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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Browse Select Western Shore of Maryland Cottages

The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (292)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
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, (211)
"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
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (36)
"The house was beautiful and comfortable. It had everything you could need even though we were out and about all the time. Would definitely return."
North Beach Cottage - Walk to Chesapeake Bay
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Fridge, microwave, oven, stovetop

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (47)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (12)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is £601
includes taxes & fees
6 Jul - 7 Jul
Secluded Cozy Cottage in Historic Downtown
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
On the beach, sun-loungers, beach towels

Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly

10.0 out of 10, Exceptional, (32)
"Really like this place "
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
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, (27)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Rock Creek Cottage, Waterfront, Serene Views
Fridge, microwave, oven, stovetop

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
Perfect location for USNA Commissioning Week
View from property

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (83)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (28)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Walk to Everything - Historic Art’s District
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District
Chic Baltimore Retreat - 6 Mi to Downtown!
House (3 Bedrooms) | Front of property

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!
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!
New Property! Escape to Downtown Annapolis Murray Hill Home with Luxe King Suite and Porch Vibes
Fridge, microwave, oven, stovetop

New Property! Escape to Downtown Annapolis Murray Hill Home with Luxe King Suite and Porch Vibes

New Property! Escape to Downtown Annapolis Murray Hill Home with Luxe King Suite and Porch Vibes
Soul Oasis - home on the Chesapeake Bay
Sun-loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (29)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is £194
includes taxes & fees
8 Jul - 9 Jul
Soul Oasis - home on the Chesapeake Bay
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (16)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (90)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Exterior

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

9.0 out of 10, Wonderful, (4)
"The location was perfect; you can walk to the beach, stores, restaurants! Chesapeake Beach looks like a scene from Gilmore Girls! 15 minutes from a larger town with more options. 40 minute scenic drive to Annapolis or D. C. The house is small but perfect for 2 people! Be aware that the master bed is a standard size, but the second bedroom has a daybed and pull out bed! The back yard has some insecure spots if you bring a pet, but we used sections of our pet pen to cover those. And no dishwasher,...
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
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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Frequently asked questions

How much do cottages in Western Shore of Maryland cost?
Prepare to pay between £194 and £601 per night for cottages in Western Shore of Maryland. No matter your budget, a wonderful stay is just 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 Western Shore of Maryland?
Western Shore of Maryland has 118 cottages to choose from. Click on your travel dates, enter your destination and plan your perfect trip today.
Why book your cottage in Western Shore of Maryland with Expedia?
Booking a cottage in Western Shore of Maryland is as easy as working out your travel dates and picking your ideal place for outdoor recreation and relaxation. From upmarket retreats to low-cost stays and cottages that come with amenities like a kitchenette, Expedia has something for all tastes and styles. As for irresistible deals? We've got them too!