St. Michaels Vacation Rentals from SAR 337: Search Short-Term Rentals

A lighthouse on stilts with a green roof, surrounded by water and greenery.

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Our top choices for St. Michaels vacation rentals

1. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

Easton

Lynn G.

SAR 1,508 total

includes taxes & fees

16 Nov - 17 Nov

A deck with a view of a marina, including boats and docks.

2. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

A lighthouse with a white exterior, a balcony, and a metal roof.

3. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

SAR 1,232 total

includes taxes & fees

23 Nov - 24 Nov

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

4. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

SAR 1,091 total

includes taxes & fees

15 Nov - 16 Nov

A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

SAR 1,211 total

includes taxes & fees

24 Nov - 25 Nov

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

6. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

SAR 1,166 total

includes taxes & fees

24 Nov - 25 Nov

7. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

SAR 1,179 total

includes taxes & fees

13 Dec - 14 Dec

A house with a yellow door and a window with a lamp outside.

8. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

9. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Mary Beth S.

SAR 1,400 total

includes taxes & fees

13 Dec - 14 Dec

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

10. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

SAR 1,198 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

11. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

SAR 1,166 total

includes taxes & fees

13 Dec - 14 Dec

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

12. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

SAR 975 total

includes taxes & fees

13 Dec - 14 Dec

A two-story house with a red roof, a brick chimney, and a small porch.

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveler

SAR 3,759 total

includes taxes & fees

13 Nov - 14 Nov

A park with cherry blossom trees, a grassy area, and a pathway.

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

Sam C.

SAR 4,651 total

includes taxes & fees

1 Dec - 2 Dec

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

15. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

SAR 1,860 total

includes taxes & fees

16 Nov - 17 Nov

A beach with chairs and a pier in the background.

16. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

SAR 1,771 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

17. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

SAR 1,635 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

18. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

SAR 907 total

includes taxes & fees

16 Nov - 17 Nov

A marina with boats docked, a water tower, and residential buildings with balconies.

19. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Cambridge

mike

SAR 1,698 total

includes taxes & fees

13 Nov - 14 Nov

20. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

SAR 1,392 total

includes taxes & fees

13 Dec - 14 Dec

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Find vacation rentals that suit your style

Top St. Michaels Hotel Reviews

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

The Oaks Waterfront

Easton

10/10 Excellent

William

A large, two-story house with a prominent tower and a covered porch.

Hummingbird Inn

Easton

10/10 Excellent

My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...

Robert

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

Marvel's on the Creek

East New Market

10/10 Excellent

This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...

Joseph

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

Sandaway Suites & Beach

Oxford

10/10 Excellent

joseph

A white two-story building with a central entrance, a staircase, and a small garden area.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Excellent

MARA

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A hot tub in a grassy area with a building in the background.

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A modern kitchen with a large island, bar stools, and a wine rack.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Laurel Grove Inn on the South

Annapolis

10/10 Excellent

Marti

A waterfront property with a covered patio, a dock, and a boat.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

Frequently Asked Questions

Are there vacation rentals in St. Michaels?

Yes, we have vacation rentals in St. Michaels close to Chesapeake Bay Maritime Museum, or you can choose 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 vacation rentals in St. Michaels?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: You might want to consider this vacation home rental near St. Michaels, which is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in St. Michaels?

Expedia has 35 vacation rentals for your stay in St. Michaels.

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

Cultural attractions include Chesapeake Bay Maritime Museum and St. Michaels Museum, whereas Church Cove Park and CL Open Field are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Saint Michaels Town Hall and St. Michaels Marina.

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

Vacation rentals are private properties where you can stay for short or long periods in St. Michaels. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.

St. Michaels Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Michaels vacation rentals

1. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

2. Cass-N-Reel Luxury Houseboat

3. Charming Coastal/Country Home w/3 Acres & Sauna!

4. Relax on Kent Island in 4 Bedroom Home w/Waterview

5. Cambridge Apt in Walkable Neighborhood

6. Family Friendly Cozy 3 Bedroom Duplex

7. Cambridge Apt in Walkable Neighborhood

8. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

9. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10. Beachside Oasis with Beach Passes & King Suite by A Haven Away

11. The Cozy Crab- Your Charming Haven in Lovely North Beach!

12. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

15. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

16. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

17. Sunset Cottage - West River Access and Views!

18. Sailwinds Loft at Cambridge Creek

19. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

20. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Find vacation rentals that suit your style

Top St. Michaels Hotel Reviews

The Oaks Waterfront

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in St. Michaels?

What are some of the best vacation rentals in St. Michaels?

How many vacation rentals are there in St. Michaels?

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

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

15. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8