Best apartment offers in Saint Michaels, MD

28 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Saint Michaels, MD apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

28 Best apartments in Saint Michaels, MD

Find the Best Family-Friendly Self-Catering Apartments in Saint Michaels, MD

Kid-friendly holiday apartments in Saint Michaels, MD offer close proximity to lifeguarded beaches and plenty of room for the whole family to spread out.

Chesapeake Country Cottage: A Home Away From Home - Saint Michaels, MD
9.7 57 reviews
Saint Michaels, MD
08/08 – 10/08
£469/nighttotal: £938 (2 )

Chesapeake Country Cottage: A Home Away From Home

3 6
apartment , Easton
This waterfront apartment is located just a short drive from the historic towns of St. Michaels and Easton, offering a peaceful setting in a beautiful area. It has excellent user, location, and cleanliness ratings, making it a great option for travellers.
This charming home has three bedrooms and one bathroom, accommodating up to six guests. It offers a range of amenities, including a fully equipped kitchen, a living room with a wood-burning fireplace, a spacious outdoor area with a deck and a screened porch, a private pier and tidal cove, and a selection of recreational equipment such as kayaks, bicycles, and yard games.
Tilghman | Fenced Yard | Pet Friendly | Charming - Saint Michaels, MD
9.3 6 reviews
Saint Michaels, MD
24/06 – 28/06
£481/nighttotal: £1924 (4 )

Tilghman | Fenced Yard | Pet Friendly | Charming

3 3
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.
Tilghman | Pool | Private Dock | Pet Friendly - Saint Michaels, MD
9.4 15 reviews
Saint Michaels, MD
25/06 – 01/07
£709/nighttotal: £4254 (6 )

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.
Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD
10 6 reviews
Saint Michaels, MD
07/08 – 09/08
£600/nighttotal: £1200 (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.

Best Holiday Apartments with a Pool in Saint Michaels, MD

A holiday apartment with a swimming pool in Saint Michaels, MD is a brilliant base for a refreshing dip to complement a day by the water.

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.6 20 reviews
Saint Michaels, MD
24/06 – 28/06
£225/nighttotal: £900 (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.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
9.4 16 reviews
Saint Michaels, MD
24/06 – 28/06
£242/nighttotal: £968 (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.
Quailsar Farm | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
25/06 – 01/07
£891/nighttotal: £5346 (6 )

Quailsar Farm | An Esvr Property

5 4
apartment , Easton
Quailsar Farm is a 5-bedroom holiday home located in Talbot County, on Maryland's Eastern Shore, just a short drive from the charming town of Easton. The surrounding area is peaceful and rural, offering a tranquil escape from the hustle and bustle of city life.
The spacious property features a free-flowing layout, comfortably accommodating up to 10 guests. Amenities include a well-equipped kitchen, a swimming pool, and parking, making it ideal for families or groups of friends seeking a relaxing getaway.
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
£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.

Frequently asked questions about apartment rentals in Saint Michaels, MD

Destinations nearby

Best Saint Michaels, MD holiday apartments with air conditioning

A Willows Dream | An Esvr Property - Saint Michaels, MD
10 3 reviews
Saint Michaels, MD
08/08 – 10/08
£574/nighttotal: £1148 (2 )

A Willows Dream | An Esvr Property

2 6
apartment , Oxford
This Cape Cod-style holiday home in Oxford offers a peaceful rural retreat, its precise location and proximity to specific Oxford landmarks requiring further clarification.
The property boasts a spacious three-bedroom, two-bathroom layout sleeping six, complete with a well-equipped kitchen including a fridge, microwave, and dishwasher, a garden, air conditioning, and excellent guest ratings.
Kent Island Waterfront | Pool | Stunning View - Saint Michaels, MD
9.8 7 reviews
Saint Michaels, MD
25/06 – 29/06
£712/nighttotal: £2848 (4 )

Kent Island Waterfront | Pool | Stunning View

3 2
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.
Downtown St. Michaels | Porch + Pet-friendly - Saint Michaels, MD
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.
Relax On Kent Island In A 4 Bedroom Home W/waterview! - Saint Michaels, MD
9.8 324 reviews
Saint Michaels, MD
24/06 – 28/06
£363/nighttotal: £1452 (4 )

Relax On Kent Island In A 4 Bedroom Home W/waterview!

4 3
apartment , Stevensville
This Stevensville holiday home is conveniently located near Matapeake State Park (14.5km), Paul Reed Smith Guitars (14.5km), and Island Dog Park (14.5km), with Love Point State Park and the Chesapeake Bay Maritime Museum within 19km.
The 149 square metre property offers three bedrooms, sleeping up to eleven guests, and boasts a fully equipped kitchen, free Wi-Fi, a terrace, garden, parking and a smoke-free environment.

Guest-Favourite Pet-Friendly Holiday Apartments in Saint Michaels, MD

Enjoy stress-free seaside trips from a dog-friendly holiday apartment in Saint Michaels, MD near local beaches.

*Waterfront* 5br W/ Pool + Firepit On Kent Island! - Saint Michaels, MD
10 13 reviews
Saint Michaels, MD
27/06 – 28/06
£2016/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.
Bay Escape - Saint Michaels, MD
Saint Michaels, MD
08/08 – 10/08
£382/nighttotal: £764 (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.
Saved By The Bay | An Esvr Property - Saint Michaels, MD
10 5 reviews
Saint Michaels, MD
24/06 – 28/06
£644/nighttotal: £2576 (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.
Bayview 2.0 | An Esvr Property - Saint Michaels, MD
Saint Michaels, MD
19/07 – 22/07
£2387/nighttotal: £7161 (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.
©2026 cozycozy.com