Book Holiday Homes in Jennings

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Featured Holiday Homes in Jennings

Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly

Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly

Cushing OK
The price is AU$165 per night from 30 Dec to 31 Dec
AU$165
30 Dec - 31 Dec
includes taxes & fees
With a stay at this vacation home in Cushing, you'll be within a 5-minute drive of Memorial Park and Drumright Regional Hospital.
Opens in a new windowSerenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly
2-bedroom 1 bath Barndominium in Cushing- Country/Western/Music/Pet Friendly

2-bedroom 1 bath Barndominium in Cushing- Country/Western/Music/Pet Friendly

Cushing OK
The price is AU$176 per night from 17 Dec to 18 Dec
AU$176
17 Dec - 18 Dec
includes taxes & fees
With a stay at this vacation home in Cushing, you'll be within a 10-minute drive of Memorial Park and Drumright Regional Hospital.
Opens in a new window2-bedroom 1 bath Barndominium in Cushing- Country/Western/Music/Pet Friendly
Gorgeous country retreat with pond and pool!

Gorgeous country retreat with pond and pool!

Sand Springs OK
Located in Sand Springs, this vacation home is within a 5-minute drive of Keystone Lake and Shell Lake.
Opens in a new windowGorgeous country retreat with pond and pool!
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Quiet Country Home 3mins to Fairgrounds and 8 min to town - 1 acre 4 bedroom

Quiet Country Home 3mins to Fairgrounds and 8 min to town - 1 acre 4 bedroom

Stillwater OK
The price is AU$431 per night from 18 Dec to 19 Dec
AU$431
18 Dec - 19 Dec
includes taxes & fees
With a stay at this vacation home in Stillwater, you'll be within a 10-minute drive of Oklahoma State University and Payne County Expo Center.
Opens in a new windowQuiet Country Home 3mins to Fairgrounds and 8 min to town - 1 acre 4 bedroom
"Country Charm & Game Room Fun, Pool Table, Screens, & Xbox, Close to Stilly!"

"Country Charm & Game Room Fun, Pool Table, Screens, & Xbox, Close to Stilly!"

Glencoe OK
Located in Glencoe, this vacation home is in a rural location, within a 10-minute drive of Payne County Expo Center and White Barn Par 3 Golf.
Opens in a new window"Country Charm & Game Room Fun, Pool Table, Screens, & Xbox, Close to Stilly!"
Beautiful hideaway on Lake Keystone

Beautiful hideaway on Lake Keystone

Cleveland OK
Located in Cleveland, this vacation home is within a 5-minute drive of Keystone Lake and Arkansas River.
Opens in a new windowBeautiful hideaway on Lake Keystone
Cozy in the Country no 11% Stw tax

Cozy in the Country no 11% Stw tax

Stillwater OK
With a stay at this vacation home in Stillwater, you'll be within a 15-minute drive of Oklahoma State University and Payne County Expo Center.
Opens in a new windowCozy in the Country no 11% Stw tax
Ben Ranch Cabin #1 . Located in century old Pecan Orchard, historic Osage County

Ben Ranch Cabin #1 . Located in century old Pecan Orchard, historic Osage County

Ralston OK
When you stay at this vacation home in Ralston, you'll be on a river and 10 minutes by foot from Arkansas River.
Opens in a new windowBen Ranch Cabin #1 . Located in century old Pecan Orchard, historic Osage County
Historic Route 66 Hideaway

Historic Route 66 Hideaway

2 out of 5
Bristow OK
The price is AU$337 per night from 14 Jan to 15 Jan
AU$337
14 Jan - 15 Jan 2026
includes taxes & fees
With a stay at this vacation home in Bristow, you'll be 16.7 mi (26.9 km) from StableRidge Vineyards and 19.8 mi (31.9 km) from Lake Heyburn State Park.
Opens in a new windowHistoric Route 66 Hideaway
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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.

Jennings Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jennings vacation homes are the perfect way for you to wing it.

Holiday houses in Jennings let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jennings in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jennings adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jennings with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jennings vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jennings Holiday Homes essential information

Accommodation
19 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$431
Popular accommodation
Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly, 2-bedroom 1 bath Barndominium in Cushing- Country/Western/Music/Pet Friendly, Gorgeous country retreat with pond and pool! , Quiet Country Home 3mins to Fairgrounds and 8 min to town - 1 acre 4 bedroom, "Country Charm & Game Room Fun, Pool Table, Screens, & Xbox, Close to Stilly!", Beautiful hideaway on Lake Keystone, Cozy in the Country no 11% Stw tax, Ben Ranch Cabin #1 . Located in century old Pecan Orchard, historic Osage County, Historic Route 66 Hideaway

Top trending hotels in Jennings

The Track House at Hallett

The Track House at Hallett

Hallett OK
With a stay at this vacation home in Jennings, you'll be within a 15-minute drive of Hallett Motor Racing Circuit and Cleveland Area Hospital.
Opens in a new windowThe Track House at Hallett
Holiday Inn Express & Suites Tulsa West - Sand Springs by IHG

Holiday Inn Express & Suites Tulsa West - Sand Springs by IHG

3.5 out of 5
101 West Morrow Road Sand Springs OK
Fully refundable
The price is AU$228 per night from 14 Jan to 15 Jan
AU$228
14 Jan - 15 Jan 2026
includes taxes & fees
A stay at Holiday Inn Express & Suites Tulsa West - Sand Springs by IHG places you in the heart of Sand Springs, within a 10-minute drive of Gilcrease Museum ...
Opens in a new windowHoliday Inn Express & Suites Tulsa West - Sand Springs by IHG
Holiday Inn Express & Suites Cushing by IHG

Holiday Inn Express & Suites Cushing by IHG

2.5 out of 5
2201 E MAIN STREET Cushing OK
Fully refundable
The price is AU$138 per night from 15 Jan to 16 Jan
AU$138
15 Jan - 16 Jan 2026
includes taxes & fees
Located in Cushing, Holiday Inn Express & Suites Cushing by IHG is within a 5-minute drive of Drumright Regional Hospital and Hillcrest Hospital Cushing.
Opens in a new windowHoliday Inn Express & Suites Cushing by IHG
Save an average of 15% on thousands of hotels when you're signed in
Wilshire Inn

Wilshire Inn

2.5 out of 5
1720 East Main Street Cushing OK
Fully refundableReserve now, pay when you stay
Located in Cushing, Wilshire Inn is within a 5-minute drive of Drumright Regional Hospital and Hillcrest Hospital Cushing.
Opens in a new windowWilshire Inn
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.