Photo by Katelyn McGlynn

Western Shore of Maryland holiday rentals

We found 2,857 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Western Shore of Maryland

Showing deals for:18 Dec - 25 Dec

Room
Property grounds
Dining
Exterior
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
AU$3,169
for 7 nights, 1 houseboat
AU$453 per night
includes taxes & fees
Houseboat on Solomons Island
Open concept from living room to kitchen
Spacious fully equipped kitchen
View from dining room to kitchen
Living area
Exceptional
(8 reviews)

Entire home, great location, no cleaning fee

Havre De Grace

9% off
AU$4,073
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Entire home, great location, no cleaning fee
Room
Exterior
Dining
Property grounds
Exceptional
(11 reviews)

Cozy 1-bedroom bungalow in quaint Darlington with AC

Darlington

18% off
AU$1,238
for 7 nights, 1 home
AU$177 per night
includes taxes & fees
Cozy 1-bedroom bungalow in quaint Darlington with AC
Interior
Wake up to serene water views from the primary suite
Dine with panoramic waterfront views—perfect for unforgettable group meals
Enjoy morning coffee or evening drinks on the private waterfront deck
Exceptional
(21 reviews)

🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1

Scotland

8% off
AU$7,484
for 7 nights, 1 home
AU$1,069 per night
includes taxes & fees
🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1
Exterior detail
Private kitchen
Room
Dining
Exceptional
(24 reviews)

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point

7% off
AU$5,155
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
Dining room showing steps to loft.  Dining room seats 8-10
French doors from kitchen go to backyard wrap-around deck
Ariel view of the house, pool, dock, lagoon and beautiful Chesapeake Bay.
View of the lagoon and Chesapeake bay from the living room.
Wonderful
(22 reviews)

Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays

Lexington Park

5% off
AU$7,182
for 7 nights, 1 home
AU$1,026 per night
includes taxes & fees
Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays
Dining
Private kitchen
Living area
Dining
Excellent
(11 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,074
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
outdoor space
Terrace/patio
Living room with wood fireplace and second TV with basic channels
upstairs bedroom w/ King size bed and space for queen air mattress
Exceptional
(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
AU$5,319
for 7 nights, 1 home
AU$760 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Local artwork is displayed and for sale, if you wish to take a memory home.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Twin size sofa/futon for a 3rd person.
Separate entryway with electronic keypad.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,482
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Living area
Terrace/patio
Exterior
Private kitchen
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,209
for 7 nights, 1 home
AU$458 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
A dining room table expands to 12 seats with a view.  Two extensions not show.
Piney Point Light House and underwater park with German U-Boat is 5 miles away.
A quiet and relaxing road with an abundance of deer, birds, squirrels, and crab.
Property grounds
Exceptional
(66 reviews)

Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset

Tall Timbers

12% off
AU$2,901
for 7 nights, 1 cottage
AU$414 per night
includes taxes & fees
Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset
Living area
Private kitchen
Room
Interior
Exceptional
(14 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

7% off
AU$12,295
for 7 nights, 1 home
AU$1,756 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Interior
Property grounds
Dining
Water view from the kitchen
Exceptional
(36 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$7,003
for 7 nights, 1 home
AU$1,000 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Private kitchen
Dining
Living area
Living area
Exceptional
(42 reviews)

Charming 4 bedroom home just steps to the water!

Baltimore

8% off
AU$5,983
for 7 nights, 1 home
AU$855 per night
includes taxes & fees
Charming 4 bedroom home just steps to the water!
Living area
Exterior
Property grounds
Dining
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
AU$7,986
for 7 nights, 1 home
AU$1,141 per night
includes taxes & fees
Magnificent Water Front Property
Exterior
entryway
loft bedroom
dining area
Exceptional
(61 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
AU$1,873
for 7 nights, 1 cottage
AU$268 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
A wall of windows in main living area offers stunning panoramic Potomac views.
Deck view at dusk.
A well appointed kitchen with everything you’d need to make a gourmet meal.
Dining room
Exceptional
(17 reviews)

Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views

Leonardtown

8% off
AU$4,412
for 7 nights, 1 home
AU$630 per night
includes taxes & fees
Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views
Open-concept living area and kitchen
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Beautiful North Bach, MD
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,893
for 7 nights, 1 apartment
AU$556 per night
includes taxes & fees
Unbelievable beach views for 6
Living area
Pool
Dining
Exterior
Exceptional
(59 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

16% off
AU$4,762
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Dining
Private kitchen
Living area
Interior
Exceptional
(13 reviews)

