Search Vacation Homes in Western Shore of Maryland

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Compare 778 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!

9.0 out of 10, Wonderful, (24)
"We had a great time, plenty of space for family of 8 with close distance to the aquarium. "
The price is AED 419
AED 1,035 total
includes taxes & fees
2 Feb - 3 Feb
Rooftop Deck Escape! Free Parking!

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

9.8 out of 10, Exceptional, (65)
"Clean and close to everything. "
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, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (29)
"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "
The price is AED 544
AED 2,342 total
includes taxes & fees
2 Feb - 3 Feb
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

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (21)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA

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

10.0 out of 10, Exceptional, (15)
"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

9.4 out of 10, Exceptional, (12)
"Clean, comfortable home with lovely rooftop patio! "
The price is AED 735
AED 1,413 total
includes taxes & fees
3 Feb - 4 Feb
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (4)
"Property is great for families!!"
Brand New Spacious Luxury Home

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

10.0 out of 10, Exceptional, (13)
"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 AED 1,010
AED 1,319 total
includes taxes & fees
3 Feb - 4 Feb
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!

9.6 out of 10, Exceptional, (29)
"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, (2)
"A great place to stay with homie accommodations.Would definitely use again if traveling through Baltimore."
Charming Home: Parking, Sleeps 10, WFH Space

House on the Gwynns Falls

8.8 out of 10, Excellent, (8)
"We needed a getaway near Baltimore so we could visit some family and attractions. The location was easy to navigate to and is nestled in a historic village. We enjoyed the ambiance of the house and the host made sure we were comfortable. We highly recommend this stay to anyone who enjoys a unique and quiet getaway. We particularly enjoyed listening to the nearby waterfall from the upstairs balcony. The house was clean and stocked with necessities. We would love to return as we found many places...
The price is AED 621
AED 810 total
includes taxes & fees
3 Feb - 4 Feb
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 AED 555
AED 1,548 total
includes taxes & fees
2 Feb - 3 Feb
Welcome to the Charm City Getaway!
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

Baltimore executive Furnished rentals

4.0 star property
8.0 out of 10, Very Good, (2)
"I highly recommend this property if you’re visiting the Baltimore area. Very spacious for myself, my husband and our 4 kids. Lorraine checked in on us every other day and Mr. Derrick made sure everything was in order upon our arrival."
The price is AED 1,196
AED 1,883 total
includes taxes & fees
28 Feb - 1 Mar
Baltimore executive Furnished rentals

⭐️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

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.
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.