Top Winter Vacations - Vacation Rentals in Plentywood

A newly executive basement apt From US $204
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Entire 3bedrooms 2bathrooms exquisite house From US $220
         

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7.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Winterton Suites From US $161
         

9.8 (76 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Entire 3br/2ba exquisite house From US $373
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Downtown 2BR - Fast WiFi-Easy Parking -Self Check-in From US $153
         

Clean, comfortable cabin. Sleeps 4 From US $163
         

9.8 (24 Reviews)
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cedar cabin. Fully equipped. Sleeps 3 comfortably. From US $166
         

9.6 (25 Reviews)
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Luxury Places to Stay in Plentywood

Over 76+ Luxury Places to Stay in or Near Plentywood
Hawthorn Suites by Wyndham Williston From US $350
         

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8.8 (322 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Holiday Inn Express and Suites Williston by IHG From US $179
         

Top-Rated Vacation Rentals with a Pool in Plentywood

Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Plentywood
Hampton Inn & Suites Williston From US $173
         

9.0 (235 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Williston Hotel & Suites From US $153
         

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8.8 (581 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express & Suites - Williston by IHG From US $126
         

8.4 (63 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Plus Williston Hotel & Suites From US $158
         

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7.9 (110 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Fairbridge Inn & Suites Williston Near Airport From US $84
         

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6.9 (222 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Grand Williston Hotel and Conference Center From US $116
         

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6.7 (131 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Old School Motel RV From US $59
         

5.3 (6 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Super 8 by Wyndham Williston ND From US $49
         

3.6 (112 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Plentywood

Over 18+ Pet-Friendly Vacation Rentals in or Near Plentywood
WoodSpring Suites Williston From US $50
         

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10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Clarion Hotel & Suites Williston From US $148
         

8.0 (111 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • TV
Really nice home one block off University Ave From US $136
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful farm home close to hunting, fishing and hiking From US $277
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 40ft 5th wheel From US $110
         

8.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Williston Apartment w/ Missouri River Views! From US $110
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
River Hacienda #1 - Private 2 Story Home with Missouri River View From US $90
         

8.6 (8 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Large Vacation Homes & Villas in Plentywood

Over 3+ Large Vacation Homes & Villas in or Near Plentywood
Econo Lodge Williston From US $79
         

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6.8 (22 Reviews)
Cabin
  • Parking
  • Guest Services
  • Child Friendly
5-bedroom house in Outlook n From US $243
         

New
House
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Plentywood

Over 22+ Wheelchair Accessible Vacation Homes in or Near Plentywood
Winterton Suites From US $145
         

9.4 (5 Reviews)
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Landmark Suites From US $154
         

9.4 (684 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Candlewood Suites Williston by IHG From US $151
         

9.3 (13 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Bakken Airport XWA Hotel & Studios From US $78
         

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9.0 (990 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Hampton Inn & Suites Williston From US $168
         

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8.8 (31 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
MainStay Suites Williston From US $132
         

8.8 (249 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Hawthorn Suites by Wyndham Williston From US $168
         

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8.7 (151 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Candlewood Suites Williston by IHG From US $169
         

8.8 (133 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Plentywood Vacation Rentals and Airbnb Places to Stay Under $200

Over 34+ Plentywood Vacation Rentals and Airbnb Places to Stay Under $200
Entire 4br and 2ba at center of Downtown From US $163
         

5.7 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Old School Motel RV From US $72
         

9.2 (19 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Cozy 1-bedroom apartment within walking distance of the Hospital. From US $176
         

Instantly Bookable Vacation Homes in Plentywood

Over 4+ Instantly Bookable Vacation Homes in or Near Plentywood
Renovated modern studio apartment in the heart of downtown. From US $316
         

About Plentywood Vacation Rentals

With more than 85 Plentywood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Plentywood.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Plentywood, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Plentywood. Places to stay near Plentywood are 298.68 ft² on average, with prices averaging US $161 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Plentywood with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Plentywood

Type Count
Hotels 46
Vacation Homes 24
Holiday Apartments 10
Cabin Rentals 4
Others 1

Use these Quick Filters to Find a Vacation Rental in Plentywood

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Plentywood.

Weather in Plentywood

View the weather forecast for Plentywood before booking your Plentywood Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Plentywood Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Plentywood?
Which vacation homes in Plentywood are best for families?

If you are looking for a family-friendly vacation home in Plentywood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Plentywood:

How many vacation rentals are available in Plentywood?

Currently, the total number of properties listed in 2026 is over 85 in the Plentywood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Plentywood.