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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Featured Cottages in Western Shore of Maryland

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

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

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Soul Oasis - home on the Chesapeake Bay
Sun-loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"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 AU$474
includes taxes & fees
16 Mar - 17 Mar
Soul Oasis - home on the Chesapeake Bay
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun-loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (64)
"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.
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
Hays Beach House - Hot Tub - Private Beach
Smart TV, fireplace, books

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 River Cottage for 2, dog-friendly
On the beach

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
Enchanting West River Retreat
Outdoor dining

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
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!
Chic Baltimore Retreat - 6 Mi to Downtown!
House (3 Bedrooms) | Private kitchen

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!
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!
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!
Waterfront Cottage in Piney Point w/ Kayaks!
Fridge, microwave, stovetop, dishwasher

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!
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (7)
"Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!"
The price is AU$1,103
includes taxes & fees
4 Mar - 5 Mar
Secluded Cozy Cottage in Historic Downtown
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,
2 Bedroom Cozy Beach Cottage with Beach Access
Fridge, microwave, oven, stovetop

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (12)
"This was a great little cottage and was perfect for our stay. We wanted to be close to Valey Lee and the location was great. We will definitely consider staying again."
2 Bedroom Cozy Beach Cottage with Beach Access
The Heron's Nest at Atlantic Marina
Exterior

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
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more. "
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

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

10.0 out of 10, Exceptional, (42)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is AU$504
includes taxes & fees
4 Mar - 5 Mar
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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
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
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

Fantastic 2 bedrooms apt. Harbor
Lobby

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Spectacular Penthouse at 39 west.
Lobby

Spectacular Penthouse at 39 west.

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$612
includes taxes & fees
17 Mar - 18 Mar
Spectacular Penthouse at 39 west.
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?
You can expect to pay between AU$474 and AU$1,103 per night for cottages in Western Shore of Maryland. No matter your budget, an awesome stay is just a few clicks away on Expedia. This price was 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?
You can select from 98 cottages in Western Shore of Maryland. Whether you’re travelling with the whole family, as a couple or with a group of close friends, Expedia can help you find the perfect digs.
What is there to do in Western Shore of Maryland near my cottage?
You’ll find tons of things to do in Western Shore of Maryland. If you’re headed to Washington, don’t miss National Mall, Smithsonian Institution and National Museum of African American History and Culture. Taking off to Baltimore? National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum are among the top sights here.