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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester vacation rentals

A covered porch with wooden chairs and a bench, a 'Hello' sign, and a view of a grassy field.

1. RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS

RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS
Mounds
10.0 out of 10, Exceptional, (4 reviews)
"It was Great and host left us some welcome home treats. "
United States
Chadrick J.
The price is AED 698
AED 1,259 total
includes taxes & fees
31 Oct - 1 Nov
RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS
A room with a brick wall, a large window with curtains, a purple velvet sofa, a zebra-patterned rug, and a black ceiling fan.

2. Charming and unique upscale 1-bedroom apartment in downtown Okmulgee

Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
Okmulgee
The price is AED 506
AED 1,110 total
includes taxes & fees
1 Oct - 2 Oct
Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
Room

3. 1920s loft 1-bedroom apartment

1920s loft 1-bedroom apartment
Okmulgee
The price is AED 506
AED 897 total
includes taxes & fees
8 Oct - 9 Oct
1920s loft 1-bedroom apartment
A backyard with a curved concrete path, a stone building, and a fenced area with outdoor seating.

4. Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
South Tulsa
10.0 out of 10, Exceptional, (49 reviews)
"Very beautiful place with great host! "
United States
Mark M.
The price is AED 419
AED 588 total
includes taxes & fees
1 Oct - 2 Oct
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
A modern living room with a sectional sofa, ottoman, and a kitchen in the background.

5. Splash pad, Pool, & Catch and Release Pond

Splash pad, Pool, & Catch and Release Pond
Bixby
10.0 out of 10, Exceptional, (5 reviews)
"Very nice neighborhood and had plenty of room for us. We would definitely stay here again "
United States
DONNA S.
The price is AED 795
AED 2,020 total
includes taxes & fees
19 Oct - 20 Oct
Splash pad, Pool, & Catch and Release Pond
A spacious living room with a gray sofa, a brick fireplace, and a dining area with a table and chairs.

6. Breezy Two Bedroom in South Tulsa

Breezy Two Bedroom in South Tulsa
South Tulsa
9.2 out of 10, Wonderful, (21 reviews)
"Great location and clean."
United States
Amber B.
The price is AED 364
AED 951 total
includes taxes & fees
3 Oct - 4 Oct
Breezy Two Bedroom in South Tulsa
A spacious living area with a modern kitchen in the background, featuring wooden cabinets and a large decorative mirror.

7. Heart of Route 66. Stunning Apartment on Old City Hall's 2nd Floor

Heart of Route 66. Stunning Apartment on Old City Hall's 2nd Floor
Sapulpa
10.0 out of 10, Exceptional, (1 review)
"Beautiful location, beautiful apartment! We had a perfect stay, and hope to return. Thank you! "
United States
Ashley T.
Heart of Route 66. Stunning Apartment on Old City Hall's 2nd Floor
A backyard with a swimming pool, surrounded by a wooden deck and a fence.

8. 2 Bedroom 2 Bath Condo

2 Bedroom 2 Bath Condo
South Tulsa
9.6 out of 10, Exceptional, (5 reviews)
"Clean clean clean!Very welcoming and close to where I needed to be!"
United States
Rachael H.
The price is AED 455
AED 1,023 total
includes taxes & fees
1 Oct - 2 Oct
2 Bedroom 2 Bath Condo
A stationary train car with a rear door, parked on a gravel surface with trees in the background.

9. 1952 Royal Spartanette Trailer @ Teepee Drive-In

1952 Royal Spartanette Trailer @ Teepee Drive-In
Sapulpa
10.0 out of 10, Exceptional, (2 reviews)
"It was just a pit stop on our way home from Texas! We enjoyed the drive in and the cute trailer it was nice and clean and can not forget the smash burgers at the concession too. The host always answered any concerns."
United States
angela p.
1952 Royal Spartanette Trailer @ Teepee Drive-In
A modern kitchen with a wooden countertop, built-in shelves, and a staircase leading to another level.

10. 1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs

1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
Broken Arrow
9.6 out of 10, Exceptional, (5 reviews)
"Thank you again for hosting us. The farmhouse was a perfect fit for our family and exactly what we needed for a relaxing getaway. We especially loved gathering around the fire pit for our s’mores night—it made for such a fun memory. My in‑laws are still talking about how much they enjoyed the tour of the antique cars.We truly appreciated the hospitality and all the thoughtful touches. We’d be happy to stay again in the future."
United States
Sonny G.
The price is AED 384
AED 1,118 total
includes taxes & fees
19 Oct - 20 Oct
1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
A living room with a stone fireplace, a flat-screen TV mounted above it, a sofa, a coffee table, and a wicker chair.

11. The Fern Retreat - 3 Bedroom Duplex South Tulsa

The Fern Retreat - 3 Bedroom Duplex South Tulsa
South Tulsa
10.0 out of 10, Exceptional, (3 reviews)
"A nice place to stay. Very comfortable. Would recommend"
United States
Sue B.
The price is AED 382
AED 519 total
includes taxes & fees
4 Oct - 5 Oct
The Fern Retreat - 3 Bedroom Duplex South Tulsa
A residential house with a covered porch, a brick chimney, and a garden with various plants and flowers.

