, spacious living areas, and multiple bedrooms, including a master suite with a king-size bed, provide a relaxing and comfortable stay. Guests can enjoy the private hot tub, the recreational basement with a bar and Jacuzzi, and the elevator for easy access to all levels.
Saint Michaels, MD
25/06 – 01/07
£673/nighttotal: £4038 (6 )
Sunrise Cove
1 4
house , Oxford
This Oxford property, Sunrise Cove, is situated in Royal Oak, Maryland, approximately 12.6km from the Academy of the Arts and 50km from the Chesapeake Exploration Center, a convenient location for exploring the surrounding area. This spacious 234 square metre house boasts three bedrooms, two bathrooms, a private pool, Jacuzzi, free Wi-Fi and parking, accommodating up to 11 guests and offering self-catering facilities in its fully equipped kitchen.
9.6 7 reviews
Saint Michaels, MD
08/08 – 10/08
£612/nighttotal: £1224 (2 )
Downtown Oxford | Outdoor Dining | Character Filled
3 6
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.
9.0 4 reviews
Saint Michaels, MD
25/06 – 01/07
£854/nighttotal: £5124 (6 )
Minutes From Downtown Easton And St. Michaels | Pool | 1st Floor Bedroom | Pet F
5 4
apartment , Easton
Quailsar Farm is a vacation home situated in a sought-after area of Easton, Maryland, close to Avalon Theatre and The Third Haven Friends Meeting House. This property has earned an excellent user rating, making it a popular choice for travellers. The spacious 5-bedroom home spans 471 square metres and can comfortably accommodate up to 10 guests. This pet-friendly property offers a range of amenities, including a swimming pool, air conditioning, a fully-equipped kitchen, and a large garden.
Saint Michaels, MD
03/07 – 06/07
£271/nighttotal: £813 (3 )
Spacious Trappe Getaway With Outdoor Pool And Gazebo!
4 2
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.
9.5 24 reviews
Saint Michaels, MD
03/07 – 06/07
£269/nighttotal: £807 (3 )
Floating Yacht Home With Private Beach
1 2
boat , Stevensville
This luxury yacht, moored at Kentmorr Marina in Stevensville, Maryland, offers a unique stay just a short drive (approximately 20km) from Annapolis and its historic sites. The 12-metre vessel boasts two queen cabins each with an ensuite bathroom, accommodating up to eight guests, and features a fully equipped kitchen, karaoke machine, and private beach access with BBQ facilities.
10 1 review
Saint Michaels, MD
03/07 – 06/07
£340/nighttotal: £1020 (3 )
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.
Saint Michaels, MD
24/07 – 29/07
£573/nighttotal: £2865 (5 )
Ferry View
1 6
house , Oxford
Ferry View, a spacious Oxford house, is situated 18 kilometres from the Ruskin School of Art and 100 kilometres from Baltimore–Washington International Thurgood Marshall Airport. This 331-square-metre property boasts four bedrooms, four bathrooms, free Wi-Fi, private parking, and comfortably accommodates up to 15 guests.
10 2 reviews
Saint Michaels, MD
25/06 – 01/07
£2586/nighttotal: £15516 (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.
Best Saint Michaels, MD accommodations with a balcony
10 32 reviews
Saint Michaels, MD
24/07 – 29/07
£2366/nighttotal: £11830 (5 )
Ranch At Royal Oak- Exclusive Waterfront Pool Pier
6 6
apartment , Oxford
This waterfront property is situated just 14.5 kilometres from St. Michaels Winery, Chesapeake Bay Maritime Museum, and St. Michaels Museum, offering easy access to the vibrant attractions of Oxford. The house has consistently received excellent ratings from previous guests, highlighting its quality and appeal. This spacious home spans 427 square metres and comfortably accommodates up to 12 guests, making it ideal for large families or groups. The property boasts an array of amenities for a comfortable stay, including a private swimming pool, a spa, and a fully equipped kitchen, as well as a dedicated games room and outdoor barbecue facilities for entertainment.
10 129 reviews
Saint Michaels, MD
08/08 – 10/08
£941/nighttotal: £1882 (2 )
Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues
4 6
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.
9.6 119 reviews
Saint Michaels, MD
24/08 – 28/08
£282/nighttotal: £1128 (4 )
Dollhouse In Central Historic St Michaels
2 2
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.
10 4 reviews
Saint Michaels, MD
28/06 – 01/07
£591/nighttotal: £1773 (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.
Best family friendly Saint Michaels, MD lodging
Among the 46 accommodations in Saint Michaels, MD, here are the 4 best for families
10 56 reviews
Saint Michaels, MD
24/07 – 29/07
£1962/nighttotal: £9810 (5 )
Ranch At Royal Oak Exclusive Waterfront Pool Pier
6 6
apartment , Oxford
The Ranch at Royal Oak is a luxurious holiday home situated on a private peninsula in Talbot County, Maryland, just 10km from the historic town of St. Michaels and 15km from Easton, offering a tranquil escape close to charming towns. The property has received excellent ratings for location, cleanliness and user experience. The spacious property has 6 bedrooms and 6 bathrooms, accommodating up to 12 guests. Guests can enjoy a range of amenities including a swimming pool, garden, parking, air conditioning, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as access to the internet.
