What is the best time to visit Saint Michaels, MD?

The best time to visit is during the spring or fall when the weather is mild and the crowds are smaller. The summer months are hot and humid, and the winter months can be chilly, but if you don't mind the cold, it's a beautiful time to see the town.

What are the best villa rentals in Saint Michaels, MD?

Among the villa rentals in Saint Michaels, MD, St - Michaels-historic Dist - Margaret Wells House , Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the most popular ones.

When is it easiest to book a villa rental in Saint Michaels, MD?

You'll find the best deals on villa rentals during the shoulder seasons, which are spring and fall. The summer months are the most popular time to visit, so book your villa rental early if you want to come during that time.

What are the best villa rentals with a pool in Saint Michaels, MD?

Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town , Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town are the best villa rentals with a pool in Saint Michaels, MD.

What are the top hiking trails near Saint Michaels, MD?

There aren't any hiking trails right in Saint Michaels, but if you're willing to drive a little, you can find some great hiking trails at the Blackwater National Wildlife Refuge, which is about 30 minutes away. You can also hike around the Chesapeake Bay Maritime Museum.

What are the best villa rentals with a jacuzzi in Saint Michaels, MD?

The best villa rentals with a jacuzzi in Saint Michaels, MD are Cottage On Solitude Creek - Hot Tub - Pool & Firepit , Suuri Rantahotelli - Josta On Henkeäsalpaavat Näkymät Auringonlaskuun and Minutes From Downtown St - Michael's | Game Room | Pool | Hot Tub | Pickle Ball C .

What are the advantages of renting a house or a villa in Saint Michaels, MD

Renting a house or villa gives you more space and privacy than staying in a hotel. You'll also have access to a kitchen, so you can save money by cooking your own meals. Many rentals are located right on the water, offering beautiful views and easy access to the harbor.

What are the best villa rentals for families and kids in Saint Michaels, MD?

The best villa rentals for families and kids in Saint Michaels, MD are St - Michaels-historic Dist - Margaret Wells House , Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Gorgeous Cottage: Easy Walk Into St Michaels Town .

Are there popular destinations near Saint Michaels, MD?

Yes, there are many popular destinations near Saint Michaels. The Eastern Shore is full of charming towns, and you can easily visit Annapolis, Baltimore, and even Washington D.C. for a day trip. The Chesapeake Bay is also a great place to explore by boat.

What are the best pet friendly villa rentals in Saint Michaels, MD?

The best pet friendly villa rentals in Saint Michaels, MD are Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town , Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town .

What are the best villa rentals with parking in Saint Michaels, MD?

St - Michaels-historic Dist - Margaret Wells House , Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the best villa rentals with parking in Saint Michaels, MD.

Saint Michaels, MD Villas and Beach house

9.7 146 reviews

Saint Michaels, MD

06/25 – 06/29

$211/nighttotal: $844 (4 )

Bonfield Bungalow

1 2

house , Oxford

This newly renovated Eastern Shore style guesthouse is located in Oxford, Maryland, within walking distance of the waterfront, beaches, restaurants, and shops. It has excellent user, location, and cleanliness ratings. This charming guesthouse features one bedroom and one bathroom, accommodating up to four guests. Amenities include a mini-fridge, microwave, ironing board, two bikes and helmets, and fresh linens and towels.

Saint Michaels, MD

08/07 – 08/09

$680/nighttotal: $1360 (2 )

Downtown Flat - Walk To Dining & Shops - Sleeps 4

1 2

house , Easton

This downtown Saint Michaels flat is located 10 miles from the Academy of the Arts.
This 820 square foot residence offers air conditioning, a full kitchen with a dishwasher and microwave, complimentary WiFi, and on-site parking for up to 4 guests, with an outdoor seating area and fireplace for your comfort.

10 14 reviews

Saint Michaels, MD

06/25 – 06/29

$604/nighttotal: $2416 (4 )

Cottage At Goose Neck Point

1 2

cottage , Oxford

This waterfront cottage is located on the Tred Avon River, a short drive from Easton and St. Michael’s, with easy access to local shops, restaurants, and a farmers market. It has received excellent ratings for user experience, location, and cleanliness.
The cottage has one bedroom and one bathroom, accommodating up to two guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and access to outdoor recreation equipment like bikes, a paddleboard, and kayaks.

Saint Michaels, MD

06/25 – 06/29

$972/nighttotal: $3888 (4 )

Saved By The Bay

1 2

house , Stevensville

This Stevensville house, located in Paradise Island, offers convenient access to Annapolis Harbor (23 miles), Sandy Point State Park (14 miles), and the U.S. Naval Academy (21 miles).
The 1,370-square-foot property features one bedroom, accommodates up to 13 guests, includes a private pool, free Wi-Fi, and free parking, and provides a fully equipped kitchen.

