Best apartment offers in Saint Michaels, MD

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Saint Michaels, MD apartments
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28 Holiday apartments in Saint Michaels, MD

Best family friendly Saint Michaels, MD Holiday Apartments

Among the 28 accommodations in Saint Michaels, MD, here are the 4 best family friendly holiday apartments

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.4 16 reviews
Saint Michaels, MD
24/06 – 28/06
A$462/nighttotal: A$1848 (4 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 3
apartment , Trappe
This Trappe holiday home, situated within 9.6km of the Third Haven Friends Meeting House, Academy Art Museum, and Academy of the Arts, offers convenient access to local attractions and amenities.
This five-bedroom, three-bathroom property boasts 204 square metres of living space, including a private pool, fully equipped kitchen, and can comfortably accommodate eight guests.
Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres. - Saint Michaels, MD
10 17 reviews
Saint Michaels, MD
08/08 – 10/08
A$1180/nighttotal: A$2360 (2 )

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

4 6
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 | Pool | Private Dock | Pet Friendly - Saint Michaels, MD
9.4 15 reviews
Saint Michaels, MD
27/06 – 04/07
A$1285/nighttotal: A$8995 (7 )

Tilghman | Pool | Private Dock | Pet Friendly

3 4
apartment , Tilghman Island
This waterfront property on Tilghman Island is just 0.3 miles from the Tilghman Watermen’s Museum and within easy reach of other attractions like the Chesapeake Bay Maritime Museum and St. Michaels Museum. The house has consistently received excellent ratings for location, cleanliness, and overall experience.
The property offers 191 square metres of space, accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. Guests can enjoy a private pool, a spa tub, a garden, a terrace, a barbecue, and modern amenities like free Wi-Fi and a fully equipped kitchen.
Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues - Saint Michaels, MD
10 129 reviews
Saint Michaels, MD
31/07 – 03/08
A$1542/nighttotal: A$4626 (3 )

Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues

1 10
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.

Best Holiday Apartments in Saint Michaels, MD with a pool

Among the 28 accommodations in Saint Michaels, MD, here are the 4 best apartments with a pool

Skipjack House | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
27/06 – 04/07
A$1058/nighttotal: A$7406 (7 )

Skipjack House | An Esvr Property

3 4
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.
Minutes From Downtown Easton And St. Michaels | Pool | 1st Floor Bedroom | Pet F - Saint Michaels, MD
9.0 4 reviews
Saint Michaels, MD
25/06 – 01/07
A$1627/nighttotal: A$9762 (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.
Saved By The Bay | An Esvr Property - Saint Michaels, MD
10 5 reviews
Saint Michaels, MD
24/06 – 28/06
A$1228/nighttotal: A$4912 (4 )

Saved By The Bay | An Esvr Property

3 3
apartment , Stevensville
This waterfront flat in Stevensville offers direct views of the Chesapeake Bay and Kent Island's waterways, placing you within 100 meters of the water's edge.
This 3-bedroom, 2-bathroom property accommodates up to 7 guests and features a renovated kitchen, air conditioning, and a communal swimming pool, with concierge services available for booking local activities.
Kent Island Waterfront | Pool | Stunning View - Saint Michaels, MD
9.8 7 reviews
Saint Michaels, MD
24/06 – 28/06
A$1326/nighttotal: A$5304 (4 )

Kent Island Waterfront | Pool | Stunning View

3 3
apartment , Stevensville
This Stevensville waterfront holiday home, in Queen Anne's County, Maryland, is a 3-5 minute drive from the Cross Island Trail, Blue Heron Golf Course, and Mowbray Park, offering easy access to local amenities.
The 127-square-metre (approximately 1367 square feet) property boasts three bedrooms sleeping seven, a renovated kitchen with granite countertops and stainless steel appliances, a private pool (open May 15th to October 15th), four kayaks, crabbing gear, and a charcoal grill; guests can also enjoy mesmerizing views of Kent Island's waterways.

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Best Saint Michaels, MD holiday apartments with air conditioning

Chic 3 Br / 2 Ba Cottage Near Chesapeake Bay - Saint Michaels, MD
10 48 reviews
Saint Michaels, MD
25/06 – 29/06
A$599/nighttotal: A$2396 (4 )

Chic 3 Br / 2 Ba Cottage Near Chesapeake Bay

1 2
apartment , Stevensville
This charming three-bedroom cottage is situated on Kent Island, Maryland, just 10 kilometres from the Bay Bridge and within easy reach of Annapolis, Washington D.C. and Baltimore. It has received excellent ratings for location, cleanliness and user experience.
The property offers a comfortable and stylish space for up to six guests with a spacious kitchen, two bathrooms and a dedicated workspace in the main bedroom. It is perfect for families, with a full bed in the second bedroom and twin bunk beds in the third, and features a peaceful location, stylish décor, relaxation amenities, and a well-equipped kitchen.
*Waterfront* 5br W/ Pool + Firepit On Kent Island! - Saint Michaels, MD
10 13 reviews
Saint Michaels, MD
27/06 – 28/06
A$3842/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.
Kent Island Beach House Ii By Kentmorr Marina - Saint Michaels, MD
9.9 88 reviews
Saint Michaels, MD
31/07 – 06/08
A$1542/nighttotal: A$9252 (6 )

Kent Island Beach House Ii By Kentmorr Marina

1 11
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.
Minutes From Downtown St. Michaels | Private Boat Ramp | Dock - Saint Michaels, MD
Saint Michaels, MD
24/06 – 28/06
A$1116/nighttotal: A$4464 (4 )

Minutes From Downtown St. Michaels | Private Boat Ramp | Dock

3 3
apartment , Tilghman Island
This waterfront property on Tilghman Island is located within 15km of Neavitt Park, Perry Cabin Park, and CL Open Field, and also within 15km of St Michaels Town Hall and Higgins Yacht Yard and Marina.
This three-bedroom, three-bathroom holiday home boasts 207 square metres of floor space, sleeps six guests, and includes a fully equipped kitchen, spa, free Wi-Fi, laundry facilities, and barbecue grills.

Best pet-friendly Saint Michaels, MD holiday apartments

Among the 28 accommodations in Saint Michaels, MD, here are the 4 best pet friendly holiday apartments

5-bedroom Waterfront Home On 1.5 Acres In  Stevensville With Tons Of Parking - Saint Michaels, MD
Saint Michaels, MD
08/08 – 10/08
A$1335/nighttotal: A$2670 (2 )

5-bedroom Waterfront Home On 1.5 Acres In Stevensville With Tons Of Parking

5 6
apartment , Stevensville
This five-bedroom country house in Stevensville offers convenient access to the Chesapeake Bay and Matapeake State Park, with attractions such as Paul Reed Smith Guitars and the Annapolis Maritime Museum within easy reach.
This spacious property accommodates up to 10 guests and features four bathrooms, air conditioning, and is located 4.9 kilometers from Tose Family Tennis Center and 8.7 kilometers from Alumni Hall.
Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
Saint Michaels, MD
07/08 – 09/08
A$1034/nighttotal: A$2068 (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.
Modern Island Escape By The Bay - Saint Michaels, MD
9.9 81 reviews
Saint Michaels, MD
31/07 – 06/08
A$846/nighttotal: A$5076 (6 )

Modern Island Escape By The Bay

5 11
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.
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
A$4930/nighttotal: A$29580 (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.
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