Holiday Homes in Maryland

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Featured Holiday Homes in Maryland

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10.0 out of 10, Exceptional, (15)
"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

9.8 out of 10, Exceptional, (118)
"We were in Ocean City for our son's wedding. The condo fit our family and was in a great spot. We were able to walk up to the beach and take long walks on the beach. The condo was clean, large and had lots of parking. Convenient to the strip. Thank you!"
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

Serene Mountain Escape: Hot Tub, Foosball, Views

9.4 out of 10, Exceptional, (3)
"House was very clean and well appointed. Nice location"
Serene Mountain Escape: Hot Tub, Foosball, Views

Four Bedroom Oceanside Townhome with Pool and View

8.0 out of 10, Very good, (1)
"Overall, it was a nice stay. The property was found as advertised; however, there was an infestation of ants that we battled all week. There were ant traps in the property when we arrived and we purchased more throughout the week. The bedding was stained in some places as well. The accuracy of information about access to the pool was a bit frustrating at first. But we got that sorted out rather quickly. The location to the ocean was amazing and very convenient with young children!"
Four Bedroom Oceanside Townhome with Pool and View

La Maison - Stunning waterfront views with pool

10.0 out of 10, Exceptional, (93)
"Amazing time the view was to die for , host was awesome "
La Maison - Stunning waterfront views with pool

Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

8.2 out of 10, Very good, (17)
"Condo was in great condition, just as described. Awesome location. "
Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

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

Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

9.6 out of 10, Exceptional, (16)
"The house was very nice and spacious . Also very clean. Appreciate that our dogs were allowed. Close to many restaurants and activities."
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

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

9.6 out of 10, Exceptional, (18)
"This property meets all expectations! The host was very easy to communicate with. I loved the quaintness of the area and the ease of access to the highways was so nice! I would highly recommend this property to anyone visiting the Baltimore area!"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

Water front, open bay views from both decks!!

10.0 out of 10, Exceptional, (48)
"Great place to stay!"
Water front, open bay views from both decks!!

Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

7.8 out of 10, Good, (19)
"Took my boys with friends for a long weekend and enjoyed our stay. Place was close enough to walk to beach and we enjoyed our stay. Place was easy to communicate with them during the stay."
Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

10.0 out of 10, Exceptional, (270)
"Our family rented Full Circle cottage in order to visit our daughter at WVU for a football game. It is about 45 minutes away. The cottage surpassed our expectations. It was spotless and the decor was Beautiful! The pictures did not do justice. The owners go above and beyond to make your stay special. Even cinnamon rolls in the freezer for the morning. The owner met us on arrival to show us around and made the beautiful, huge dining table. We had 10 people and more than enough room. I...
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (110)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

Charming "Cream of the Crop" Cape ~❤️of Middletown

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AU$553
includes taxes & fees
30 Dec - 31 Dec
Charming "Cream of the Crop" Cape ~❤️of Middletown

Private Waterfront Woods | Dock, Kayaks, Views

9.8 out of 10, Exceptional, (15)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views

4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!

9.4 out of 10, Exceptional, (49)
"Great location to downtown. Parking on the street is hit or miss. Only issue we had was the wifi… unable to work remotely from this property because wifi is not strong enough."
4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook

⭐️UPSCALE House Steps to Ocean 3 Balconies Pool⭐️

9.6 out of 10, Exceptional, (22)
"Check in was very smooth. Home is beautiful and in excellent condition. Bathrooms were very clean, which is a big deal. Floors weren't as clean, so vacuum cleaner came in handy. Quieter area than closer to boardwalk, (which we were thankful for), but still plenty of food and shopping in walking distance. Just a very short walk to the beach. Overall, a great long weekend!"
⭐️UPSCALE House Steps to Ocean 3 Balconies Pool⭐️

The Madison

10.0 out of 10, Exceptional, (25)
"My friend and I enjoyed five nights at the Madison. We were very happy with everything. The beds and pillows were wonderful. Loved the decor and cleanliness. The location was great for exploring downtown Frederick and Carrol Creek and day trips to Annapolis, DC, and Harper’s Ferry. "
The Madison
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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