Western Shore of Maryland Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Western Shore of Maryland holiday rentals

Sun-loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

9.8 out of 10, Exceptional, (38)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is HK$973
HK$2,210 total
includes taxes & fees
10 Dec - 11 Dec
Soul Oasis - home on the Chesapeake Bay
Interior
Convention Center corporate apartments

Apartment in Downtown Baltimore

4.0 star property
The price is HK$833
HK$2,068 total
includes taxes & fees
14 Dec - 15 Dec
Convention Center corporate apartments
Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$1,237
HK$3,875 total
includes taxes & fees
14 Dec - 15 Dec
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Printers
Hudson house

Residence in Canton

3.5 star property
The price is HK$1,206
HK$2,585 total
includes taxes & fees
10 Dec - 11 Dec
Hudson house
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage in Owings

10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is HK$834
HK$1,948 total
includes taxes & fees
11 Dec - 12 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Fridge, microwave, oven, stovetop
* Private Suite Full of Style & Comfort *

Apartment in Lutherville-Timonium

9.2 out of 10, Wonderful, (42)
"Owners were receptive when needed. All went smoothly. "
United States
David M.
The price is HK$661
HK$1,348 total
includes taxes & fees
22 Dec - 23 Dec
* Private Suite Full of Style & Comfort *
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in North Beach

10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is HK$664
HK$2,556 total
includes taxes & fees
10 Dec - 11 Dec
Walk to Beach! King Bed & Free Beach Passes
1 bedroom, WiFi, bed sheets, wheelchair access
Restful Non-Shared Basement Suite In Harford MD

Holiday Home in Bel Air

10.0 out of 10, Exceptional, (2)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is HK$428
HK$866 total
includes taxes & fees
17 Dec - 18 Dec
Restful Non-Shared Basement Suite In Harford MD
Outdoor dining
Rollingside Guest Suite

Apartment in Catonsville

10.0 out of 10, Exceptional, (54)
"Perfect accommodations for shows at Merriweather - and to venture downtown or Ellicott City. Cozy, clean and beautiful yard with the pool as a bonus. Will definitely be back. "
United States
Sara T.
The price is HK$661
HK$1,258 total
includes taxes & fees
10 Dec - 11 Dec
Rollingside Guest Suite
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Holiday Home in Annapolis

9.2 out of 10, Wonderful, (16)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
The price is HK$1,375
HK$2,898 total
includes taxes & fees
10 Dec - 11 Dec
Wright's Cottage- Pet's Welcome & EV Charging
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Holiday Home in Bel Air

10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
The price is HK$953
HK$2,442 total
includes taxes & fees
16 Dec - 17 Dec
Small House on Gentleman’s Farm
Fridge, microwave, oven, stovetop
Cozy Modern Micro Apt in the Heart of Fells Point!

Apartment in Fells Point

9.0 out of 10, Wonderful, (30)
"We had such a great stay at the property. Everything was clean and welcoming. It was the perfect little place/space for my wife my 3 yr old son and myself. The street parking in the area was also good. We were able to find a spot right around the corner. The location of the property in relation to a lot of the sites in Fells Point was perfect as well. Everything 5 stars we would definitely recommend and We would definitely book again! "
United States
Bryan S.
The price is HK$805
HK$1,883 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Modern Micro Apt in the Heart of Fells Point!
Private kitchen
Entire House 1BD King Bed near Downtown

Apartment in Hollins Market

3.0 star property
7.2 out of 10, Good, (5)
"I had a great stay at this place. The house was clean and had all amenities described, such as kitchen, laundry machine, TV, and free parking. Check-in was smooth with the door entry codes. Exploring Baltimore was easy because the downtown was like 10 mins walking distance and public transportation options were nearby. Well spent dollars. "
United States
Nathan
The price is HK$592
HK$852 total
includes taxes & fees
17 Dec - 18 Dec
Entire House 1BD King Bed near Downtown
Smart TV, books
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Point Lookout

9.4 out of 10, Exceptional, (8)
"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."
United States
Marc C.
The price is HK$1,113
HK$2,529 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,611
HK$3,220 total
includes taxes & fees
11 Dec - 12 Dec
Waterfront Oasis of Annapolis Star
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Houseboat in Baltimore

10.0 out of 10, Exceptional, (11)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is HK$1,838
HK$4,350 total
includes taxes & fees
10 Dec - 11 Dec
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Property grounds
Cozy Farm Home Near I83. Minutes from wedding venues! Fire pit, hiking trails!

Apartment in White Hall

10.0 out of 10, Exceptional, (36)
"We chose this property since it is located reasonably close to our family (grandchildren) and to the Manor Tavern and Oregon Grille our favorite restaurants in the area. Beautiful, private area in Maryland horse country!!"
United States
Donald F.
The price is HK$1,027
HK$2,130 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Farm Home Near I83. Minutes from wedding venues! Fire pit, hiking trails!
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Holiday Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is HK$1,175
HK$3,889 total
includes taxes & fees
10 Dec - 11 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Sun-loungers
Cottage Located on the Patuxent River!

Cottage in Prince Frederick

10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is HK$2,066
HK$2,495 total
includes taxes & fees
10 Dec - 11 Dec
Cottage Located on the Patuxent River!
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in North Beach

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$765
HK$3,164 total
includes taxes & fees
10 Dec - 11 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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
"Clean upscale rooom..bed was amazing "
Theo 1-night trip
Posted 8 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Western Shore of Maryland

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