A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Top Cities in Maryland

A waterfront street lined with trees and a white building with a balcony.
CottagesCottages

St. Michaels

St. Michaels

Our top choices for Maryland cottages

Deluxe Cottage | View from room

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.2 out of 10, Wonderful, (355 reviews)
"It was a very comfy vacation stay"
United States
Marlo
The price is NZ$439
includes taxes & fees
9 Aug - 10 Aug
Shore Point Cottages
Exterior

2. The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina
Pasadena
9.8 out of 10, Exceptional, (316 reviews)
"Lovely cottage on the water. The sunrise and sunsets were gorgeous. They have a pool, playground and picnic tables to enjoy. "
United States
Robert W.
The Heron's Nest at Atlantic Marina
Exterior

3. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Annapolis
9.8 out of 10, Exceptional, (44 reviews)
"Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back."
United States
Brian R.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Exterior

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

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (136 reviews)
"Lovely property with a mix of antique and contemporary comfort as well as easy and convenient access to town. Hope to be back! "
United States
Tracy M.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

5. "Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (24 reviews)
"The views are an amazing. The cottage is well appointed. The hosts were responsive. It was an excellent trip"
United States
Paul H.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

6. Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!
Chesapeake City
8.6 out of 10, Excellent, (7 reviews)
"Fantastic location "
United States
Anonymous traveller
Waterfront Cottage on the C&D Canal!
Terrace/patio

7. Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!
Deal Island Historic District
9.8 out of 10, Exceptional, (10 reviews)
"IF a Quiet, Peaceful, Beautiful place to stay is what your looking for this is the place for you."
United States
Jerry Walberg
Waterfront Maryland Retreat w/ Dock & Bay View!
Property grounds

8. Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Charlestown
10.0 out of 10, Exceptional, (19 reviews)
"Very cute and relaxing cottage. We loved it!"
United States
Kristin H.
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Property grounds

9. Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit

Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit
Oakland
10.0 out of 10, Exceptional, (48 reviews)
"Wonderful stay"
United States
Kate S.
Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit
Outdoor dining

10. Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville
9.8 out of 10, Exceptional, (70 reviews)
"The cottage is immaculate and comfortable and offers a partial view of the water from the back deck and the kitchen. A very short stroll a block down the street leads to a beautiful full view of the water, amazing sunsets, the turkey point lighthouse and soaring eagles. "
United States
cynthia k.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Exterior

11. Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fishing Creek
10.0 out of 10, Exceptional, (52 reviews)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Exterior

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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (207 reviews)
"The cottage was wonderful. Loved the historic neighborhood and the dogs loved it too! Especially the walks to the park! We’ll definitely return!"
United States
Joan B.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds

13. Beckman Peninsula Spectacular Location!

Beckman Peninsula Spectacular Location!
Swanton
9.2 out of 10, Wonderful, (180 reviews)
"Host was very easy to work with. Everything about our stay was perfect. Really enjoyed evenings in hot tub. Would definitely stay there again. Thanks"
United States
James K.
Beckman Peninsula Spectacular Location!
Exterior

14. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is NZ$536
includes taxes & fees
21 Aug - 22 Aug
Soul Oasis - home on the Chesapeake Bay
Exterior

15. Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.
Point Lookout
9.8 out of 10, Exceptional, (83 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Outdoor dining

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

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Edgewater
10.0 out of 10, Exceptional, (230 reviews)
"Awesome location and very nice, we had a great stay! "
United States
Megan B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

17. Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay
Perryville
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful sunrises. Quiet spot on the water. Enjoyed the area and being close to Havre de Grace and Aberdeen. "
United States
Rachel M.
Charming Cottage - Northeast River / Chesapeake Bay
Exterior

18. Private Home in Garrett County, surrounded by trees, fields and farmland.

Private Home in Garrett County, surrounded by trees, fields and farmland.
Grantsville
10.0 out of 10, Exceptional, (54 reviews)
"Awesome house. And great location "
United States
Richard M.
The price is NZ$423
includes taxes & fees
21 Aug - 22 Aug
Private Home in Garrett County, surrounded by trees, fields and farmland.
Exterior

19. Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (51 reviews)
"Great accomodations!"
United States
Linda S.
The price is NZ$755
includes taxes & fees
2 Sept - 3 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague
Terrace/patio

20. Cozy Home w/ Theater, Hot Tub, Mtn Views

Cozy Home w/ Theater, Hot Tub, Mtn Views
McHenry
9.8 out of 10, Exceptional, (39 reviews)
"Very cozy place to stay, will be staying again!"
United States
Hannah F.
Cozy Home w/ Theater, Hot Tub, Mtn Views
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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Top Maryland Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Nice"
Dustin 1-night trip
Posted 5 hours ago
Princess Royale Oceanfront Resort

Find out more about Maryland

Maryland Cottages information

Number of reviews
1,621
Accommodation
455 Cottages
Lowest Price
NZ$423
Highest Price
NZ$755

Frequently asked questions

How much do cottages in Maryland cost?
Cottages in Maryland range between NZ$423 and NZ$755 per night. These stays offer a chance to touch base with nature — at a price you can afford. 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 Maryland?
Look up our 455 cottages in Maryland and reserve your favourite. Whether you're embarking on a holiday with the fam or a weekend with pals, your ideal stay is just a few clicks away with Expedia.
What is there to do in Maryland near my cottage?
Whether you enjoy food, shopping, history or sightseeing, Maryland is one place where it's difficult to be bored! The top city of Washington has loads of things to do and see, including Arlington House-The Robert E. Lee Memorial, Cady's Alley and Francis Scott Key Memorial Park. If you're staying in Baltimore, Geppi's Entertainment Museum, Union Soldiers and Sailors Monument and Edgar Allan Poe's Gravesite and Memorial should be on your to-do list.

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