Saint Michaels, MD

06/24 – 06/28

$328/nighttotal: $1312 (4 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 3

house , Trappe

This spacious vacation home is located in Trappe, just a short drive from the Academy of the Arts and a scenic trip to Federalsburg Marina. The house offers a comfortable stay for large groups or families, with four bedrooms, three bathrooms, and a generous floor area of 2200 square feet. Enjoy the private pool, the shaded gazebo, and the fully equipped kitchen with a dishwasher and oven. Relax in the air-conditioned house with free Wi-Fi access and a flat-screen TV.

Saint Michaels, MD

06/25 – 06/29

$688/nighttotal: $2752 (4 )

Herons Roost

1 2

house , Tilghman Island

Herons Roost, a house in Mount Pleasant, is situated 18 miles from the Academy of the Arts and 68 miles from Baltimore-Washington International Airport.
This 2,230-square-foot dwelling accommodates up to 11 guests, offering complimentary Wi-Fi, an on-site kitchen, and free private parking, with a 10:00 AM check-out time.

9.9 21 reviews

Saint Michaels, MD

06/25 – 06/29

$252/nighttotal: $1008 (4 )

Charming House, Quiet Neighborhood (Entire House)

1 2

house , Easton

This Easton, Maryland house rental is located near the Chesapeake Bay, a five-minute drive from Easton's downtown area and fifteen minutes from St. Michael's.
The fully updated one-bedroom, one-bathroom home offers guests a peaceful, private acre of backyard space, complete with outdoor dining, modern appliances (including a dishwasher), air conditioning, and parking; it comfortably sleeps two.

Saint Michaels, MD

08/08 – 08/10

$770/nighttotal: $1540 (2 )

Willows Dream

1 6

house , Oxford

Willows Dream, a 1,510-square-foot house in Oxford, is located 10 miles from the Academy of the Arts and 51 miles from Salisbury-Ocean City Wicomico Regional Airport.
This Oxford vacation rental sleeps 11 guests in three bedrooms, offering two bathrooms, a full kitchen, free Wi-Fi, and free private parking.

10 1 review

Saint Michaels, MD

06/24 – 06/28

$408/nighttotal: $1632 (4 )

Relax On Kent Island In 3 Bedroom Home W/waterview

4 3

house , Stevensville

This vacation home is situated in Stevensville, offering water views and an idyllic garden setting on Kent Island, 22 miles from Annapolis Harbor and 32 miles from Baltimore - Washington International Airport.
This spacious 1490 square foot house accommodates up to 21 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, complimentary private parking, free Wi-Fi, air conditioning, and an outdoor patio for relaxation.

Saint Michaels, MD

07/31 – 08/03

$1690/nighttotal: $5070 (3 )

Spacious 6-bedroom House/cottage In Charming Royal Oak With Wifi, Ac

6 10

cottage , Oxford

This Royal Oak cottage is located a short distance from St. Michaels Winery and Windon Distilling, and offers convenient access to Saint Marys Square and Church Cove Park.
This 6-bedroom, 4-bathroom rental accommodates up to 14 guests and includes amenities such as WiFi, air conditioning, a jetted bathtub, and a washing machine, with nearby attractions including the Chesapeake Bay Maritime Museum.

Saint Michaels, MD

06/25 – 06/29

$990/nighttotal: $3960 (4 )

Sunrise Cove

1 2

house , Oxford

This Oxford, Maryland house rental, Sunrise Cove, is situated in Royal Oak, 7.8 miles from the Academy of the Arts and 31 miles from the Chesapeake Bay Exploration Center.
This 2,520-square-foot home boasts three bedrooms, two bathrooms, a private pool, Jacuzzi, free Wi-Fi, and free parking, comfortably accommodating up to 11 guests.

Saint Michaels, MD

06/27 – 07/04

$4956/nighttotal: $34692 (7 )

Tilghman Island Inn

20 4

house , Tilghman Island

This waterfront boutique inn on Tilghman Island, Maryland's Eastern Shore, offers exclusive buyouts with sweeping Chesapeake Bay views and private docks.
This inn accommodates 16 guests across 20 private rooms, featuring internet, air conditioning, a swimming pool, and 22 bathrooms, ideal for group events and offering a private, secluded retreat experience.

Find the Best Holiday Houses with Swimming Pool in Saint Michaels, MD

On-site pool access in Saint Michaels, MD makes a refreshing swim to complement your beach day a wonderful part of your daily routine.

Saint Michaels, MD

06/27 – 07/04

$925/nighttotal: $6475 (7 )

Clearview

1 2

house , Tilghman Island

Clearview, a vacation home on Tilghman Island, is located 24 miles from the Academy Art Museum and 75 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 2,060-square-foot house features three bedrooms, three bathrooms, a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and parking; it comfortably sleeps eleven guests.

