Search Greater Upper Marlboro Cottage Accommodations

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Greater Upper Marlboro

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (48)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (92)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Lovely backyard cottage with easy access to metro, shops, dining!
Enjoy cooking in this well-lit kitchen with a sleek island and stainless steel appliances.

Lovely backyard cottage with easy access to metro, shops, dining!

10.0 out of 10, Exceptional, (67)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!
Updated North Beach Cottage: Pet Friendly!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large island, and a sink.

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Perfect location for USNA Commissioning Week
Relax in this open-plan living area featuring a central island, dining space, and comfortable seating.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Enjoy a serene lakeside escape with a picnic table and access to a pebbly beach.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$467
includes taxes & fees
29 July - 30 July
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Relax in a serene outdoor space surrounded by lush greenery and trees, featuring a fire pit and comfortable seating.

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (1)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Situated by a serene body of water, this bench offers a tranquil view of the surrounding shoreline.

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (29)
"Tranquil cottage by the river to relax and reconnect for couples. Quick drive to Annapolis mall and downtown. Lots of outdoor seating to enjoy. Hosts were very responsive to our questions and request for bikes. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Enjoy cooking in this well-equipped kitchen with a dishwasher and convenient access to the outdoors.

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

10.0 out of 10, Exceptional, (20)
"We were very pleased with the location including its proximity to the sites and the neighborhood. Fran was very kind and responsive during our stay. "
The price is AU$545
includes taxes & fees
17 Aug - 18 Aug
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Relax by the pool surrounded by lounge chairs and outdoor seating.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Situated in a serene, environment, this charming house offers a welcoming entrance and a tranquil atmosphere.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (212)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
The Yellow Cottage on Harness Creek
Traditional house with a front porch surrounded by lush gardens and flowering plants.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (160)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
North Beach Cottage - Walk to Chesapeake Bay
Enjoy a game of pool in this room with a pool table and expansive views of the backyard through large windows.

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Enjoy serene sunsets over a peaceful lake or sea from a tranquil beach with a tree and rocks.

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove.

Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!

9.8 out of 10, Exceptional, (7)
"We had a great week in DC and this house worked out perfectly. If I needed anything Courtney was quick to respond on VRBO message page. Would definitely consider this house again if we were to return.Thank you Courtney!"
Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!
9 Mi to National Mall: Spacious Bethesda Retreat!
Relax in this stylish living room with a large flat-screen TV, two sofas, and a glass coffee table.

9 Mi to National Mall: Spacious Bethesda Retreat!

3.0 star property
9 Mi to National Mall: Spacious Bethesda Retreat!
1 Mi to Old Town: Historic Area Gem in Alexandria
Enjoy dining in style with a beautifully set table and comfortable seating.

1 Mi to Old Town: Historic Area Gem in Alexandria

3.0 star property
2.0 out of 10, (1)
"Everywhere dirtincluding the bath rooms. All full off old stuff."
1 Mi to Old Town: Historic Area Gem in Alexandria
New Home w Luxe King Suite, Porch Vibes & Parking
Enjoy cooking in this well-lit kitchen with a large stove, oven, and ample storage.

New Home w Luxe King Suite, Porch Vibes & Parking

New Home w Luxe King Suite, Porch Vibes & Parking
Walk to Everything - Historic Art’s District
Stroll along the garden pathway to the front door of this charming home, surrounded by lush greenery and flowering plants.

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District
Enchanting West River Retreat
Relax on the waterfront patio with a clear view of the marina and comfortable seating.

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Convenient enough and out of the way enough to enjoy Annapolis for the weekend. Well appointed and comfortable for the four of us. "
Enchanting West River Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free