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Vacation rentals in St. Michaels

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Quick stats about vacation rentals in St. Michaels

  • Total vacation rentals

    Explore 40 vacation rentals in St. Michaels

  • Nightly prices starting at

    St. Michaels vacation rentals start at €198 per night before taxes and fees

  • Verified guest reviews

    Over 3,270 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of St. Michaels vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across St. Michaels rentals

  • 4.9 Average rating

    St. Michaels stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in St. Michaels

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

4.98 out of 5 average rating, 200 reviews
Top guest favorite
The living room features a chandelier, a decorative mirror above the fireplace, and a cozy seating area with two armchairs and a chaise lounge. A colorful area rug covers the floor, while a small table and lamp provide additional lighting.
Home in St. Michaels

Historic Berkeley Hall in the heart of town

Berkeley hall is centrally located in historic Saint Michaels. Park your car and walk to everything! Great shops, restaurants and 3 blocks to the water. First floor includes a high ceiling parlor that connects to a lovely side porch and large kitchen. There is a mahogany staircase that takes you to the 2nd floor that has 2 master suites. One has a king bed the other has a queen bed w/ ladder to loft which is best for kids -has a twin size futon sofa bed. Perfect home for a romantic getaway.

4.96 out of 5 average rating, 217 reviews
Top guest favorite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.99 out of 5 average rating, 149 reviews
Top guest favorite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.99 out of 5 average rating, 657 reviews
Top guest favorite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

4.99 out of 5 average rating, 224 reviews
Guest favorite
A vibrant navy sofa decorated with red and white cushions sits in front of a glossy black coffee table. A geometric rug covers the wooden flooring, while a decorative plant and a luminous wall create a welcoming atmosphere. A series of signs indicating local towns provide a charming touch.
Apartment in St. Michaels

Charming Apt. in St. Michaels

Welcome to Lucky Duck II! Enjoy a renovated, two-story private apartment in the heart of St. Michaels, located on Talbot Street in the historic 1850s McMillan House. Our cozy British-inspired retreat sleeps 4 with a private queen bedroom and full bath upstairs, plus a sleeper sofa and half bath downstairs. Enjoy a kitchenette, bar area, free WiFi & YouTube TV. Best of all, you're steps from the Miles River, restaurants, shops, museums & everything St. Michaels has to offer!

4.96 out of 5 average rating, 100 reviews
Top guest favorite
A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.
Apartment in St. Michaels

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

4.98 out of 5 average rating, 160 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 reviews
Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 364 reviews
Top guest favorite
A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.
Cottage in St. Michaels

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

4.97 out of 5 average rating, 301 reviews
Top guest favorite
A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.
Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

5.0 out of 5 average rating, 125 reviews
Top guest favorite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

4.99 out of 5 average rating, 139 reviews

Popular amenities for Saint Michaels vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near St. Michaels's top sights

Chesapeake Bay Maritime Museum

61 locals recommend

Eastern Shore Brewing

16 locals recommend

Sail Selina II

11 locals recommend

Village Shoppe

9 locals recommend

Inn at Perry Cabin

6 locals recommend

Chesapeake Bay Outfitters

4 locals recommend

House rentals in Saint Michaels

Top guest favorite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

4.97 out of 5 average rating, 110 reviews
Guest favorite
A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.
Home in St. Michaels

SM's Premier Rental Heated Pool (closes 10/27)

4.97 out of 5 average rating, 116 reviews
Guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

4.95 out of 5 average rating, 310 reviews
Guest favorite
Lush green grass leads to the waterfront, where the calm water reflects the surroundings. Two white Adirondack chairs sit invitingly under the shade of tall trees, providing a serene spot for relaxation. A wooden dock extends into the water, enhancing the picturesque setting.
Home in Neavitt

Waterfront, Dog friendly, St Michaels home

4.94 out of 5 average rating, 106 reviews
Guest favorite
A classic historic cottage features white siding and a steeply pitched roof. An American flag hangs from the front door, which is framed by a small porch and decorative elements. Lush greenery and a white picket fence enhance the welcoming facade.
Home in St. Michaels

Premier St Michaels Cottage- In Town Location

4.87 out of 5 average rating, 141 reviews
Top guest favorite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

5.0 out of 5 average rating, 186 reviews
Top guest favorite
A small historic home is shown from the front, featuring light beige siding and white trim. A welcoming porch with potted plants is visible, alongside two chairs and a table. The door is painted in a soft blue, framed by large windows on the upper floor.
Home in St. Michaels

Small Historic House Downtown St Michaels

4.89 out of 5 average rating, 237 reviews
Top guest favorite
The historic home features a charming blue exterior with white accents, situated behind a low picket fence. An American flag is displayed at the front. Surrounding greenery enhances the welcoming appearance, while neighboring homes can be seen in the background.
Home in St. Michaels

Ahoy St. Michaels! - A Historic Retreat

5.0 out of 5 average rating, 61 reviews

Other great vacation rentals in St. Michaels

Guest favorite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

4.92 out of 5 average rating, 267 reviews
Guest favorite
Home in Wittman

Waterfront cottage in Wittman Maryland

4.95 out of 5 average rating, 22 reviews
Guest favorite
Apartment in St. Michaels

Downtown St. Michaels | Porch + Pet-Friendly

4.96 out of 5 average rating, 25 reviews
Top guest favorite
A serene waterfront scene features three colorful paddleboards laid on a grassy area, with several Adirondack chairs arranged in front of the tranquil water. The sky is bright and clear, enhancing the natural beauty of the setting.
Home in Easton

Arcadia Shores On The Cove

4.95 out of 5 average rating, 19 reviews
Top guest favorite
The exterior of a two-story house features light-colored siding and contrasting red shutters. A covered front porch with two chairs invites relaxation, while a landscaped yard with greenery and stone borders enhances the outdoor space. The surrounding trees provide privacy and tranquility.
Home in St. Michaels

Private&Cozy/3br+2ba/1mi to town

4.94 out of 5 average rating, 88 reviews
Top guest favorite
An elevated view of a green two-story house is surrounded by tall trees, with water visible in the background. The layout includes a wraparound porch and landscaped shrubbery, leading to a winding drive that approaches the front entrance.
Guesthouse in St. Michaels

Secluded water, private sitting room, full bath!