Best Saint Michaels, MD houses with a kitchen

Saint Michaels, MD

07/01 – 07/05

$685/nighttotal: $2740 (4 )

Nature Retreat

1 2

house , Grasonville

This charming cottage is located in Grasonville, just a short distance from a serene duck sanctuary pond and within easy reach of the Chesapeake Bay. The peaceful environment, with a paved path winding through the property, provides a tranquil escape from the hustle and bustle of everyday life.
The two-bedroom cottage comfortably accommodates four guests. It features a spacious living room with a fireplace, an enclosed porch, and a fully equipped kitchen, making it perfect for a relaxing getaway.

10 68 reviews

Saint Michaels, MD

08/08 – 08/10

$933/nighttotal: $1866 (2 )

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

2 6

cottage , Stevensville

This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.

10 1 review

Saint Michaels, MD

07/01 – 07/05

$441/nighttotal: $1764 (4 )

Easton's Urban Oasis

1 2

house , Easton

This Easton apartment rental is centrally located, within walking distance of Four Dogs Brewing, Tiger Lily, and the Tidewater Inn, and a short drive from Oxford and St. Michaels.
The three-bedroom, one-bathroom unit sleeps six guests and includes a kitchen, air conditioning, parking, and internet access; nearby attractions include a shopping center.

Saint Michaels, MD

06/25 – 06/29

$553/nighttotal: $2212 (4 )

Crepe Myrtle

1 2

house , Tilghman Island

Crepe Myrtle, a vacation home in Tilghman, Maryland, is located 23 miles from the Maryland Institute College of Art and 74 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 1470-square-foot house features three bedrooms, two bathrooms, a full kitchen, free Wi-Fi, free parking, and accommodates up to 11 guests, offering easy access to Chesapeake Bay activities.

Frequently Asked Questions about villa rentals in Saint Michaels, MD

What is the best time to visit Saint Michaels, MD?
The best time to visit is during the spring or fall when the weather is mild and the crowds are smaller. The summer months are hot and humid, and the winter months can be chilly, but if you don't mind the cold, it's a beautiful time to see the town.
What are the best villa rentals in Saint Michaels, MD?
Among the villa rentals in Saint Michaels, MD, St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the most popular ones.
When is it easiest to book a villa rental in Saint Michaels, MD?
You'll find the best deals on villa rentals during the shoulder seasons, which are spring and fall. The summer months are the most popular time to visit, so book your villa rental early if you want to come during that time.
What are the best villa rentals with a pool in Saint Michaels, MD?
Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town, Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town are the best villa rentals with a pool in Saint Michaels, MD.
What are the top hiking trails near Saint Michaels, MD?
There aren't any hiking trails right in Saint Michaels, but if you're willing to drive a little, you can find some great hiking trails at the Blackwater National Wildlife Refuge, which is about 30 minutes away. You can also hike around the Chesapeake Bay Maritime Museum.
What are the best villa rentals with a jacuzzi in Saint Michaels, MD?
The best villa rentals with a jacuzzi in Saint Michaels, MD are Cottage On Solitude Creek - Hot Tub - Pool & Firepit, Suuri Rantahotelli - Josta On Henkeäsalpaavat Näkymät Auringonlaskuun and Minutes From Downtown St - Michael's | Game Room | Pool | Hot Tub | Pickle Ball C.
What are the advantages of renting a house or a villa in Saint Michaels, MD
Renting a house or villa gives you more space and privacy than staying in a hotel. You'll also have access to a kitchen, so you can save money by cooking your own meals. Many rentals are located right on the water, offering beautiful views and easy access to the harbor.
What are the best villa rentals for families and kids in Saint Michaels, MD?
The best villa rentals for families and kids in Saint Michaels, MD are St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Gorgeous Cottage: Easy Walk Into St Michaels Town.
Are there popular destinations near Saint Michaels, MD?
Yes, there are many popular destinations near Saint Michaels. The Eastern Shore is full of charming towns, and you can easily visit Annapolis, Baltimore, and even Washington D.C. for a day trip. The Chesapeake Bay is also a great place to explore by boat.
What are the best pet friendly villa rentals in Saint Michaels, MD?
The best pet friendly villa rentals in Saint Michaels, MD are Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town, Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town.
What are the best villa rentals with parking in Saint Michaels, MD?
St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the best villa rentals with parking in Saint Michaels, MD.

Destinations nearby

Best Saint Michaels, MD houses with air conditioning

10 3 reviews

Saint Michaels, MD

08/07 – 08/09

$352/nighttotal: $704 (2 )

#2 Egret Cottage Harris Cove

1 2

cottage , Tilghman Island

This Tilghman Island lakefront cottage, an 11-minute drive from St. Michaels Marina and the Chesapeake Bay Maritime Museum, offers tranquil waterfront views and easy water access.
This one-bedroom, one-bathroom house sleeps four and includes air conditioning, free Wi-Fi, a BBQ grill, and on-site parking; nearby attractions include the St. Michaels Museum, Avalon Theatre, Neavitt Park, and Perry Cabin Park.