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Riva

21% off
AU$4,056
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Outdoor dining
Exterior
Property grounds
Room
Exceptional
(269 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
AU$1,676
for 7 nights, 1 cottage
AU$239 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Dining
Living area
Interior
Living area
Exceptional
(11 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
AU$5,793
for 7 nights, 1 home
AU$828 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Living area
Dining
Outdoor dining
Private kitchen
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$6,801
for 7 nights, 1 home
AU$972 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Dining
Terrace/patio
Back yard and fire pit
Private kitchen
Exceptional
(49 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
AU$5,308
for 7 nights, 1 home
AU$758 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

The vibrant area of Western Shore of Maryland awaits your stay

Enjoy the art galleries and other features of Western Shore of Maryland. Revered for its horse riding, sporting events and bars, this city is both cosmopolitan and welcoming. Take in top local attractions such as M&T Bank Stadium and Baltimore Inner Harbor Marina. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Western Shore of Maryland

Are you hoping to discover top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that Western Shore of Maryland has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Severna Park Golf Center (1.6 mi / 2.5 km)
  • Bay Hills Golf Club (3.2 mi / 5.2 km)
  • Maryland Renaissance Festival (3.6 mi / 5.8 km)
  • Renditions Golf Club (11 mi / 17.8 km)
  • Thanksgiving Farm Wines (12 mi / 19.2 km)
  • Paul Reed Smith Guitars (12 mi / 19.4 km)

Exploring the natural landscape of Western Shore of Maryland

Whether you're looking for adventure or just want to take in the scenery, Western Shore of Maryland is a great place to get outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (6 mi / 9.7 km)
  • Bay Ridge Beach (6.9 mi / 11.1 km)
  • Sandy Point Beach (7.5 mi / 12.1 km)
  • Fort Smallwood Park (7.8 mi / 12.6 km)
  • Northern Chesapeake Bay (11 mi / 17.6 km)
  • Allen Pond Park (12.5 mi / 20.2 km)

Transport options to and around Western Shore of Maryland

The nearest airport is in Baltimore Washington International Airport (BWI), located 12.8 mi (20.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Fort Meade, MD (FME-Tipton), which is 12.9 mi (20.7 km) away.

If you prefer to travel by train, Odenton Station, Baltimore-Washington International Airport Station and Annapolis Junction Savage Station are the main stations in the city. It's easy to get around Western Shore of Maryland by catching a ride on the metro at Cromwell-Glen Burnie Station, Ferndale Station or BWI Thurgood Marshall Airport Metro Station.

Frequently asked questions

What is the best area to stay in Western Shore of Maryland when booking a holiday home?
Alexandria is among the more popular locations to book a holiday home in Western Shore of Maryland. Searching for some cool things to do here? Don't miss George Washington Masonic National Memorial and George Washingtons Mount Vernon.
What is the most popular type of holiday home accommodation in Western Shore of Maryland?
According to our data, houses are the most sought-after property type in Western Shore of Maryland. But having said that, everyone's idea of an epic stay isn't the same. Stayz has holiday homes of all shapes and sizes, so you're sure to discover the perfect fit.
How much does it cost to rent a holiday home in Western Shore of Maryland?
Length of stay, season and property type are among the factors that can determine the price of a holiday home. Simply click on your travel dates to find your dream escape. From cosy chalets to plush villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Western Shore of Maryland?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Put in your Western Shore of Maryland travel dates to view your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the amenities and features you want.
What are popular home amenities in Western Shore of Maryland?
A fridge, off-street parking options and a microwave oven top the list of most popular home amenities in Western Shore of Maryland. Whether you plan to travel on your own, with your better half or a group of family members, Stayz can help you find a holiday home that fits your tastes with all the conveniences you're looking for.
Are there large group holiday homes in Western Shore of Maryland?
With 151 properties that can sleep 10 guests or more in Western Shore of Maryland, there's no need to keep anyone off the invite list. From extended family holidays to events like weddings and birthday parties, Stayz can help you find a large group home that fits the occasion.
What are the top attractions for families in Western Shore of Maryland?
Keeping the kids amused during your stay in Western Shore of Maryland is simple with these fabulous family-friendly attractions:
  • Oriole Park at Camden Yards
  • National Aquarium in Baltimore
  • Arundel Mills Mall
Can I find two-bedroom holiday homes in Western Shore of Maryland?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 246 two-bedroom holiday homes Western Shore of Maryland has to offer.
Are there holiday homes with WiFi in Western Shore of Maryland?
Whether you want to stay in touch with world events, check emails or post a pic to social media, there are 525 holiday homes with WiFi in Western Shore of Maryland. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in Western Shore of Maryland?
The age limit can differ between properties on Stayz, so be sure to look at the rules of the holiday home in Western Shore of Maryland you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Western Shore of Maryland for?
The length of time you can rent a holiday home in Western Shore of Maryland varies according to the property. Just enter your chosen travel dates to display a list of options offering extended stays. With loads of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover the perfect place to call your home away from home in Western Shore of Maryland.

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