Search Cottages in Western Shore of Maryland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 120 Cottages in Western Shore of Maryland with updated reviews, rates, and availability.

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (21)
"Perfect family get away with a great view!"
The price is SAR 454
SAR 1,034 total
includes taxes & fees
28 Apr - 29 Apr
Soul Oasis - home on the Chesapeake Bay

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (65)
"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.

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"We throughly enjoyed our stay at Hays Beach. Tim was responsive and incredibly helpful as we were planning our visit. The house is beautifully appointed - from the furnishings to the outdoor equipment. We were also impressed with all the included basic details that made our stay so much more comfortable. We would definitely choose to stay here again!"
Hays Beach House - Hot Tub - Private Beach

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

9.2 out of 10, Wonderful, (19)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (14)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Beach Access

Easter and Spring Break Available: The Hideaway in Hays Beach - Chesapeake Bay

10.0 out of 10, Exceptional, (113)
"A wonderful place to just relax. We loved being able to walk on the beach as well as just sit in the backyard relaxing and chatting! House is clean and well-stocked and had different areas for gathering! "
Easter and Spring Break Available: The Hideaway in Hays Beach - Chesapeake Bay

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

9.6 out of 10, Exceptional, (4)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is SAR 536
SAR 1,247 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"Really like this place "
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

9.8 out of 10, Exceptional, (10)
"Everything we needed, relaxing visit"
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

10.0 out of 10, Exceptional, (24)
"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

Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

10.0 out of 10, Exceptional, (80)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"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,

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (287)
"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"
The Heron's Nest at Atlantic Marina

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (14)
"We had a very nice time at this house. The neighborhood was very nice to walk in and we enjoyed watching the Bay."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (31)
"The place was wonderful, clean and well stocked. It was a great place to stay - kudos to the hosts for an inviting atmosphere."
North Beach Cottage - Walk to Chesapeake Bay

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

10.0 out of 10, Exceptional, (86)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

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

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"Great property right outside of north beach"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
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.
Don't see what you're looking for?
See all available properties in Western Shore of Maryland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Western Shore of Maryland

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.

9.4 out of 10, Exceptional, (23)
"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.

One bedroom at Baltimore Covention Ctr

4.0 star property
One bedroom at Baltimore Covention Ctr
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.