Winters Vacations Rentals - Vacation Rentals in Jennings

The Bunkhouse at Rolling Meadows Ranch w/Grill! From US $209
         

9.8 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Bunkhouse at Rolling Meadows Ranch with Grill! From US $235
         

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6.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Holiday Inn Express & Suites Cushing by IHG From US $107
         

9.4 (82 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Beautiful hideaway on Lake Keystone From US $276
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Track House at Hallett From US $368
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming cabin with AC and WiFi in delightful Cleveland From US $261
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Luxury Places to Stay in Jennings

Over 63+ Luxury Places to Stay in or Near Jennings
Pickleball Skyline Paradise | Keystone Lake | 3.5 Acre Oasis From US $1,227
         

Waterfront Keystone Lake Gem Private Dock, Kayaks From US $351
         

Nature Paradise at Keystone Lake From US $341
         

9.6 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront House at Keystone Lake (Sauna & More) From US $295
         

Waterfront Keystone Lake Gem: Private Dock, Kayaks From US $288
         

Top-Rated Vacation Rentals with a Pool in Jennings

Over 4+ Top-Rated Vacation Rentals with a Pool in or Near Jennings
Holiday Inn Express & Suites Cushing by IHG From US $109
         

9.4 (27 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Cushing Inn & Suites From US $116
         

8.2 (345 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Cushing Inn & Suites From US $115
         

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7.6 (57 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Jennings

Over 24+ Pet-Friendly Vacation Rentals in or Near Jennings
Cozy Lakeside Cabin, Mannford From US $156
         

9.8 (33 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Boomtown Inn From US $55
         

6.7 (62 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Track House at Hallett From US $564
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
1920’s Bootlegger Inn. 2-bedroom house with WiFi, AC in peaceful Cushing From US $118
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Lakeside Cabin From US $136
         

9.6 (74 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Cabin in front of the lake! From US $182
         

9.4 (117 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Jennings on PetFriendly.io

Large Vacation Homes & Villas in Jennings

Over 10+ Large Vacation Homes & Villas in or Near Jennings
Waterfront Keystone Lake House w/Shared Dock! From US $493
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Fairway Greensn From US $374
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Lake-View Sand Springs Haven: Outdoor Shower! From US $403
         

5.0 (1 Review)
House
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Charming, spacious 4-bedroom house in Cushing From US $226
         

New
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Wheelchair Accessible Vacation Homes in Jennings

Over 2+ Wheelchair Accessible Vacation Homes in or Near Jennings
Victorian Inn From US $90
         

6.4 (44 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Oasis Extended Stay From US $75
         

7.4 (24 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Jennings Vacation Rentals and Airbnb Places to Stay Under $200

Over 25+ Jennings Vacation Rentals and Airbnb Places to Stay Under $200
Happy place camper From US $128
         

10.0 (1 Review)
RV Rental
  • Air Conditioner
  • TV
  • Security/Safety
Executive Inn & Suites Cushing From US $77
         

6.9 (77 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Boomtown Inn From US $97
         

8.4 (97 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Cozy cabin loft located within Pier 51 Marina From US $175
         

5.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Lazy Spring Farm Star Gazing Hot Tub From US $136
         

New
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Instantly Bookable Vacation Homes in Jennings

Over 12+ Instantly Bookable Vacation Homes in or Near Jennings
Clean, Relaxing Camper In The Pawnee Countryside. From US $73
         

2bedroom 1bath Little home at Keystone Lake From US $68
         

About Jennings Vacation Rentals

With more than 72 Jennings vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wintersvacationsrentals 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 Jennings.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wintersvacationsrentals Jennings, 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 Jennings. Places to stay near Jennings are 486.14 ft² on average, with prices averaging US $243 a night.

Wintersvacationsrentals makes it easy and safe to find and compare vacation rentals in Jennings 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 Jennings

Type Count
Vacation Homes 48
Hotels 14
Cabin Rentals 6
Holiday Apartments 3

Use these Quick Filters to Find a Vacation Rental in Jennings

Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals 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 Jennings.

Weather in Jennings

View the weather forecast for Jennings before booking your Jennings 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

Jennings Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Jennings?
How many vacation rentals are available in Jennings?

Currently, the total number of properties listed in 2026 is over 72 in the Jennings area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Jennings.