Vacation rentals in Saint Michaels

Apartment in Saint Michaels

A red, two-story restaurant with a large outdoor seating area overlooks the water. Sailboats are docked nearby, and patrons can be seen dining on the patio. Surrounding foliage adds a natural element to the vibrant scene.

4.91 out of 5 average rating, 175 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

Houseboat in Kent Narrows

An inviting living space features a comfortable sofa and a wall-mounted television. A modern kitchen area includes dark cabinetry and light furnishings, while large glass doors lead to a covered deck with scenic water views. Natural light enhances the airy atmosphere.

4.97 out of 5 average rating, 150 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

5 out of 5 average rating, 117 reviews

The cottage's exterior features a spacious wooden deck with modern seating options, including a sofa and lounge chairs. Large glass doors provide an inviting view into the home, surrounded by greenery and trees. Natural light filters in, enhancing the outdoor setting.

Home in Leonardtown

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

A view from the front porch shows a quiet street with traditional homes across the road. A round wooden table is placed under the overhang, accompanied by white metal chairs. The brick pathway leads towards the tranquil surroundings, offering a welcoming setting.

5 out of 5 average rating, 102 reviews

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

4.99 out of 5 average rating, 604 reviews

A glass table holds a coffee cup and a paper bag from a local café, alongside a pastry and a muffin. Two white Adirondack chairs frame the scene, set against a backdrop of lush greenery and a garden statue.

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.

Cottage in Saint Michaels

A modern guesthouse is illuminated by soft light under a starry night sky. The silhouette of the structure is bordered by the Milky Way, creating a serene and captivating backdrop.

4.97 out of 5 average rating, 164 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Guest suite in Tilghman Island

A grassy area extends toward calm waters, where a small sailboat is visible on the shore. Wooden docks line the water's edge, leading into the distance. Soft clouds hover above, contributing to a peaceful outdoor setting.

4.97 out of 5 average rating, 146 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - 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.

Cottage in Saint Michaels

A countertop with a stainless steel sink is shown, featuring a water filtration system. The unit is clear and reveals layered filtration media. In the background, a boat-themed painting hangs above a wooden mantle, adding a coastal touch to the space.

4.98 out of 5 average rating, 237 reviews

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.

A private pool area is surrounded by lush green grass, featuring a rectangular swimming pool with clear blue water. Lounge chairs are arranged around the pool, and a shaded seating area is visible nearby, providing a relaxed outdoor environment.

4.98 out of 5 average rating, 101 reviews

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

5 out of 5 average rating, 106 reviews

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

Guest suite in Saint Michaels

An inviting loft space features two new twin beds with plush bedding accented by navy and white decor. A cozy window seat provides natural light and views, while light blue walls contribute to a serene atmosphere. The area rug adds a touch of warmth to the wooden floor.

4.78 out of 5 average rating, 358 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

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Popular amenities for Saint Michaels vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Saint Michaels

5 out of 5 average rating, 7 reviews

Historic Retreat in St. Michaels

CatherineRating, 5 stars1 week ago

This newly refurbished gem is within walking distance to Talbot Street, the heart of St. Michael’s. We enjoyed relaxing on the screened in porch before and after walking around this charming town. Dennis could not have been nicer, and is highly responsive. Would definitely recommend staying here.

5 out of 5 average rating, 17 reviews

Cottage in Oxford

Sailor's Cottage - Private Waterfront

ChristopherRating, 5 stars2 days ago

We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.

4.98 out of 5 average rating, 63 reviews

The modern guest barn is depicted against a serene river setting, framed by trees. Its large glass windows reflect the soft colors of the sunset, while the grassy lawn leads gently to the water's edge, creating a peaceful atmosphere.

Barn in Queenstown

Waterfront Modern Guest Barn

ElaineRating, 5 stars1 month ago

Overall, I enjoyed the place. The barn was minimalistic and nice for photos. The best part was the waterfront view. The house was very clean and pretty kid friendly (a few high chairs included). The kitchen had the bare minimum to cook and grill with but I wouldn’t say it was fully stocked. I would say in general that we enjoyed our stay. The kayaks were wonderful.

A charming wooden bridge leads over a small pathway, framed by lush green trees. A vintage lighthouse is visible in the distance, accompanied by a historic building. A sign indicating 'Watering Parking Only' adds to the scenic view.

5 out of 5 average rating, 10 reviews

Margaret Wells House - New

MarieRating, 5 stars5 days ago

Beautiful historic restoration in an equally beautiful area. House is comfortable, clean quiet, and spacious. Perfect location for a trip to St. Michael’s.

5 out of 5 average rating, 39 reviews

A modern kitchen features sleek white cabinetry and a minimalist design. The countertop is seamlessly integrated with a coffee maker, offering convenience for guests. Bright lighting enhances the spacious feel, while wood flooring adds a warm touch to the contemporary aesthetic.

Home in Chester

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars1 week ago

The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

4.95 out of 5 average rating, 95 reviews

A spacious two-story farmhouse with a traditional design is framed by large, leafless trees on a manicured lawn. The structure features a welcoming front porch and multiple gable roofs. Parking areas and a separate garage are visible, with a serene view of the water in the background.

Home in Chester

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars2 weeks ago

The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

5 out of 5 average rating, 35 reviews

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!

BethRating, 5 stars3 weeks ago

We had a wonderful stay in Easton. The house was perfect for our visit. Pristinely clean, comfortable, well stocked and the setting was peacefully beautiful. Everything about our stay exceeded our expectations.