10 31 reviews
Saint Michaels, MD
01/07 – 05/07
£1073/nighttotal: £4292 (4 )
25-50% Off~private Beach~hot Tub~fire Table~
3 2
apartment , Stevensville
This Stevensville beachfront property, situated next to a golf course and steps from Romancoke Wharf County Park, offers easy access to Matapeake State Park (14.5 km) and Love Point State Park (19.3 km). This 121 square metre house sleeps seven guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, a jacuzzi, a terrace, a garden, free Wi-Fi, and on-site parking.
9.8 6 reviews
Saint Michaels, MD
24/07 – 29/07
£626/nighttotal: £3130 (5 )
Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien
5 6
apartment , Oxford
This luxurious five-bedroom waterfront property near Oxford is situated approximately 3km from the Oxford Museum and 4km from Play Ball Dog Park, offering scenic views and easy access to St Michael's Village and St Michael's Winery within a 14.5km radius. Boasting 331 square metres of floor space, this self-catering house sleeps eight guests and includes four bathrooms, a complete kitchen with dishwasher, a terrace, garden, spa, parking, and free Wi-Fi.
9.9 88 reviews
Saint Michaels, MD
08/08 – 10/08
£852/nighttotal: £1704 (2 )
Kent Island Beach House Ii By Kentmorr Marina
4 6
apartment , Stevensville
KI Beach House II, a Stevensville holiday home on Kent Island, Maryland, is located minutes from the Kent Narrows and a kilometre from the Blue Heron Golf Course. This 209-square-metre property sleeps up to 14 guests in four bedrooms, offering a modern fisherman's village aesthetic, Chesapeake Bay views, and amenities including a fully equipped kitchen, BBQ grills, and access to the South Island Trail; bikes are available for stays of three nights or more during peak season.
Frequently asked questions about accommodations in Saint Michaels, MD
What are the must-see sites in or near Saint Michaels, MD?
Saint Michaels is a charming town with plenty to see. The Chesapeake Bay Maritime Museum is a must-visit, showcasing the region's rich maritime history. The town's historic district is lovely to explore, with quaint shops and restaurants. For a scenic drive, head to the Eastern Neck National Wildlife Refuge for a chance to spot bald eagles and other wildlife.
What are the best places to stay in Saint Michaels, MD?
The easiest way to get to Saint Michaels is by car. It's about a two-hour drive from Baltimore and a three-hour drive from Washington, D.C. You can also fly into the Easton Airport, which is about a 20-minute drive from Saint Michaels. There's a ferry service from Annapolis, if you're looking for a scenic route.
What are the best places to stay with a pool in Saint Michaels, MD?
What outdoor activities can visitors enjoy in and around Saint Michaels, MD?
Saint Michaels is a great place to enjoy the outdoors. You can go boating, fishing, kayaking, or paddleboarding on the Chesapeake Bay. The town also has a lovely waterfront park, perfect for a picnic or a stroll. If you're feeling adventurous, you can hike or bike the scenic trails at the Eastern Neck National Wildlife Refuge.
What are the best places to stay with a jacuzzi 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 Saint Michaels. The weather is mild, and the crowds are smaller. Summer is a popular time to visit, but it can get hot and humid. If you're looking for a festive atmosphere, come during the Christmas season when the town is beautifully decorated.
What are the best places to stay for families and kids in Saint Michaels, MD?
What are the best walking or cycling routes in Saint Michaels, MD?
A popular walking route is along the waterfront, starting from the Chesapeake Bay Maritime Museum and continuing along the harbour. For cycling, you can enjoy the scenic route along the Miles River, which offers beautiful views of the water and surrounding countryside.
What are the best pet friendly places to stay in Saint Michaels, MD?
What nearby towns or cities can be explored from Saint Michaels, MD?
There are plenty of interesting places to explore within a short drive from Saint Michaels. Easton is a charming town just 15 minutes away, with a vibrant arts scene and historic architecture. Annapolis, the state capital of Maryland, is about an hour away and offers a wealth of historical sites and attractions.
What are the best places to stay with parking in Saint Michaels, MD?
What amenities can travelers expect from accommodations in Saint Michaels, MD?
You'll find a variety of accommodations in Saint Michaels, from cozy bed and breakfasts to waterfront hotels. Many places offer amenities like swimming pools, fitness centres, and restaurants. Some also have boat docks, perfect for those who want to bring their own boat.
Destinations nearby
Discover Lodgings by the Sea in Saint Michaels, MD
Base your next maritime holiday at coastal lodging in Saint Michaels, MD, located short distances from local shorelines.
