Holiday Homes in Greater Upper Marlboro

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Greater Upper Marlboro and around

Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €290
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

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!"
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun-loungers, beach towels

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 €1,194
includes taxes & fees
25 Aug - 26 Aug
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (53)
"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 €636
includes taxes & fees
20 Aug - 21 Aug
Charming Annapolis WaterVIEW Home
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €443
includes taxes & fees
19 Aug - 20 Aug
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
Neptune by the Water - Pet Friendly Fenced Yard
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

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 "
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Freshly renovated 3-story home 1 block from USNA!
Fridge, microwave, oven, stovetop

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (35)
"We loved our stay! The property is lovely, well appointed and couldn’t be in a better location! We can’t wait to come back!"
Freshly renovated 3-story home 1 block from USNA!
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is €1,226
includes taxes & fees
8 Sept - 9 Sept
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fisher House: Steps From USNA + Covered Parking!
Fridge, microwave, oven, stovetop

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is €673
includes taxes & fees
17 Aug - 18 Aug
Fisher House: Steps From USNA + Covered Parking!
★ Midcentury Modern Getaway ★ Prime Location ★
3 bedrooms, iron/ironing board, travel cot, WiFi

★ 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 €502
includes taxes & fees
18 Aug - 19 Aug
★ Midcentury Modern Getaway ★ Prime Location ★
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is €344
includes taxes & fees
9 Sept - 10 Sept
Cozy 2br home w/ parking in downtown Annapolis
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
Terrace/patio

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

9.8 out of 10, Exceptional, (23)
"Great location, great host! "
The price is €969
includes taxes & fees
27 Aug - 28 Aug
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
Chesapeake Comfort, Annapolis.
Terrace/patio

Chesapeake Comfort, Annapolis.

10.0 out of 10, Exceptional, (17)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
Chesapeake Comfort, Annapolis.
Mins to DTA - King Beds - Parking
Dining

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 €453
includes taxes & fees
19 Aug - 20 Aug
Mins to DTA - King Beds - Parking
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is €497
includes taxes & fees
20 Aug - 21 Aug
Edgewater/Mayo Gateaway w/ Hot Tub
Holly Hill Haven - Sleeps 10
TV, books, offices

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
Holly Hill Haven - Sleeps 10
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, books

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is €332
includes taxes & fees
20 Aug - 21 Aug
Large 2 bedroom house with private parking in a nice neighborhood
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
4 bedrooms, desk, iron/ironing board, travel cot

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

9.8 out of 10, Exceptional, (7)
"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!"
The price is €477
includes taxes & fees
19 Aug - 20 Aug
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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Top Greater Upper Marlboro Hotel Reviews

Hyatt Place Washington DC/National Mall

Hyatt Place Washington DC/National Mall

10/10 Excellent
"Property was very clean and staff was attentive to needs"
Holly 2-night trip
Posted 20 hours ago
Hyatt Place Washington DC/National Mall