Vacation Homes in Roosevelt County
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Vacation Homes in Roosevelt County

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Top cities in Roosevelt County

A large, rusted metal bridge with multiple arches spanning a highway.

Wolf Point

A covered bridge with a sign reading "Cumberland" and a sunset in the background.

Culbertson

Poplar

Froid

Bainville

Brockton

Reserve

Homestead

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Our top choices for Roosevelt County vacation homes

A wooden structure with a door, a cross symbol, and a crescent moon symbol.

A wooden barrel-shaped structure with a sloped roof, a door, and a small step leading up to it.

A modern living room with a dark wooden coffee table, a white vase with a plant, and a stack of white plates.

A water feature with a waterfall, a control panel, and a metal barrier.

1. Modern New 3BR Hot Tub & Sauna - Peaceful Getaway

Modern New 3BR Hot Tub & Sauna - Peaceful Getaway

Williston

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very clean and well furnished. Everything was as described and advertised."

Dillon S.

The price is AED 667

AED 667

AED 1,548 total

includes taxes & fees

15 Nov - 16 Nov

Modern New 3BR Hot Tub & Sauna - Peaceful Getaway

A kitchen with white cabinets, a built-in oven, a microwave, a sink, and a refrigerator.

A living room with a fireplace, a sofa, a television, and a staircase leading to another room.

A kitchen with a white refrigerator, wooden table, and chairs. There is a window with a view of trees.

A bedroom with a bed, a wooden door, and a carpeted floor.

2. Our cozy, 2 bedroom home offers a blend of comfort and charm!

Our cozy, 2 bedroom home offers a blend of comfort and charm!

Plentywood

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

"Perfect spot in Plentywood!"

Karen B.

Our cozy, 2 bedroom home offers a blend of comfort and charm!

A modern living room with a wooden coffee table, black leather sofa, and a flat-screen TV mounted on a wooden panel wall.

A modern living room with a flat-screen TV, brown sofas, a coffee table, and a potted plant.

A deck with wicker furniture, a table, and a grill.

A bedroom with a bed, bedside tables, a nightstand, a potted plant, and a closet.

3. Charming 4-bedroom house. NO ANIMALS.

Charming 4-bedroom house. NO ANIMALS.

Wolf Point

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Full family experience nice location"

Paula S.

The price is AED 742

AED 742

AED 1,515 total

includes taxes & fees

22 Nov - 23 Nov

Charming 4-bedroom house. NO ANIMALS.

A black entertainment unit with a fish tank, decorative vases, and plants.

A hallway with a white door, a potted plant, and a wall-mounted light fixture.

A bar area with a whiskey-themed decor, including posters and a coffee machine.

A wooden deck with a grill and chairs, a table, and a trash can.

4. Entire 3br/2ba exquisite house

Entire 3br/2ba exquisite house

Williston

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Better than advertised, great host with great communication. "

RANDY

The price is AED 1,221

AED 1,221

AED 1,767 total

includes taxes & fees

1 Dec - 2 Dec

Entire 3br/2ba exquisite house

A modern kitchen with white cabinets, a black countertop, and a central island. There is a dining table with chairs and a decorative bowl.

A modern kitchen with white cabinets, a black refrigerator, and a central island with a sink.

A neatly made bed with a grey headboard, two bedside tables with lamps, a decorative wall hanging, and a patterned rug.

A modern kitchen with white cabinets, a black countertop, and a stainless steel refrigerator.

5. Spacious 3BR Home | Fenced Yard | BBQ | Fast WiFi

Spacious 3BR Home | Fenced Yard | BBQ | Fast WiFi

Williston

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"It was my second time staying here and it was so clean and I had everything I needed!"

Wesley S.

Spacious 3BR Home | Fenced Yard | BBQ | Fast WiFi

A two-story house with a stone facade, a garage, and a porch with a white railing.

A modern living room with a flat-screen TV mounted on the wall, a fireplace, a dining area with a table and chairs, and a kitchen in the background.

A living room with leather sofas, a glass coffee table, and a patterned rug.

6. A newly executive basement apt

A newly executive basement apt

Williston

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Everything was great! The check in process was very easy and communication was quick and responsive! A comfortable place to stay!!!"

Crissa S.

A newly executive basement apt

An outdoor patio with a table and chairs, a barbecue grill, and a patterned rug.

A modern kitchen with wooden cabinets, a microwave, and a large window.

A kitchen with wooden cabinets, a dishwasher, a microwave, and a sink.