5.0 out of 5 average rating, 45 reviews
Top guest favorite
Cottage in St. Michaels

Lovely Waterfront Cottage on 2 acres, St. Michaels

4.97 out of 5 average rating, 35 reviews
Top guest favorite
Four white Adirondack chairs are positioned in a grassy area, facing a serene pond. The surrounding landscape features tall trees and lush greenery, providing a tranquil natural setting. Bright sunlight enhances the peaceful atmosphere of the outdoor space.
Home in Easton

Eastern Shore Retreat!

5.0 out of 5 average rating, 57 reviews

When is the best time to visit St. Michaels?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€217€218€232€248€265€265€244€241€248€250€238€238
Avg. temp3°C4°C8°C14°C19°C24°C26°C25°C22°C16°C10°C5°C

Frequently Asked Questions

  • What are the best places to stay in Saint Michaels?

    Many travelers choose lodgings around the waterfront or historic downtown for easy access to shops, restaurants, and parks. Family-friendly homes, cozy cottages, and pet-welcoming stays are available throughout Saint Michaels.

  • What are the best things to do in Saint Michaels with kids?

    Visit interactive exhibits at the Chesapeake Bay Maritime Museum, play in local parks, and enjoy ice cream shops along the main street. Kids often enjoy joining boat tours and seasonal craft workshops around town.

  • What are some of the best things to do in Saint Michaels?

    Explore maritime history at the Chesapeake Bay Maritime Museum, stroll the historic district, or enjoy boat tours on the bay. The town has galleries, parks, and seasonal activities that invite visitors to connect with local traditions.

  • How is the weather in Saint Michaels?

    Saint Michaels has cool winters around 29–45°F (-1–7°C), and warm, humid summers near 87°F (31°C). Spring and autumn bring mild temperatures, making outdoor exploration comfortable for most travelers.

  • When is the best time to visit Saint Michaels?

    Late spring through early fall is often recommended for milder temperatures, outdoor festivals, and scenic boat tours. Winter brings quieter streets and cool weather around 29–45°F (-1–7°C), while summer sees warmer afternoons near 87°F (31°C).

  • What are the best places to visit in Saint Michaels?

    Frequently suggested spots include the Chesapeake Bay Maritime Museum, the historic downtown, and waterfront parks. Saint Michaels also has unique shops and galleries rooted in local traditions.

  • What are some hiking trails in Saint Michaels?

    Saint Michaels has walking and biking trails around parks and the waterfront, with gentle paths suitable for most abilities. For more nature experiences, explore trails in nearby nature preserves and wooded areas.

  • What are some family activities we can do in Saint Michaels?

    Families often explore interactive exhibits at the Chesapeake Bay Maritime Museum, stroll through waterfront parks, and join boat tours. Local ice cream shops and art workshops provide engaging options for children and adults.

  • What are some of the best day trip ideas from Saint Michaels?

    Explore neighboring waterfront towns, nature preserves, and historic sites around the Eastern Shore. Outdoor lovers can visit wildlife sanctuaries or plan an outing to scenic trails and cultural museums nearby.

  • Are there any pet friendly accommodations available in Saint Michaels?

    Saint Michaels has accommodations that welcome pets, particularly around the waterfront and historic district. Parks and trails make it easy to spend time outdoors with your dog.

  • What are some local tips for visiting Saint Michaels?

    Explore the town’s walkable streets, and take time to visit local art galleries and independent shops. The waterfront is often recommended for its scenic views, and packing layers is helpful since weather changes seasonally.

  • What is Saint Michaels known for?

    Saint Michaels has a maritime heritage, charming historic buildings, and a vibrant waterfront lined with shops and restaurants. The town is frequently suggested for its boating culture and welcoming community atmosphere.

  • What are the best hidden gems to explore in Saint Michaels?

    Wander smaller art galleries, discover locally owned bakeries, and keep an eye out for unexpected garden spaces around town. The historic district has lesser-known nooks perfect for exploring and connecting with local culture.

  • What are the best foods to try in Saint Michaels?

    Local flavors often feature Maryland blue crab, oyster dishes, and traditional seafood soups. Saint Michaels also has bakeries known for locally inspired pastries and restaurants serving seasonal produce.

  • What should I bring for a trip to Saint Michaels?

    Pack layers to adapt to seasonal weather, especially for cool evenings and rainy days. Comfortable walking shoes, a light rain jacket, and sun protection are often helpful for exploring parks, waterfront areas, and historic streets.

  • What is the nightlife in Saint Michaels like?

    Nightlife in Saint Michaels centers around casual waterfront venues, local pubs, and restaurants hosting live music and seasonal events. Most evenings are relaxed, with options for social dining and community gatherings.

  • What are the most popular events or festivals in Saint Michaels?

    Saint Michaels hosts maritime-themed festivals, arts fairs, and seasonal celebrations, often suggested during late spring and autumn. Many travelers look forward to food and wine events, outdoor concerts, and holiday-themed gatherings.

  • Are there family friendly vacation rentals in Saint Michaels?

    Saint Michaels has a range of vacation rentals suitable for families, including homes with larger kitchens and outdoor spaces around the historic town and waterfront areas. Many properties welcome children and provide easy access to parks.

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