12. Jenks 5BR · Pond + Playground · Near Outlets

Jenks 5BR · Pond + Playground · Near Outlets
Jenks
8.0 out of 10, Very good, (2 reviews)
"Beautiful home and great hospitality from the owners! Highly recommend!"
United States
Derrell J.
Jenks 5BR · Pond + Playground · Near Outlets
A bedroom with a bed, a ceiling fan, a TV, a mirror, and a painting on the wall.

13. Sleeps 7~GarageAccess~Coffee Bar~Patio w/ FirePit

Sleeps 7~GarageAccess~Coffee Bar~Patio w/ FirePit
Bixby
The price is AED 364
AED 1,059 total
includes taxes & fees
4 Oct - 5 Oct
Sleeps 7~GarageAccess~Coffee Bar~Patio w/ FirePit
A white console table with a vase, a candle, and a framed quote.

14. Spacious Bixby Home w/ Fire Pit & Sleeps 12+

Spacious Bixby Home w/ Fire Pit & Sleeps 12+
Bixby
The price is AED 1,001
AED 2,198 total
includes taxes & fees
29 Oct - 30 Oct
Spacious Bixby Home w/ Fire Pit & Sleeps 12+
A modern kitchen with a brick wall, a wooden table, and chairs.

15. SPACIOUS 4 Bedroom in the Heart of Tulsa

SPACIOUS 4 Bedroom in the Heart of Tulsa
South Tulsa
9.0 out of 10, Wonderful, (9 reviews)
"Great place to stay with plenty of room. It's well cared for and comfortable. It also has a wonderful coffee bar. Also the people at Victory are amazing to work with/really good customerservice. We are loving our stay here."
United States
Becky J.
The price is AED 533
AED 1,151 total
includes taxes & fees
12 Oct - 13 Oct
SPACIOUS 4 Bedroom in the Heart of Tulsa
A modern kitchen with white cabinetry, stainless steel appliances, and a round dining table with chairs.

16. Brand New Modern Getaway on Private Land!

Brand New Modern Getaway on Private Land!
Tulsa
9.0 out of 10, Wonderful, (2 reviews)
"I really enjoyed my stay. This property is located on a lovely piece of land in a peaceful and quiet neighborhood. My side of the duplex was super clean and decorated very nicely. The host was responsive and super helpful (there was a glitch with the VRBO system, not the property). I would 100% book this property again. "
United States
David J.
The price is AED 235
AED 845 total
includes taxes & fees
11 Oct - 12 Oct
Brand New Modern Getaway on Private Land!
A living room with a foosball table, a green chair, a sofa, a fireplace, and a television on the wall.

17. Groovy Getaway - Retro Vibes and Modern Comfort

Groovy Getaway - Retro Vibes and Modern Comfort
South Tulsa
8.0 out of 10, Very good, (4 reviews)
"Wonderful place !"
United States
Carlo I.
Groovy Getaway - Retro Vibes and Modern Comfort
A bedroom with a bed, a mirror, a nightstand, and a wall with a geometric pattern.

18. Monochrone madness - Step into a coloring book getaway

Monochrone madness - Step into a coloring book getaway
South Tulsa
The price is AED 298
AED 695 total
includes taxes & fees
11 Oct - 12 Oct
Monochrone madness - Step into a coloring book getaway
A modern living room with a sofa, coffee table, and a TV. There is a fireplace and a ceiling fan.

19. Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub

Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
South Tulsa
9.4 out of 10, Exceptional, (14 reviews)
"Really neat place tucked away right along riverside parkway and Tulsa hills enjoyed are time here"
United States
brenen r.
The price is AED 387
AED 961 total
includes taxes & fees
5 Oct - 6 Oct
Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
A large, multi-story building with a red-tiled roof, a central courtyard with a fountain, and a well-maintained garden with various plants and rocks.

20. Paradise awaits. Southern Hills/ORU/River Spirit

Paradise awaits. Southern Hills/ORU/River Spirit
South Tulsa
9.4 out of 10, Exceptional, (16 reviews)
"We loved our stay here! The place was bigger than I expected and comfortably accommodated my family and I. It also had all the baby gear we needed for our infant."
United States
Valeria C.
The price is AED 582
AED 1,503 total
includes taxes & fees
1 Oct - 2 Oct
Paradise awaits. Southern Hills/ORU/River Spirit
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 Winchester Hotel Reviews

Holiday Inn Express & Suites Tulsa South - Woodland Hills by IHG

Holiday Inn Express & Suites Tulsa South - Woodland Hills by IHG

10/10 Excellent
"Very nice staff"
Kelly 1-night trip
Posted 8 hours ago
Holiday Inn Express & Suites Tulsa South - Woodland Hills by IHG

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals near top attractions in Winchester, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winchester has to offer?

4 bedrooms+Outdoor gazebo+Garage+office: This vacation home rental outside of Winchester offers a fireplace, a pool table, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

What’s there to see and do in Winchester?

Explore the area and family-friendly sights such as Oklahoma Aquarium, or get out into nature at a spot like Hawthorn Park. In the larger area, you’ll find Creek Council House Museum and Okmulgee State Park.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Winchester. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips.