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.
10 1 review
Saint Michaels, MD
09/10 – 11/10
A$1008/nighttotal: A$2016 (2 )
Ships Ahoy | An Esvr Property
3 4
apartment , Oxford
This newly renovated Oxford apartment, situated on the Eastern Shore, offers easy access to local attractions; precise distances are not specified. The three-bedroom, two-bathroom property sleeps six, featuring a free-flowing floor plan, a fully equipped kitchen with dishwasher, air conditioning, parking, and complimentary Wi-Fi.
10 3 reviews
Saint Michaels, MD
09/10 – 11/10
A$500/nighttotal: A$1000 (2 )
#2 Egret Cottage Harris Cove
1 4
cottage , Tilghman Island
This lakefront holiday home is situated near Tilghman Island, Maryland, approximately 18 kilometres from St. Michaels Marina and the Chesapeake Bay Maritime Museum. The single-bedroom property sleeps four guests and includes air conditioning, Wi-Fi, a barbecue, and on-site parking, with easy access to local attractions such as the St. Michaels Museum and Neavitt Park.
10 6 reviews
Saint Michaels, MD
09/10 – 11/10
A$1106/nighttotal: A$2212 (2 )
Grace Cottage, St Michaels Walk To Everything!
2 4
apartment , Easton
This St. Michaels apartment is located in the historic district, offering easy walking access to local shops, restaurants, and the waterfront, with a private driveway accommodating two vehicles. This two-bedroom, two-bathroom flat for four guests features a newly renovated kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and a large private garden with a fire pit and grill.
8.0 2 reviews
Saint Michaels, MD
09/10 – 11/10
A$1046/nighttotal: A$2092 (2 )
Down By The Docks | An Esvr Property
3 4
apartment , Oxford
This Oxford duplex, located within walking distance of Oxford city centre, offers easy access to shops, restaurants, and attractions. The three-bedroom, two-bathroom property sleeps six guests and includes a fully equipped kitchen with dishwasher, a garden, and Wi-Fi; pets are welcome.
This luxurious waterfront property, near Easton and Saint Michaels, Maryland (approximately 160km from Oxford, England; note that this listing incorrectly states Oxford as the destination), offers a family-friendly escape on an 18-acre private retreat. The four-bedroom, two-bathroom dwelling sleeps eight guests and boasts a fully equipped kitchen, swimming pool, fitness centre, and access to kayaks, fishing equipment, and a petting zoo.
10 7 reviews
Saint Michaels, MD
29/08 – 04/09
A$315/nighttotal: A$1890 (6 )
Cozy Getaway! Centrally Located Between St. Michaels And Tilghman Island
3 5
apartment , Tilghman Island
This three-bedroom house, sleeping up to six guests, is situated on Tilghman Island in Talbot County, Maryland, offering easy access to the Tilghman Watermen's Museum and Chesapeake Bay Maritime Museum (distances unspecified). The property features Wi-Fi, a washing machine, air conditioning, a queen bed, a double bed, and bunk beds, providing comfortable accommodation for families or small groups visiting the island.
10 1 review
Saint Michaels, MD
24/06 – 28/06
A$1105/nighttotal: A$4420 (4 )
Royal Oak House
1 3
apartment , Oxford
This three-bedroom house near St Michaels and Easton, Maryland, offers easy access to local amenities and is a short drive from Oxford. The pet-friendly property sleeps six, includes a fully equipped kitchen, air conditioning, parking, and internet access; a starter supply of essentials is provided.
10 3 reviews
Saint Michaels, MD
31/07 – 06/08
A$1421/nighttotal: A$8526 (6 )
Three Decks Overlook Marina Basin And Views Of The Chesapeake And Eastern Bays
6 11
apartment , Stevensville
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.
9.7 34 reviews
Saint Michaels, MD
29/08 – 04/09
A$512/nighttotal: A$3072 (6 )
Cottage #8 Shoreline Retreat Cottage
1 5
apartment , 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.
9.7 279 reviews
Saint Michaels, MD
24/06 – 28/06
A$430/nighttotal: A$1720 (4 )
Perfect Waterview Cottage - St. Michaels Getaway
2 3
cottage , Tilghman Island
Shipwright Cottage is located in the Bay Hundred area of Tilghman Island, just 13km from the town of St. Michaels. This charming property has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage offers 111 square metres of space, comfortably accommodating up to four guests in its two bedrooms. The cottage is equipped with a modern kitchen, WiFi, a DVD player, a washing machine and dryer, a charcoal grill, a screened porch, and access to kayaks, bicycles, and a bike trailer.
