Search Holiday Rentals in St. Michaels

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Find properties with these dates

Tonight
May 2 - May 3
Tomorrow
May 3 - May 4
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Top Holiday Rentals in St. Michaels

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,139
includes taxes & fees
6 May - 7 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (72)
"The house has a beautiful view of the water. Being so close to the Happy Harbor restaurant, we could order carryout & listen to the bands from the screened-in porch. It was a perfect getaway for someone who had relaxation on the mind. Thanks for sharing your lovely home."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (42)
"Great location - walkable to Downtown Annapolis and the stadium. House was very clean and has all the features and amenities you need for a comfortable stay!"
Recently Renovated Annapolis Home - Conveniently Located
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (52)
"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."
Cozy place close to the city dock
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (57)
"My wife and I stayed here for a weekend and everthing was perfect. The house looks professionally decorated and sits in a very quiet and safe neighbohhod that was fun to walk for miles. As night falls, the enchanting lights in the backyard transform the space into a serene oasis, inviting you to unwind under the stars. The addition of a hot tub and corn hole adds a playful touch, perfect for relaxation and entertainment. Our stay was nothing short of perfection. Pat and Ken were great host and...
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (77)
"A wonderfully located cottage, walking distance to quant breakfast eaterys and upscale restaurants. The sunroom was wonderful. Even tho it was still chilly outside, we did enjoy the upstairs deck and even had some wine poolside. Def recommend The Chart House Prime, just a quick walk to a restaurant with a superb wine selection and 5 Star food. Host was quick to respond to questions and very amenable to any issue we may have had. We absolutely will stay here again!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Terrace/patio
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (13)
"The location and the house were perfect. Spacious and beautiful!"
The price is £729
includes taxes & fees
6 May - 7 May
3 Story Stunner in Murray Hill <1 mile from USNA!
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Fridge, microwave, oven, stovetop
Great location, free parking
10.0 out of 10, Exceptional, (24)
"The house is in a great location near the water and close to downtown Annapolis. The house itself was perfect for our group and had everything we needed. The owner, Gibson, was very helpful and communicative and if this house was ever available again would definitely stay there."
Great location, free parking
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is £551
includes taxes & fees
8 May - 9 May
Charming Annapolis WaterVIEW Home
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is £204
includes taxes & fees
7 May - 8 May
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (194)
"Lovely setting, comfy home. Planning on staying there again."
Relaxing Waterfront Cottage Near St Michaels, Maryland
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See all available properties in St. Michaels
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

St. Michaels Holiday Rental Travel Info

Number of holiday rentals
24
Popular accommodation
St. Michaels private holiday homes
Known landmarks
St. Michaels Winery, Avalon Theatre and Academy of the Arts
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in St. Michaels you may be interested in

Premium Room | Frette Italian sheets, premium bedding, soundproofing, free WiFi
The Wildset
2.5 star property
9.8 out of 10, Exceptional, (223)
"Beautiful and friendly - great experience!"
The price is £261
includes taxes & fees
6 May - 7 May
The Wildset
Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin
5.0 star property
9.6 out of 10, Exceptional, (293)
"The room was clean and quaint. The bed was comfortable. The staff were friendly and helpful. "
The price is £578
includes taxes & fees
5 May - 6 May
Inn at Perry Cabin
Porch
Parsonage Inn
3.5 star property
9.2 out of 10, Wonderful, (119)
"The owners were great hosts"
The price is £202
includes taxes & fees
20 May - 21 May
Parsonage Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about St. Michaels holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the St. Michaels holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Michaels holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

St. Michaels holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Michaels. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Michaels holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Michaels holiday rentals we have selected for you start as low as £204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on St. Michaels rentals

At Expedia, we put the best St. Michaels holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top St. Michaels rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Michaels holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Michaels. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in St. Michaels?

Yes, there are holiday rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. The waterfront and shops are just a few reasons why tourists like St. Michaels. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that St. Michaels has to offer?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This highly rated holiday home rental in St. Michaels offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in St. Michaels?

Expedia has 33 holiday rentals for your stay in St. Michaels.

What’s there to see and do in St. Michaels?

Cultural attractions to visit include Chesapeake Bay Maritime Museum and St. Michaels Museum. St. Michaels Winery and Avalon Theatre are a couple of places you'll find in the wider area.

What’s a holiday rental in St. Michaels like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Michaels. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.

Recent reviews of St. Michaels properties
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
A verified traveller stayed at Hyatt Regency Chesapeake Bay
Posted 20 hours ago
Hyatt Regency Chesapeake Bay