Saint Michaelsvacation rentals

From simple studios to luxe lofts, find vacation rentals that are right for you on Airbnb.

Vacation rentals in Saint Michaels

₹10172 In-Town Cottage - St Michaels!
49 reviews

Former artist loft has views of StM harbor. Across from Miles River, easy walk to Main St! Shopping, brewery, winery, restaurants await! 1st level LR/DR + pullout Queen; bright ... read more
₹25564 Avalon - Penthouse - 2 night min
24 reviews

Third floor 3 Bedroom Penthouse Flat with Harbor View and efficiency style kitchen. Private in town location with spectacular view. TV, Pool Table, Foosball in Flat. Walk to al... read more
₹6035 St Michaels Inn
14 reviews

Our quaint, pet friendly hotel in St. Michaels is a welcoming retreat for your weekend getaway, extended vacation - even a business trip. Beautifully appointed hotel rooms featu... read more
₹26107 Premier St Michaels Cottage- InTown
16 reviews

The truly special and recently restored historic Thomas Blades house is centrally located in the Town of St. Michaels. Shops, restaurants, museums and the Town park with its mag... read more
₹12545 Miles Aweigh Cottage
6 reviews

Our cottage is less than a mile from St. Michaels town center. Restaurants, shopping, Chesapeake Maritime Museum, Easton-Tilghman Island. Bike, walk or drive...our home has bee... read more
₹33905 St. Michaels 5 star waterfront/pool
7 reviews

Beautiful upscale house on the water with private pool and dock situated in a peaceful country retreat in St. Michaels, Md just 2.5 mi (short bike ride)from the center of town (... read more

Favorite Saint Michaels vacation rentals

₹12206 St. Michaels Cottage with Location!
8 reviews

The Washington Melson House is a beautiful 2 bedroom 1.5 bath cottage in the heart of St. Michaels. The house is wonderfully located on a quiet street but just a short walk to t... read more
₹12681 George Brooks Hous(URL HIDDEN)Queen
2 reviews

Historic Inn 1/2 mile outside of the town - a fabulous colonial seaport with lots of retail shops and restaurants plus the Chesapeake Bay Maritime Museum. Our inn has won two pr... read more
₹44755 Sunrise Cove
2 reviews

This little gem on the banks of Solitude Creek is a perfect family getaway! With a pool, hot tub, and canoe for exploring the creeks and tributaries of the Tred Avon River, the ... read more
₹26107 Pandion
1 review

Pandion is catered to the single family or one to two couples and just minutes to St. Michaels so you can bike or drive to town. For Weekly Reservations, please contact us for ... read more
₹16410 George Brooks House #3 King Jacuzzi
2 reviews

Historic Inn 1/2 mile outside of the town - a fabulous colonial seaport with lots of retail shops and restaurants plus the Chesapeake Bay Maritime Museum. Our inn has won two pr... read more
₹26175 Waterfront cottage in historic St. Micheals
1 review

Our place is good for couples, solo adventurers, business travelers, and families (with kids). read more

More vacation rentals in Saint Michaels

₹44755 Pines at Barrett Cove
1 review

Close in cottage with private pool, dock, fabulous outdoor patio with pizza oven and lots of other amenities. For Weekly Reservations, please contact us for a discounted rate. ... read more
₹6442 Chill in The Crib! Easton, Maryland
84 reviews

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 be... read more
₹6578 Chester Riverfront By Kent Narrows
15 reviews

My place is spacious, has great water views and is close to restaurants and dining. You’ll love it because of the bay, hot tub, pool, and outdoors space. My place is good for co... read more
₹6713 Magical Goddess Temple on the Water
7 reviews

A beautiful master suite in a spacious home overlooking the Chesapeake Bay in Maryland!!! A sacred and luxurious space with gorgeous sunset views, modern kitchen, and large bath... read more
₹16749 St. Michaels area Waterfront Home w/Deepwater Dock
4 reviews

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings... read more
₹11528 Big Sky Farm, Near Easton, MD
8 reviews

Beautiful farm property with big sky. House has 10' ceilings, heritage detailing, and big windows. Large pond on property and cottage garden. Walking distance to Triple Creek Wi... read more

Explore other destinations


Distance: 72 km


Distance: 159 km


Distance: 66 km


Distance: 76 km


Distance: 73 km


Distance: 32 km


Distance: 79 km


Distance: 722 km

West New York

Distance: 292 km

North Charleston

Distance: 741 km


Distance: 1645 km


Distance: 1309 km