Search Holiday Rentals in Western Shore of Maryland

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Top Holiday Rentals in Western Shore of Maryland

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,143
includes taxes & fees
6 May - 7 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Cozy townhome near Stadium/ Camden Yards/Inner Harbor
10.0 out of 10, Exceptional, (11)
"It was a short trip but our stay was great. Place was exactly as noted in listing. Even though it snowed and was vey cold our stay was good."
Cozy townhome near Stadium/ Camden Yards/Inner Harbor
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (32)
"Really wonderful host. The apartment was spacious and immaculate. It worked wonderfully for our family gathering with our midshipman."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Tiki bar jacuzzy and rooftop close to M&T stadium
10.0 out of 10, Exceptional, (5)
"Loved it , when we walked up the steps to the main bedroom the railing fell. Also i was taking a jucuzzi bath and the tiling fell off the side. Other than those little things the property is amazing "
The price is £377
includes taxes & fees
5 May - 6 May
Tiki bar jacuzzy and rooftop close to M&T stadium
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (16)
"Overall, my family enjoyed the cleanliness and charm of the carriage house. Would come back again!"
The price is £367
includes taxes & fees
5 May - 6 May
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Rooftop Deck Escape! Free Parking!
10.0 out of 10, Exceptional, (2)
"We rented Robert’s property to spend Easter with our mid 20s kids and their partners. We wanted a place that would be fun for everyone to hangout and it was perfect. The darts and especially the hand shuffleboard were great fun. And the kitchen and dining area was large enough to cook and serve seven people. It’s also in a great area, within walking distance to coffee shops, restaurants and bars."
The price is £227
includes taxes & fees
6 May - 7 May
Rooftop Deck Escape! Free Parking!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
Luxe Houseboat: Breathtaking Skyline 360 Views
10.0 out of 10, Exceptional, (9)
"Great atmosphere and surroundings. Loved it!"
The price is £665
includes taxes & fees
13 May - 14 May
Luxe Houseboat: Breathtaking Skyline 360 Views
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (42)
"Great location - walkable to Downtown Annapolis and the stadium. House was very clean and has all the features and amenities you need for a comfortable stay!"
Recently Renovated Annapolis Home - Conveniently Located
Cheerful 3-Bedroom House in Downtown Annapolis
10.0 out of 10, Exceptional, (10)
"We were looking for a place to spend our Thanksgiving and this was perfect! Great location close to downtown Annapolis. Marina was awesome - she was super responsive and took time during the holiday weekend to answer our questions. We loved that there were two places to hang out. Kitchen was well stocked. Lots of extra towels and blankets. General notes: The sofa bed in the basement is not a pull out as expected but is technically a twin bed and the bunk bed is actually a twin with a trundle...
Cheerful 3-Bedroom House in Downtown Annapolis
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown
10.0 out of 10, Exceptional, (14)
"The space was perfect and very clean. The plug-ins were a little intense for me and gave me a headache. Once I unplugged them and aired out the space, I was fine."
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is £551
includes taxes & fees
8 May - 9 May
Charming Annapolis WaterVIEW Home
💎 Sanitized*LUXURY* Relaxing*MODERN APT In the HEART OF DOWNTOWN
9.8 out of 10, Exceptional, (12)
"The apt was gorgeous! Building too! Great location to walk and attend cheer comp at convention center and also Oriole baseball game. Would love to stay here again."
The price is £217
includes taxes & fees
5 May - 6 May
💎 Sanitized*LUXURY* Relaxing*MODERN APT In the HEART OF DOWNTOWN
Luxurious, Inner Harbor Federal Hill Townhome
9.8 out of 10, Exceptional, (9)
"Property is in a great location within walking distance to bars/restaurants, inner harbor and convention center. Plenty of space to spread out for a larger group looking to stay together"
The price is £383
includes taxes & fees
2 Jun - 3 Jun
Luxurious, Inner Harbor Federal Hill Townhome
ROOST Baltimore
4.5 star property
9.6 out of 10, Exceptional, (129)
"Large rooms. Nice appliances. "
The price is £206
includes taxes & fees
6 May - 7 May
ROOST Baltimore
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino
9.6 out of 10, Exceptional, (5)
"I'm so glad I chose to stay at Skys-Home! This place truly feels like a home away from home. It has everything I could possibly need and want. The hosts have thought of everything - from providing wine, water bottles, and a variety of drinks to snacks and parking spaces. The home is immaculately clean and perfectly located, just a short distance from all the downtown attractions. The host is incredibly responsive and made sure my stay was comfortable and stress-free. I highly recommend Skys-Home...
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
9.6 out of 10, Exceptional, (33)
"Love the layout of the house"
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
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See all available properties in Western Shore of Maryland
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.

Western Shore of Maryland Holiday Rental Travel Info

Other types of properties in Western Shore of Maryland you may be interested in

Renaissance Baltimore Harborplace Hotel
4.0 star property
8.4 out of 10, Very good, (2067)
"Enjoyed my experience at this hotel manager is amazing "
The price is £167
includes taxes & fees
19 May - 20 May
Renaissance Baltimore Harborplace Hotel
Hyatt Regency Baltimore Inner Harbor
4.0 star property
8.4 out of 10, Very good, (1749)
"The view from the room of the Inner Harbor was stunning!"
The price is £177
includes taxes & fees
12 May - 13 May
Hyatt Regency Baltimore Inner Harbor
Hyatt Place Baltimore Inner Harbor
3.5 star property
8.2 out of 10, Very good, (1431)
"Excellent location and friendly, helpful staff. Our only feedback is that it was loud at night. Our room happened to be above a bar/restaurant and the music was very loud one night. "
The price is £123
includes taxes & fees
12 May - 13 May
Hyatt Place Baltimore Inner Harbor
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.

Everything you need to know about Western Shore of Maryland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Western Shore of Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Western Shore of Maryland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Western Shore of Maryland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Western Shore of Maryland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Western Shore of Maryland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Western Shore of Maryland holiday rentals we have selected for you start as low as £206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Western Shore of Maryland rentals

At Expedia, we put the best Western Shore of Maryland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Western Shore of Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Western Shore of Maryland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Western Shore of Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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