Search Vacation Homes in Western Shore of Maryland

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Compare 767 Vacation Homes in Western Shore of Maryland with updated reviews, rates, and availability.

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

9.6 out of 10, Exceptional, (21)
"Couldn't ask for a better location for walking to The Bank. Parking pass good on game days. Had no problem parking right out front. Excellent communication with host and house was very nicely appointed! Stairs wider and safer than most in Pigtown"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

Rooftop Deck Escape! Free Parking!

8.8 out of 10, Excellent, (26)
"Overall place was great and was in perfect location for our family trip to a ravens game. However we were looking forward to the fire pit on the roof but there was no full propane tanks. There was multiple empty propane tank"
The price is SAR 409
SAR 1,014 total
includes taxes & fees
2 Mar - 3 Mar
Rooftop Deck Escape! Free Parking!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (68)
"This is a great location The house is clean and updated. We enjoyed and would stay here again."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (207)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (31)
"What a perfect house in a central location to all things walkable in Downtown Annapolis. House had everything we needed, was comfortable and clean. "
The price is SAR 649
SAR 2,553 total
includes taxes & fees
3 Mar - 4 Mar
Freshly renovated 3-story home 1 block from USNA!

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (16)
"One of if not the best VRBO I have ever stayed in. Incredible property and host"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

9.6 out of 10, Exceptional, (14)
"Turns out the property was just as it looked online. Location was great...close to Blue Moon Two (a fantastic place for an amazing breakfast), grocery and a couple of small bars. Easy access for Lyft to get us around town and definitely a plus to have parking included! Miles, our host, was great and responded super quickly to any questions we had. Would recommend. "
The price is SAR 750
SAR 1,456 total
includes taxes & fees
6 Mar - 7 Mar
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (5)
"This home was exactly as described. Very clean, comfortable and well equipped. This home was beautifully designed, well furnished and had everything we need to enjoy a short friends getaway. Thank you for a wonderful stay. "
Brand New Spacious Luxury Home

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

10.0 out of 10, Exceptional, (14)
"This property from website fit the beds and bathrooms we needed so everyone got their own bed. When we opened the front door it was better looking in person than on web.Would absolutely recommend this place and we will definitely be back."
The price is SAR 1,031
SAR 1,313 total
includes taxes & fees
20 Mar - 21 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Charming Home: Parking, Sleeps 10, WFH Space

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great Location for the event we attended. Plenty of room and bathrooms for our family. Would stay again when visiting Baltimore.Susan Church "
Charming Home: Parking, Sleeps 10, WFH Space

House on the Gwynns Falls

8.6 out of 10, Excellent, (10)
"Mary was a very gracious host and very accommodating when we added a 6th person at the last minute. She was always very responsive when I messaged her and greeted us with a warm welcome when we arrived. The house is a beautiful historic home tucked away in quiet neighborhood "
The price is SAR 634
SAR 836 total
includes taxes & fees
1 Apr - 2 Apr
House on the Gwynns Falls

Welcome to the Charm City Getaway!

9.4 out of 10, Exceptional, (3)
"We had a pleasant stay in Mr. Farrow’s home. It’s spacious, clean, and felt like home. Doc made sure we had everything we needed. We barely noticed that he was sharing his home with us. He was very accommodating to our needs and responded to us within a reasonable time. We would definitely stay here again."
The price is SAR 566
SAR 1,581 total
includes taxes & fees
1 Apr - 2 Apr
Welcome to the Charm City Getaway!

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (24)
"This was by far the best Property we have ever stayed at. We were in town for a cheer competition with 6 moms and 7 daughters. The upstairs room had beds for every girl plus some! The house was extremely clean and the host literally though about EVERYTHING. From local menus, to games for all ages and even to-go containers in the kitchen! (which we always forget!) It was so comfortable and enjoyable, no one wanted to leave!"
River Haven with Hot Tub | 4 Bed, 3.5 Bath
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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Other property types in Western Shore of Maryland

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Spectacular Penthouse at 39 west.

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 766
SAR 1,425 total
includes taxes & fees
14 Mar - 15 Mar
Spectacular Penthouse at 39 west.
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.