Search Cottages in Western Shore of Maryland

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
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19 Dec - 21 Dec
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16 Jan - 18 Jan

Cottages in Western Shore of Maryland

The Heron's Nest at Atlantic Marina
Terrace/patio

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (305)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Exterior

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (122)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is SAR 1,350
SAR 2,493 total
includes taxes & fees
24 Sep - 25 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (36)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
House (3 Bedrooms) | Interior

Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!

3.0 star property
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Outdoor dining

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

10.0 out of 10, Exceptional, (218)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (14)
"We had a very lovely stay . This is an excellent location . "
The price is SAR 1,875
SAR 3,053 total
includes taxes & fees
19 Oct - 20 Oct
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (167)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek
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, (51)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Exterior

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

10.0 out of 10, Exceptional, (96)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Exterior

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Piney Point, private , Beach Front Cottage
On the beach

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (91)
"Wonderful hosts, beautiful property! Already planning next years visit! "
Piney Point, private , Beach Front Cottage
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Outdoor dining

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

10.0 out of 10, Exceptional, (18)
"The house was very nice and had great amenities supplied by the owners. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.
Waterfront River Cottage for 2, dog-friendly
Property grounds

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"Great little spot in a private location but close to everything. Super clean and comfy!"
Waterfront River Cottage for 2, dog-friendly
The Cottage at Merryland Farm
Exterior

The Cottage at Merryland Farm

10.0 out of 10, Exceptional, (3)
"A lovely countryside spot amidst friendly horses in a well sized and fitted out cottage. Can highly recommend for a getaway or occasion. "
The Cottage at Merryland Farm
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, (30)
"Perfect location, we were in town for birthdays and a wedding shower. Short drive to our favorite spots, Two Rivers, Primos & Seaside for steamed crabs. House has everything you need. Will return on our future visits to the Dena. "
House w/Water Views of Rock Creek 2BA 2BA Cottage
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!
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Exterior

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (54)
"The property was very clean and well decorated. You could tell care and love is placed into the house and landscaping. The backyard and pool area is gorgeous! Despite unlucky/rainy weather and temperatures in the 60s, the pool was heated so warm that we went in everyday with the kids which was so nice. Annapolis is very close by. Plenty of fluffy towels, comfortable beds, nice small touches of welcome goodies and quality soap/shampoo, etc."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
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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Top Western Shore of Maryland Hotel Reviews

Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

10/10 Excellent
"Fabulous "
Michael 1-night trip
Posted 10 hours ago
Hyatt Regency Baltimore Inner Harbor

Frequently asked questions

How much do cottages in Western Shore of Maryland cost?
Prepare to pay between SAR 2,493 and SAR 3,053 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 127 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia