Search Cottages in Western Shore of Maryland

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Compare 90 Cottages in Western Shore of Maryland with updated reviews, rates, and availability.

Cozy Cottage with access to and partially obstructed views of the bay.
Exterior

Cozy Cottage with access to and partially obstructed views of the bay.

9.6 out of 10, Exceptional, (14)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (76)
"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!
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (82)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (18)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is AED 474
AED 1,059 total
includes taxes & fees
29 Dec - 30 Dec
Soul Oasis - home on the Chesapeake Bay
The Heron's Nest at Atlantic Marina
Family Room with Water View

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (286)
"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"
The Heron's Nest at Atlantic Marina
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Regularly cleaned and maintained hot tub perfect for cool nights

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
Waterfront River Cottage for 2, dog-friendly
Welcome to the waterfront cozy River Cottage!

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly
Chic Baltimore Retreat - 6 Mi to Downtown!
Exterior

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!
Secluded Cozy Cottage in Historic Downtown
Room

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (6)
"This little cottage was in an extremely convenient location. All needs within walking distance. Parking wasn’t bad - quick walk from garage. Overall would consider again!! "
The price is AED 1,377
AED 2,370 total
includes taxes & fees
7 Jan - 8 January 2025
Secluded Cozy Cottage in Historic Downtown
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Outdoor dining

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Enchanting West River Retreat
Interior

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again. "
Enchanting West River Retreat
Private Beach Front Getaway at The Sunshine Beach Cottage.
Our back patio that is just steps to the beach!

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (156)
"This was a great place to relax, have time to disconnect, and time to enjoy the company of my good friend. Loved the location and walked to the winery for a fabulous afternoon picnic. "
The Yellow Cottage on Harness Creek
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Adorable cottage with updated amenities. A great retreat for friends or a family!! "
Updated North Beach Cottage: Pet Friendly!
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living area

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is AED 411
AED 931 total
includes taxes & fees
1 Jan - 2 January 2025
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Hays Beach House - Hot Tub - Private Beach
Hays Beach House

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach
Waterfront Cottage in Piney Point w/ Kayaks!
Piney Point Vacation Rental | 3BR | 1.5BA | 2,484 Sq Ft | Stairs Required

Waterfront Cottage in Piney Point w/ Kayaks!

7.6 out of 10, Good, (4)
"First, this was a last minute booking, due to our inability to stay at our original rental. Becky was responsive to our needs so we could vacate our previous rental without delay. Next, what I loved about this property, and something you do not get very often is the amount of living, relaxing space there is in this rental. Several areas for groups of people to spread out, watch TV, look at the water, play games, often times while there are several bedrooms, there are precious few places for...
Waterfront Cottage in Piney Point w/ Kayaks!
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 Western Shore of Maryland

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino
Interior overview

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

9.6 out of 10, Exceptional, (19)
"This property meets all expectations! The host was very easy to communicate with. I loved the quaintness of the area and the ease of access to the highways was so nice! I would highly recommend this property to anyone visiting the Baltimore area!"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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 Western Shore of Maryland cost?
Cottages in Western Shore of Maryland range between AED 411 and AED 1,377 per night. These stays offer a chance to get reacquainted 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 Western Shore of Maryland?
Western Shore of Maryland has 90 cottages to choose from. Select your travel dates, enter your destination and organize your ideal vacation today.
Why book your cottage in Western Shore of Maryland with Expedia?
Reserving a cottage in Western Shore of Maryland is as easy as working out your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that come with perks like a hot tub, Expedia has something for all traveler tastes. As for unbeatable deals? We’ve got your back!
How can I find cheap cottages in Western Shore of Maryland?
The quickest way to compare cheap cottages in Western Shore of Maryland is with Expedia’s user-friendly filter tool. Tailor your search results by amenities, star rating and budget to discover unbeatable rates in just a few clicks.