Cottages in Maryland
183 properties for Cottages. Compare and book at the best price!
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Popular Cottages in Maryland
Garrett County, Deep Creek Lake
8.5
Cottage for 10 people, with hot tub and terrace
Free cancellation
from $306 per night
Garrett County, Deep Creek Lake
9.3
Cottage for 8 people, with pool and hot tub as well as balcony
from $363 per night
Garrett County, Maryland
9.4
Cottage for 5 people, with balcony
Free cancellation
from $246 per night
Garrett County, Deep Creek Lake
9.9
Cottage for 8 people, with pool and hot tub, with pets
from $369 per night
St. Michaels, Chesapeake Bay
10.0
Cottage for 4 people, with yard, with pets
Free cancellation
from $618 per night
Garrett County, Deep Creek Lake
9.6
Cottage for 4 people, with hot tub and balcony
from $343 per night
Garrett County, Deep Creek Lake
9.8
Cottage for 6 people, with hot tub and balcony, with pets
from $338 per night
Southern Maryland, Maryland
9.8
Cottage for 8 people, with yard, with pets
Free cancellation
from $194 per night
Garrett County, Maryland
10.0
Cottage for 12 people, with terrace and hot tub
Free cancellation
from $365 per night
Rockville, Maryland
9.8
Cottage for 6 people, with yard and terrace, with pets
Free cancellation
from $245 per night
Southern Maryland, Maryland
9.9
Cottage for 12 people, with yard
Free cancellation
from $818 per night
Chesapeake Bay, Maryland
10.0
Cottage for 8 people, with yard
Free cancellation
from $279 per night
Deal Island, Chesapeake Bay
9.3
Cottage for 8 people, with hot tub and terrace as well as yard, with pets
Free cancellation
from $129 per night
Chesapeake Bay, Maryland
9.7
Cottage for 3 people, with yard
Free cancellation
from $168 per night
Ocean Pines, Worcester County
9.6
Cottage for 6 people, with terrace
Free cancellation
from $199 per night
Chesapeake Bay, Maryland
10.0
Cottage for 5 people, with yard and terrace
Free cancellation
from $295 per night
Chesapeake Bay, Maryland
9.7
Cottage for 4 people, with yard and terrace
Free cancellation
from $342 per night
Southern Maryland, Maryland
10.0
Cottage for 7 people, with terrace and yard
Free cancellation
from $290 per night
Southern Maryland, Maryland
9.7
Cottage for 4 people, with balcony, with pets
Free cancellation
from $377 per night
St. Michaels, Chesapeake Bay
9.7
Cottage for 5 people, with yard and pool as well as terrace
Free cancellation
from $338 per night
Garrett County, Maryland
9.7
Cottage for 4 people, with terrace and yard
Free cancellation
from $271 per night
Southern Maryland, Maryland
9.9
Cottage for 8 people, with yard
Free cancellation
from $433 per night
Blue Ridge Mountains, Maryland
9.9
Cottage for 8 people, with terrace
Free cancellation
from $280 per night
Chesapeake Bay, Maryland
9.9
Lodge for 12 people, with yard
from $889 per night
Find Cottages in Maryland
Best Cottages in Maryland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Garrett County, Maryland
Cottage • 3961 ft² • 4 Bedrooms
Garrett County, Maryland
8.5
Tall Oaks Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Savor your next mountain escape in the pleasant and secluded neighborhood of Tall Oaks Retreat! This beautifully updated home offers a perfect balance of comfort and nature. With an open floor plan, skylights, and two inviting fireplaces—one gas and one wood-burning—this bright and spacious retreat sets the stage for a relaxing mountain getaway. The main level features two expansive living areas, one with a stunning floor-to-ceiling r...
from $313 / night
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Annapolis, Chesapeake Bay
Cottage • 700 ft² • 1 Bedroom
Annapolis, Chesapeake Bay
10.0
(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again. The cottage is all yours, and its self check-in, but please reach out on the app or on Jim's cell for anything at all! Check-in: After 4:00 PM (early check-in when available) Check-out: 11:00 AM (late...
from $388 / night
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Chesapeake Bay, Maryland
Cottage • 9 Guests • 3 Bedrooms
Chesapeake Bay, Maryland
9.8
This charming private waterfront cottage on 7 private acres sits on Marylands beautiful Eastern Shore. Cedar Point cottage is packed with modern amenities and charm. Waterfront Pool, Hot tub, Dock with boat slip, water and electric; kayaks, Stand up paddle boards, wood burning fireplace & outdoor fire pit with firewood supplied, tv's in each bedroom, A/C, covered deck with grill and arbor, dvd with large selection of movies, Smart TV's, DISH entertainment system, sandy beach, Hammocks, crab traps.
from $1,094 / night
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Other holiday ideas and property types in Maryland that might be interesting
FAQs: Cottages in Maryland
Which types of services can you expect to find at the cottages in Maryland?
Out of the facilities available on Holidu, it seems that the cottages in Maryland have everything that vacationers wish for! Here, the cottages generally include a variety of amenities, the most popular being: air-conditioning (92%), internet (89%), and barbecue (75%)...Are you convinced yet?
How are the reviews for the cottages in Maryland?
The cottages in this destination are often well reviewed. Many (62%) have a rating of 4.5 stars, which suggests that here, you can easily find the perfect cottage for your next vacation!
Are the cottages in Maryland suitable for family vacations?
Judging by the Holidu database, 59% of cottages in Maryland are child-friendly, it should therefore be very easy for you to find the ideal cottage for you and your children.
Are the cottages in Maryland suitable for travelers who wish to take their pets on vacation?
Certainly! In Maryland, 42% of the cottages welcome them with open arms, 54% even have a garden!
Do the cottages in Maryland tend to come with Wi-Fi?
Certainly! According to Holidu, 89% of cottages in Maryland have internet connection. You will be able to stay connected during your stay!
Do the cottages in Maryland usually have a fireplace or a pool?
Good news! According to Holidu, the cottages in Maryland have everything you need for all seasons. Here, 43% have a fireplace and 12% a pool.
Are the cottages in Maryland suitable for trips with several people or rather for a weekend break as a small group?
Here, according to Holidu, 40% of cottages welcome up to eight people, 16% of these cottages are made up of at least four bedrooms. But 92% of cottages are also perfect for families of up to four people, 82% of the cottages are made up of at least two separate bedrooms. This is therefore the perfect destination for big and small families alike!
Do the cottages in Maryland have a beautiful view?
15% of cottages have a balcony or terrace, and 50% have a view, but since it is not very common so availability can be limited. If this is important to you, you should anticipate a bit more time for research, and use the filters to be sure to find the cottage of your dreams. However, 54% of cottages in Maryland have gardens, where you can bask in the sun. If you like to have lunch or dinner outside, and especially if you like barbecues, 75% of the cottages have them.