9.9 22 reviews
Saint Michaels, MD
09/10 – 11/10
A$1013/nighttotal: A$2026 (2 )
Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba
3 4
apartment , Grasonville
This Prospect Bay Country Club apartment in Grasonville, Maryland, is located 24 kilometres east of the Chesapeake Bay Bridge, offering easy access to the Chesapeake Bay and its attractions. This spacious 3200 sq ft (approx. 297 sq m) three-bedroom, three-and-a-half-bathroom property sleeps six guests and boasts a private hot tub, creek views, access to country club amenities (including a pool and golf course), and proximity to a marina.
Saint Michaels, MD: Best accommodations with a pool
Among the 46 accommodations in the area, here is the list of the 4 best ones with a pool
9.8 116 reviews
Saint Michaels, MD
09/10 – 11/10
A$2841/nighttotal: A$5682 (2 )
Waterfront Estate With Pool, Pier & Privacy
1 4
apartment , Grasonville
This luxurious retreat is situated on the beautiful Wye River in Grasonville, Maryland, just 64 kilometres from Annapolis and St. Michaels, offering a peaceful escape in a stunning natural setting. This property has received excellent ratings for location, cleanliness, and user experience. This spacious house has seven bedrooms and eight bathrooms, accommodating up to sixteen guests. It boasts a fully-equipped kitchen, a private pool, a tennis court, a pier, and a boat ramp, providing plenty of space for relaxation and entertainment.
Saint Michaels, MD
31/07 – 06/08
A$1137/nighttotal: A$6822 (6 )
Waterfront Family Retreat - Mins From St. Michaels
1 11
apartment , Oxford
This waterside property offers a tranquil escape in Oxford, located a 15-minute drive from the city centre's historic university colleges and museums. This six-bedroom, four-bathroom flat accommodates up to 12 guests and features a chef-ready kitchen, a private dock for crabbing and fishing, an outdoor entertainment area with a pool and spa, and a fenced yard with a play area.
Saint Michaels, MD
19/06 – 23/06
A$1783/nighttotal: A$7132 (4 )
Quailsar Farm
1 2
house , Easton
This Easton property, Quailsar Farm, is situated 5km from the Academy of the Arts, offering easy access to the Chesapeake Bay region's attractions, including Federalsburg Marina (37km) and the Chesapeake Exploration Centre (40km). This 471 square metre house boasts five bedrooms, four bathrooms, a private pool, free Wi-Fi, private parking, and a fully equipped kitchen, comfortably accommodating up to 19 guests.
Saint Michaels, MD
24/06 – 28/06
A$466/nighttotal: A$1864 (4 )
Spacious Trappe Getaway With Outdoor Pool And Gazebo!
4 3
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.
Saint Michaels, MD: Best family friendly accommodations
Among the 46 accommodations in the area, here is the list of the 4 best family friendly ones
10 68 reviews
Saint Michaels, MD
09/10 – 11/10
A$1871/nighttotal: A$3742 (2 )
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly
2 4
cottage , Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore. The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.
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.
9.7 57 reviews
Saint Michaels, MD
19/06 – 23/06
A$823/nighttotal: A$3292 (4 )
Chesapeake Country Cottage: A Home Away From Home
3 2
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.
10 48 reviews
Saint Michaels, MD
19/06 – 23/06
A$662/nighttotal: A$2648 (4 )
Eastern Shore Retreat!
1 2
apartment , Easton
This three-bedroom apartment is located on Maryland's Eastern Shore, just minutes from the charming towns of Easton, Oxford, and St. Michaels. It has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. This spacious home has two bathrooms and can accommodate up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private garden, and a ping pong table for entertainment, as well as water views, a sunporch, and a large deck for relaxing.
Frequently asked questions about accommodations in Saint Michaels, MD
What are the must-see sites in or near Saint Michaels, MD?
Well, you absolutely have to visit the Chesapeake Bay Maritime Museum, it's a real gem, and you can't miss the charming shops and restaurants on the waterfront. If you're up for a drive, take a trip to the Eastern Shore's historic town of Easton, it's a lovely spot.
What are the best accommodations in Saint Michaels, MD?
The easiest way to get to Saint Michaels is by car, it's a pleasant drive from Baltimore or Washington D.C. You can also fly into Salisbury-Ocean City Wicomico Regional Airport, which is about a 45-minute drive away. There's also a ferry service from Annapolis, which is a fun way to arrive.
What are the best accommodations 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 kayaking or paddleboarding on the Miles River, take a scenic bike ride along the waterfront, or go for a hike in the nearby Blackwater National Wildlife Refuge. There's also a great boat launch at the harbour.
What are the best accommodations with a jacuzzi in Saint Michaels, MD?
When is the ideal time to plan a trip to Saint Michaels, MD?
Spring and autumn are the best times to visit Saint Michaels, the weather is mild and the crowds are smaller. You'll see beautiful colours in the fall, and the spring is lovely too.