A compact living space with a kitchenette, a sofa, a dining table, and a painting on the wall.

7. Cozy Northeast Montana Retreat, Hunters Welcome

Cozy Northeast Montana Retreat, Hunters Welcome

Plentywood

Cozy Northeast Montana Retreat, Hunters Welcome

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 reviews in Roosevelt County

A hotel room with a bed, a desk, a chair, a desk lamp, a TV, a window, and a bathroom with a sink and mirror.

A hotel reception area with a coffee station, a refrigerator, and a display of framed pictures.

A reception desk with a wooden finish, a framed horse painting, a sign for 'Homestead Inn,' and a coffee station.

A kitchen with a coffee machine, a microwave, and a toaster. There is a dining area with a table and chairs.

Homestead Inn Wolf Point Hwy 2

Wolf Point

10/10 Excellent

Nice and clean place

raghuveer

Reviewed October 15, 2026Reviewed October 15, 2026

Homestead Inn Wolf Point Hwy 2

A compact kitchen with a refrigerator, a dining table with chairs, and a window with curtains.

A bathroom with a sink, mirror, toiletries, and a television in the background.

A kitchen with white cabinets, a black refrigerator, and a white stove.

A hotel room with two beds, a bedside table with a remote control, and a window with curtains.

Homestead Inn Extended Stay - 3 nights minimum

Wolf Point

8/10 Good

The room was clean. New floor. Good comfortable beds. AC kept room cool in 100 degree heat. Price was very reasonable. Shower had lots of hot water. Room was quiet even though located next to highway #2. The unit is isolated but lots of lights made it feel secure. I would stay here again. Met the maintenance man. Ex veteran, very nice.

Bill

Reviewed July 21, 2026Reviewed July 21, 2026

Homestead Inn Extended Stay - 3 nights minimum

A spacious kitchen with modern appliances, a dining area with a long table and chairs, and artwork on the walls.

A multi-story hotel with a prominent sign reading "Landmark Suites".

A hotel room with a bed, desk, chair, TV, and a wardrobe.

A hotel reception area with a computer desk, a telephone, a printer, and a monitor. There is a glass door leading to a lobby area with a seating area and a vending machine.

Landmark Suites

Williston

10/10 Excellent

Room was very nice and breakfast is just right. Staff were very friendly and helpful.

Anonymous traveler

Reviewed January 12, 2017Reviewed January 12, 2017

Landmark Suites

A compact kitchen area with a microwave, toaster, and coffee machine. There is a window providing a view of the outside, and a sink with a soap dispenser.

A reception area with a Baymont by Wyndham sign, two reception desks, a clock, a phone, and a small table with a bottle and tissues.

A modern building with a red and white facade, large windows, and a visible entrance.

A hotel room with a bed, a desk, a kitchenette, and a TV.

Baymont by Wyndham Williston

Williston

10/10 Excellent

Spent the first night of our vacation here, very clean, beds are comfortable, rooms are not outdated, great rates, wish all motels were like this.

Anonymous traveler

Reviewed June 25, 2019Reviewed June 25, 2019

Baymont by Wyndham Williston

A modern hotel with a prominent entrance, a covered outdoor area, and a landscaped driveway.

A buffet with various food items including fruits, vegetables, and desserts.

A spacious hotel lobby with leather sofas, armchairs, and a coffee table.

A spacious lobby with a stone fireplace, comfortable seating, and a television mounted on the wall.

Clarion Hotel & Suites Williston

Williston

10/10 Excellent

My second stay here. Love the location. No complaints will stay again next time I’m in town

Timothy

Reviewed August 10, 2026Reviewed August 10, 2026

Clarion Hotel & Suites Williston

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Flights from Deering (DRG) to Sidney (SDY)
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Vacation Homes in Roosevelt County

Change your mind

Treat yourself

Be picky

Top cities in Roosevelt County

Wolf Point

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Roosevelt County vacation homes

1. Modern New 3BR Hot Tub & Sauna - Peaceful Getaway

2. Our cozy, 2 bedroom home offers a blend of comfort and charm!

3. Charming 4-bedroom house. NO ANIMALS.

4. Entire 3br/2ba exquisite house

5. Spacious 3BR Home | Fenced Yard | BBQ | Fast WiFi

6. A newly executive basement apt

7. Cozy Northeast Montana Retreat, Hunters Welcome

Top reviews in Roosevelt County

Homestead Inn Wolf Point Hwy 2

10/10 Excellent

Explore a world of travel with Expedia