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Check prices for these dates

In two weeks
12 June - 14 June
In two months
24 July - 26 July
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Western Shore of Maryland cottages

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (49 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is AU$418
includes taxes & fees
26 May - 27 May
Soul Oasis - home on the Chesapeake Bay
Property grounds

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

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (50 reviews)
"We love this place!"
United States
Joan K.
The price is AU$459
includes taxes & fees
27 May - 28 May
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (14 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is AU$531
includes taxes & fees
26 May - 27 May
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
House (3 Bedrooms) | Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is AU$651
includes taxes & fees
4 June - 5 June
Idyllic Pasadena Retreat With Garden + Hot Tub!
Exterior

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is AU$507
includes taxes & fees
26 May - 27 May
Cottage Located on the Patuxent River!
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is AU$1,862
includes taxes & fees
28 May - 29 May
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$931
includes taxes & fees
26 May - 27 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AU$1,048
includes taxes & fees
26 May - 27 May
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
House (2 Bedrooms) | Interior

Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market
3.0 star property
York
The price is AU$546
includes taxes & fees
26 May - 27 May
Work & Play! Home 1 Mi to Dtwn & Central Market
Outdoor spa tub

Restful and Quaint Cottage

Restful and Quaint Cottage
Conestoga
9.8 out of 10, Exceptional, (132 reviews)
"It was so peaceful and had plenty of room for me and my friends to have my bachelorette weekend! Everything was so cute and easily accessible!"
United States
Emily S.
The price is AU$386
includes taxes & fees
1 June - 2 June
Restful and Quaint Cottage
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is AU$376
includes taxes & fees
27 May - 28 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AU$300
includes taxes & fees
1 June - 2 June
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Property grounds

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.0 out of 10, Wonderful, (4 reviews)
"Great location in downtown Hanover within walking distance of the square where there are various shops and dining options. "
United States
Danna W.
The price is AU$396
includes taxes & fees
30 May - 31 May
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is AU$721
includes taxes & fees
27 May - 28 May
Thunder Hill Retreat - Spacious/Deck/Hot tub
Terrace/patio

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is AU$685
includes taxes & fees
27 May - 28 May
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$378
includes taxes & fees
27 May - 28 May
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AU$588
includes taxes & fees
27 May - 28 May
2 Bedroom Cottage at Coles Point Marina
House (3 Bedrooms) | Interior

Pets Welcome: Quiet Silver Spring Retreat!

Pets Welcome: Quiet Silver Spring Retreat!
3.0 star property
Silver Spring
The price is AU$645
includes taxes & fees
22 June - 23 June
Pets Welcome: Quiet Silver Spring Retreat!
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
'the Bayside Escape' Remote Chesapeake Bay Estate
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Had a wonderful weekend stay at the DoubleTree! The hotel was clean, comfortable, and the staff was warm and welcoming from check-in to check-out. One of the best parts was the convenient location close to the entertainment venue, which made our evening stress-free and enjoyable. The beds were cozy, the atmosphere was relaxing, and the famous warm cookies were a nice touch. I would definitely stay here again for another weekend getaway!"
TERESA 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Western Shore of Maryland

Western Shore of Maryland Cottages information

Number of reviews
399
Accommodation
116 Cottages
Lowest Price
AU$300
Highest Price
AU$1,862

Frequently asked questions

How much do cottages in Western Shore of Maryland cost?
You can expect to pay between AU$300 and AU$1,862 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 116 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.

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