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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Featured Cottages in St. Michaels

Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (175)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (117)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
On the beach, sun-loungers, beach towels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (78)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (30)
"Our family was in town to attend the promotion in the air force of a nephew at Ft. McNair. Close to everything. Beautiful house prefect for us. Enjoyed walking the boardwalk. Would highly recommend this property. Excellent communication with the host. "
North Beach Cottage - Walk to Chesapeake Bay
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (3)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (7)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Beach towels

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Wonderful. "
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Fridge, microwave, oven, stovetop

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
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.
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Other property types in St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"Nice place "
Dollhouse in Central Historic St Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (175)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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.

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between and per night for cottages in St. Michaels. No matter your budget, an excellent stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in St. Michaels?
Choose from 96 cottages in St. Michaels. No matter if you’re holidaying with the family or organising a weekend escape with your besties, Expedia can help you find the right space to reconnect with nature.
What is there to do in St. Michaels near my cottage?
After you’ve unpacked your bags and settled in, venture out and discover the cool things St. Michaels has for you to experience. St. Michaels Winery is a top attraction to add to your to-do list.