Holiday Homes in Arnold

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Featured Holiday Homes in Arnold

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (10)
"TVs don’t work. Tile by fridge broken. Dangerous. House is awesome. Hot tub works great. If fixed we will be back for Skibs games. Cheers. Ty !! "
The price is AU$808
includes taxes & fees
1 Dec - 2 Dec
Edgewater/Mayo Getaway!

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

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

10.0 out of 10, Exceptional, (16)
"Perfect place for Ravens Game. Walking distance to stadium. Super clean. Nice neighbors. Responsive host. "
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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

10.0 out of 10, Exceptional, (202)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Private Waterfront Woods | Dock, Kayaks, Views

10.0 out of 10, Exceptional, (14)
"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

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

9.8 out of 10, Exceptional, (59)
"This condo was absolutely perfect. It is super cute and clean. Three bedrooms as advertised. Very quiet area. We love the fact that it has a piano. We would definitely love to stay here again. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Stylish 4-bedroom whole house with plenty of parking

9.2 out of 10, Wonderful, (15)
" It was great "
Stylish 4-bedroom whole house with plenty of parking

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

10.0 out of 10, Exceptional, (12)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house for a fun weekend. Super clean and comfortable. Withing walking distance of good restaurants and stadiums. Will definately look to book this location again when we are back in Baltimore."
Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,350
includes taxes & fees
2 Dec - 3 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (11)
"The Bennett House not only lived up to its pictures online, the cleanliness, abundance of extra special touches, communication with the host, and more surpassed our expectations. The beds were extra comfy, the kitchen, fully stocked, the bathrooms, adorned with the fluffiest white towels and extra toiletries . . . and I can't say enough about the front porch. Even though clouds cloaked the sky when we arrived and when we left, sunshine streamed through our Annapolis trip because of the Bennett...
Bennett House (entire):Haven in Historic Annapolis

Downtown Home - Close to Topgolf, Ravens Stadium, Orioles Park, UM Baltimore

7.8 out of 10, Good, (8)
"The property had many rooms, and the back yard was nice. Other than that it had a musty smell/ smelled like cats when we first entered. The ceiling in the basement was maybe 6/7 ft high where we had to duck while walking around. The air conditioning was set on 70 with a lock, which was fine, BUT it didn’t work in the top two rooms where the temp was well over 90 during the day. It’s a good place to stay for one or two nights but if you plan on doing longer I wouldn’t recommended it. I will say...
The price is AU$632
includes taxes & fees
10 Dec - 11 Dec
Downtown Home - Close to Topgolf, Ravens Stadium, Orioles Park, UM Baltimore

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (61)
"What an amazing place... the sunsets, the house, the pool, the amenities... absolutely everything was perfect! The owner was super helpful! "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar

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

10.0 out of 10, Exceptional, (10)
"Very clean and a great place overall! Will be back in our future visits to Maryland! "
The price is AU$558
includes taxes & fees
12 Dec - 13 Dec
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

ACROSS FROM STADIUM - walk to downtown Annapolis.

9.6 out of 10, Exceptional, (42)
"Property was great and accommodated 7 of us easily. Quiet location, close to everything for our stay in Annapolis. "
ACROSS FROM STADIUM - walk to downtown Annapolis.
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 Arnold

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

10.0 out of 10, Exceptional, (16)
"Perfect place for Ravens Game. Walking distance to stadium. Super clean. Nice neighbors. Responsive host. "
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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

10.0 out of 10, Exceptional, (202)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.