What are the best accommodations for families and kids in Saint Michaels, MD?
What are the best walking or cycling routes in Saint Michaels, MD?
The waterfront walk is a lovely stroll, it takes you past the harbour and the historic buildings. For a longer bike ride, you can follow the scenic route along the Miles River, it's about 10km long and offers stunning views.
What are the best pet friendly accommodations in Saint Michaels, MD?
What nearby towns or cities can be explored from Saint Michaels, MD?
There are several charming towns and cities within easy driving distance of Saint Michaels. You can visit Easton, which is about 30 minutes away, or explore the historic town of Annapolis, which is about an hour away. Cambridge is also worth a visit.
What are the best accommodations with parking in Saint Michaels, MD?
What amenities can travelers expect from accommodations in Saint Michaels, MD?
You'll find a range of accommodation options in Saint Michaels, from charming bed and breakfasts to luxury hotels. Many of the accommodations offer amenities like swimming pools, restaurants, and even boat docks. There are also plenty of holiday homes and apartments available to rent.
Destinations nearby
Best Saint Michaels, MD accommodations with a balcony
10 37 reviews
Saint Michaels, MD
25/06 – 29/06
A$510/nighttotal: A$2040 (4 )
Harbor View Suite\ntalbot County License Number Strn-25-58
1 2
apartment , Easton
This Saint Michaels suite, a short walk from the Chesapeake Bay Maritime Museum and the St. Michaels Museum, offers stunning harbour views and proximity to Lyons Distilling Company within the Old Mill complex. The 45-square-metre apartment includes a king-size bed, sofa, and a kitchenette with a fridge, freezer, microwave, and coffee makers, accommodating two guests and featuring a private bathroom and off-street parking.
10 41 reviews
Saint Michaels, MD
31/07 – 06/08
A$1629/nighttotal: A$9774 (6 )
Stay By Md's Chesapeake Bay This Father's Day! Walk To Marina & Restaurant.
5 11
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.
9.6 12 reviews
Saint Michaels, MD
19/06 – 23/06
A$645/nighttotal: A$2580 (4 )
Pet-friendly Summer Retreat On Tilghman
3 2
apartment , Tilghman Island
This three-bedroom cottage in Tilghman Island, a rural area renowned for its Chesapeake Bay connections, offers easy access to marinas, waterfront dining, and cultural sites such as the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum, all within a 2 kilometre radius. This pet-friendly accommodation accommodates six guests and features a private pool, a large screened porch with dining facilities, a fully equipped kitchen, and keyless entry, ensuring a comfortable stay with ample amenities and nearby activities.
9.6 119 reviews
Saint Michaels, MD
24/06 – 28/06
A$517/nighttotal: A$2068 (4 )
Dollhouse In Central Historic St Michaels
2 3
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.
Best Saint Michaels, MD accommodations with a kitchen
10 1 review
Saint Michaels, MD
31/07 – 06/08
A$1356/nighttotal: A$8136 (6 )
Chesapeake Bay Overlook Home
1 11
apartment , Shady Side
This Shady Side holiday home is located near the Chesapeake Bay and marina, within walking distance of the beach. Sleeping up to 12 guests, this six-bedroom, three-bathroom property boasts a fully equipped kitchen, laundry facilities, a large entertainment room with a pool table and bar, and stunning Chesapeake Bay views from three expansive decks; nearby attractions include fresh seafood at the marina.
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.
8.6 21 reviews
Saint Michaels, MD
19/06 – 23/06
A$1432/nighttotal: A$5728 (4 )
Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Private Dock |
3 2
apartment , Oxford
This waterfront property is located just 3km from St. Michaels Winery and within 6km of the Chesapeake Bay Maritime Museum and St. Michaels Museum, offering easy access to local attractions and a peaceful setting by the water. The house has received very good user ratings for cleanliness and an excellent location rating. This 3-bedroom, 2-bathroom house is ideal for families or groups of up to 6 people, offering 234 square metres of space. The property is equipped with a private pool, a spa tub, a fireplace, a fully equipped kitchen, a washing machine, a tennis court, and a garden, providing a comfortable and enjoyable stay.
9.8 9 reviews
Saint Michaels, MD
09/10 – 11/10
A$1012/nighttotal: A$2024 (2 )
Elegant 2-bedroom Retreat In Historic Saint Michaels Walk To Dining & Shops
2 4
apartment , Easton
This St. Michaels apartment, a short distance from Easton, is conveniently located within a 0.8km radius of Higgins Yacht Yard and Marina, St. Michaels Town Hall, and St. Michaels Marina, offering easy access to the Chesapeake Bay Maritime Museum and Muskrat Park. The two-bedroom, one-bathroom flat sleeps four, includes parking, internet access, a refrigerator, microwave, and is a smoke-free property.
