Upper Marlboro Holiday Rentals

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Holiday Rentals in Upper Marlboro

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$600
includes taxes & fees
27 July - 28 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is NZ$2,315
includes taxes & fees
21 July - 22 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is NZ$2,182
includes taxes & fees
14 July - 15 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is NZ$912
includes taxes & fees
5 Aug - 6 Aug
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is NZ$1,383
includes taxes & fees
22 July - 23 July
Charming Annapolis WaterVIEW Home

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is NZ$1,366
includes taxes & fees
14 July - 15 July
Charming Cottage with Hot Tub 1 Block from the Bay

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is NZ$1,136
includes taxes & fees
5 Aug - 6 Aug
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is NZ$791
includes taxes & fees
13 July - 14 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (15)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is NZ$656
includes taxes & fees
16 July - 17 July
Beach Home with King Bed and Beach Passes in a Cute Town

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is NZ$1,157
includes taxes & fees
21 July - 22 July
Freshly renovated 3-story home 1 block from USNA!

★ Midcentury Modern Getaway ★ Prime Location ★

10.0 out of 10, Exceptional, (33)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
The price is NZ$1,069
includes taxes & fees
13 July - 14 July
★ Midcentury Modern Getaway ★ Prime Location ★

Cozy Cottage By The Beach-Pet Friendly

10.0 out of 10, Exceptional, (1)
"Had a great stay. Very clean. As advertised. "
The price is NZ$846
includes taxes & fees
22 July - 23 July
Cozy Cottage By The Beach-Pet Friendly

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (69)
"Comfortable, clean home. Convenient walking distance to historic downtown Annapolis. "
The price is NZ$708
includes taxes & fees
29 July - 30 July
Cozy 2br home w/ parking in downtown Annapolis

Dean Street's Lower Deck House!

The price is NZ$748
includes taxes & fees
3 Aug - 4 Aug
Dean Street's Lower Deck House!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

10.0 out of 10, Exceptional, (17)
"Accommodating hosts, charming house and great location! "
The price is NZ$1,028
includes taxes & fees
31 July - 1 Aug
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Chesapeake Comfort, Annapolis.

10.0 out of 10, Exceptional, (15)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
The price is NZ$797
includes taxes & fees
22 July - 23 July
Chesapeake Comfort, Annapolis.

Mins to DTA - King Beds - Parking

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
The price is NZ$914
includes taxes & fees
22 July - 23 July
Mins to DTA - King Beds - Parking

Spacious 4 Bedroom Home w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is NZ$910
includes taxes & fees
13 July - 14 July
Spacious 4 Bedroom Home w/ Hot Tub

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."
The price is NZ$619
includes taxes & fees
22 July - 23 July
Large 2 bedroom house with private parking in a nice neighborhood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

10.0 out of 10, Exceptional, (6)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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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Frequently asked questions

Are there holiday rentals in Upper Marlboro?

Yes, there are holiday rentals close to the most popular sights in Upper Marlboro, or you can select a more secluded option if you're looking for a relaxing stay. Upper Marlboro is known for its festivals and football games. Make sure you have time to check out the architecture while you're in the area.

What are some of the best holiday rentals that Upper Marlboro has to offer?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This holiday home rental outside of Upper Marlboro offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals will I find in Upper Marlboro?

Choose from 10 Expedia holiday rentals in Upper Marlboro for a memorable holiday.

What can I see and do in Upper Marlboro?

Patuxent River and Marlton Neighborhood Park are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places such as White House and Washington Navy Yard.

What are holiday rentals like in Upper Marlboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upper Marlboro. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.