10 5 reviews
Saint Michaels, MD
27/06 – 28/06
£384/nightfor 1 night
40' Classic Bristol Sailboat
1 2
boat , Stevensville
This historic 45-year-old Bristol B 40 Yawl, a unique boat accommodation, is moored in a quiet, protected marina on a lagoon, offering expansive nature views and a short distance to Stevensville's attractions. This stationary vessel provides a peaceful stay for up to three guests with its luxurious teak and mahogany interior, featuring a kitchen and internet, ideal for relaxation and enjoying sunrise and sunset views over the water.
Best Saint Michaels, MD accommodations with a kitchen
10 3 reviews
Saint Michaels, MD
03/07 – 06/07
£813/nighttotal: £2439 (3 )
Three Decks Overlook Marina Basin And Views Of The Chesapeake And Eastern Bays
6 2
apartment , Shady Side
This six-bedroom apartment is situated in Stevensville, a short walk from the beach and within walking distance of the marina, offering easy access to the Chesapeake Bay's attractions. The property boasts multiple decks with picturesque views, a spacious entertainment area with a pool table, bar, and poker table, and comfortably accommodates up to 12 guests.
9.9 140 reviews
Saint Michaels, MD
28/06 – 01/07
£333/nighttotal: £999 (3 )
Blue Crab Lodge
1 2
apartment , Easton
This charming apartment is situated in the heart of St. Michaels, just a short walk from the waterfront, shops, and restaurants. The apartment has received excellent ratings for location, cleanliness, and overall experience. The flat is perfect for families or groups of up to six people, with two bedrooms and one bathroom. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, and parking.
Saint Michaels, MD
07/08 – 09/08
£543/nighttotal: £1086 (2 )
Downtown St. Michaels | Porch + Pet-friendly
1 2
apartment , Easton
This studio flat is located in the central district of St. Michaels, a mere 100 metres from its boutiques, seafood restaurants, and harbour, offering authentic historic charm with exposed wood beams and coastal décor. This pet-friendly accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a private terrace, and dedicated parking, with keyless entry for convenience.
9.9 91 reviews
Saint Michaels, MD
24/08 – 28/08
£240/nighttotal: £960 (4 )
Charming Apt. In St. Michaels
1 2
apartment , Easton
This Easton studio apartment, a renovated 1850s McMillian House unit in St Michael's historic district on Talbot Street, is situated steps from the Miles River and numerous shops, museums, and restaurants. The two-storey self-catering apartment, sleeping four, features a queen bed, full-size sofa bed, kitchenette, free Wi-Fi, YouTube TV, and dedicated parking for two cars; guests can also enjoy a shared front porch and the owners provide local recommendations.
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
Saint Michaels, MD
25/06 – 01/07
£891/nighttotal: £5346 (6 )
Quailsar Farm | An Esvr Property
5 4
apartment , Easton
9.5 12 reviews
Saint Michaels, MD
24/08 – 28/08
£786/nighttotal: £3144 (4 )
Bankors Aweigh | An Esvr Property
1 2
apartment , Tilghman Island
9.2 76 reviews
Saint Michaels, MD
01/07 – 05/07
£282/nighttotal: £1128 (4 )
Kent Island Resort
1 2
island , Stevensville
Saint Michaels, MD
25/06 – 01/07
£2618/nighttotal: £15708 (6 )
Fairview Estate
1 4
house , Easton
Top Accommodations with Free Parking in Saint Michaels, MD
Having a car park at your accommodation in Saint Michaels, MD ensures the coast and local beaches are easy to reach every day with no extra faff.
9.3 6 reviews
Saint Michaels, MD
25/06 – 01/07
£401/nighttotal: £2406 (6 )
Tilghman | Fenced Yard | Pet Friendly | Charming
3 4
apartment , Tilghman Island
9.6 128 reviews
Saint Michaels, MD
24/08 – 28/08
£333/nighttotal: £1332 (4 )
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!
2 2
cottage , Easton
8.6 21 reviews
Saint Michaels, MD
25/06 – 01/07
£708/nighttotal: £4248 (6 )
Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Private Dock |
3 4
apartment , Oxford
9.8 10 reviews
Saint Michaels, MD
24/08 – 28/08
£443/nighttotal: £1772 (4 )
Elegant 2-bedroom Retreat In Historic Saint Michaels Walk To Dining & Shops
2 2
apartment , Easton
Popular Places to Stay with a Hot Tub in Saint Michaels, MD
Enjoy the simple pleasure of a private hot tub soak to round off a perfect day spent by the water in Saint Michaels, MD.
9.7 15 reviews
Saint Michaels, MD
28/06 – 01/07
£862/nighttotal: £2586 (3 )
Waterfront - 3 Luxury Bdrms W/ Outside Pool & Spa
1 2
apartment , Tilghman Island
9.9 22 reviews
Saint Michaels, MD
08/08 – 10/08
£489/nighttotal: £978 (2 )
Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba
3 6
apartment , Grasonville
Saint Michaels, MD
24/08 – 28/08
£776/nighttotal: £3104 (4 )
Bankors Aweigh
1 2
house , Tilghman Island
8.0 2 reviews
Saint Michaels, MD
24/08 – 28/08
£848/nighttotal: £3392 (4 )
Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock
