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Vacation rentals in Upper Marlboro, Maryland, United States

Kone Oasis- hot tub, pool, theater/game rm. image 1

Kone Oasis- hot tub, pool, theater/game rm. image 2

Kone Oasis- hot tub, pool, theater/game rm. image 3

Kone Oasis- hot tub, pool, theater/game rm. image 4

Kone Oasis- hot tub, pool, theater/game rm. image 5

Kone Oasis- hot tub, pool, theater/game rm.

3 bedrooms·1 bath

Upper Marlboro • Maryland

4.94(223 reviews)

$ 718,00 USD totaal voor 3 nachten

9–12 nov 2026

mid century through and through.

Hot tub for 6. 2nd heater used during winter months so the hot tub is kept 100 to 104 all year round. Jets most powerful when focused on a single row of seats at a time.

Extra large Connect Four game set up on the deck. The deck is lit and there is a seating.

MCM w/ Hottub + Firepit, mins to DC/Metro image 4

MCM w/ Hottub + Firepit, mins to DC/Metro image 5

MCM w/ Hottub + Firepit, mins to DC/Metro

4 bedrooms·1 bath

Cheverly • Maryland

4.93(168 reviews)

$ 488,00 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Private kitchen

3-bedroom house near DC

3 bedrooms·1 bath

Oxon Hill • Maryland

$ 750,00 USD totaal voor 3 nachten

8–11 nov 2026

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

Main living space.

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

3 bedrooms·2 baths

North Beach • Maryland

4.96(26 reviews)

$ 964,05 USD totaal voor 3 nachten

9–12 nov 2026

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

3 bedrooms·2 baths

North Beach • Maryland

5(250 reviews)

$ 575,55 USD $ 502,96 USD totaal voor 3 nachten

9–12 nov 2026

Welcome to beautiful North Beach!

Cozy fire pit patio with stylish seating and outdoor dining

Cozy fire pit patio with private fenced yard and stylish outdoor seating

Palm Haven in North Beach, MD

One of two bedrooms on the ground floor, this bedroom has a queen sized bed and en-suite bathroom.

Palm Haven in North Beach, MD

4 bedrooms·3 baths

North Beach • Maryland

5(198 reviews)

$ 1.047,30 USD $ 891,46 USD totaal voor 3 nachten

14–17 nov 2026

Majestic Murphy Point

Back yard launch

Front facing the bay

Kitchen/Dining open floor plan

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath

North Beach • Maryland

4.8(114 reviews)

$ 1.320,00 USD totaal voor 3 nachten

31 mrt – 3 apr 2027

Potomac Riverfront Estate — Haiku River House, Single-Level, Fort Washington MD

Haiku River House

Haiku River House

Haiku River House

Haiku River House

Haiku River House

5 bedrooms·5 baths

Fort Washington • Maryland

$ 1.918,75 USD $ 1.710,48 USD totaal voor 3 nachten

29 nov – 2 dec 2026

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2 bedrooms·2 baths

Silver Spring • Maryland

$ 986,79 USD totaal voor 3 nachten

8–11 nov 2026

Property grounds

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

5 bedrooms·2 baths

Silver Spring • Maryland

$ 1.174,00 USD totaal voor 3 nachten

11–14 nov 2026

The Landing is a waterfront vacation home with private pool, fire pit, and spacious yard. It is family-friendly with plenty of spaces to gather. Located near Annapolis, Kent Narrows, Easton, St. Michael’s, Naval Academy, and wedding venues.

Waterfront home in Kent Island - the perfect place to stay on your vacation to Maryland’s Eastern Shore.

Firepit by the water lets you enjoy s’mores durning your stay in Stevensville, MD.

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

Cathedral ceilings with natural wood light-up this waterfront living room. This room has a dining table for 10, sofa area with electric fireplace and 65" tv and the children's playroom.

Waterfront 5BR w/ Pool + Firepit on Kent Island!

5 bedrooms·3½ baths

Stevensville • Maryland

$ 2.452,00 USD totaal voor 3 nachten

8–11 nov 2026

Furnished 4BR Home | Workspace & Extended Stays image 1

Furnished 4BR Home | Workspace & Extended Stays image 2

Furnished 4BR Home | Workspace & Extended Stays image 3

Furnished 4BR Home | Workspace & Extended Stays image 4

Furnished 4BR Home | Workspace & Extended Stays image 5

Furnished 4BR Home | Workspace & Extended Stays

4 bedrooms·2 baths

Silver Spring • Maryland

5(2 reviews)

$ 916,00 USD totaal voor 4 nachten

8–12 nov 2026

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

4 bedrooms·4 baths

Bethesda • Maryland

$ 3.511,55 USD totaal voor 3 nachten

8–11 nov 2026

Upscale Bethesda Home • Pool, Piano & Bar

Bethesda Row restaurants, about a 15-minute walk. Photo: Payton Chung, CC BY 2.0

Upscale Bethesda Home • Pool, Piano & Bar

Glen Echo Park carousel, about 2 miles away. Photo: Cjfman, CC BY-SA 4.0

Upscale Bethesda Home • Pool, Piano & Bar

Upscale Bethesda Home • Pool, Piano & Bar

4 bedrooms·4 baths

Bethesda • Maryland

$ 3.063,50 USD totaal voor 3 nachten

8–11 nov 2026

Off The Chart Stays Cottage

living room at entrance with gas fireplace and smart tv

Kitchen and Living room

Off The Chart Stays

2 bedrooms·2 baths

Stevensville • Maryland

5(8 reviews)

$ 1.709,40 USD totaal voor 3 nachten

8–11 nov 2026

Black Walnut Cove

Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths

Tilghman Island • Maryland

$ 1.006,25 USD totaal voor 3 nachten

8–11 nov 2026

4-Bedroom Get-a-Away near DC Metro image 1

4-Bedroom Get-a-Away near DC Metro image 2

4-Bedroom Get-a-Away near DC Metro image 3

4-Bedroom Get-a-Away near DC Metro image 4

4-Bedroom Get-a-Away near DC Metro image 5

4-Bedroom Get-a-Away near DC Metro

4 bedrooms·2 baths

Silver Spring • Maryland

$ 1.800,00 USD totaal voor 3 nachten

8–11 nov 2026

Oasis at Charity’s Hope Farm Resort image 1

Fun with inflatables on the beautiful salt water pool with whirlpool jets.

Oasis at Charity’s Hope Farm Resort image 3

Horse trainer works with our miniature horse and pony.

Oasis at Charity’s Hope Farm Resort image 5

Oasis at Charity’s Hope Farm Resort

5 bedrooms·3 baths

La Plata • Maryland

4.94(36 reviews)

$ 3.008,00 USD $ 1.884,80 USD totaal voor 3 nachten

8–11 nov 2026

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

5 bedrooms·2 baths

Silver Spring • Maryland

$ 1.043,00 USD totaal voor 3 nachten

11–14 nov 2026

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

5 bedrooms·0 baths

Silver Spring • Maryland

Private Guest Suite in Columbia image 1

Private Guest Suite in Columbia image 2

Spacious king bedroom with a Pack ’n Play available upon request, making the suite comfortable and convenient for families traveling with a little one.

Private Guest Suite in Columbia image 4

Private Guest Suite in Columbia image 5

Private Guest Suite in Columbia

1 bedroom·1 bath

Columbia • Maryland

5(41 reviews)

$ 671,22 USD totaal voor 3 nachten

19–22 nov 2026

Escape to the Riverpoint, this unique house embodies the charm of a Swiss chalet A-Frame, complemented by a picturesque boathouse on the serene Canal of the Port Tobacco River.

The hot tub is tucked under the deck which offers privacy. End your day soaking in the hot tub that can fit up to 7 people.

The fire pit is next to the river and in the center of a sand area making it feel like a little beach.

The backyard is fully-fenced in so everyone can enjoy the backyard comfortably

Watch your favorite films on this 85” Google TV in the basement movie room.

5BR Riverfront A-Frame

5 bedrooms·4 baths

Port Tobacco • Maryland

$ 1.347,46 USD totaal voor 3 nachten

9–12 nov 2026

Cozy 5-Bed Retreat, Heated Spa

Elegant brick home with glowing entry and stunning autumn curb appeal

Convenient in-home laundry room with washer, dryer, iron, and folding space

Cozy 5-Bed Retreat, Heated Spa

this is the Blue Room. The Decour is inspired by grand millennial chinoiserie. Daylight above is a remote controlled fandelier for climate comfort.

Cozy 5-Bed Retreat, Heated Spa

5 bedrooms·3½ baths

Port Republic • Maryland

4.78(58 reviews)

$ 1.680,50 USD totaal voor 3 nachten

9–12 nov 2026

Property grounds

Private kitchen

Stylish 3BR/3BA Townhome in Crown Gaithersburg, Walk to Rio, Pool, & Restaurants

3 bedrooms·3 baths

Rockville • Maryland

5(4 reviews)

$ 760,00 USD totaal voor 3 nachten

8–11 nov 2026