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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester vacation rentals

Terrace/patio

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, (3 reviews)
"It was Great and host left us some welcome home treats. "
United States
Chadrick J.
The price is ￥26,408
￥49,997 total
includes taxes & fees
Sep 8 - Sep 9
RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS
Interior

2. Downtown Okmulgee Aviator Apartment

Downtown Okmulgee Aviator Apartment
Okmulgee
9.0 out of 10, Wonderful, (2 reviews)
"The Aviator loft was the perfect spot for my friends coming to Okmulgee for an Okmulgee Main Street event. They loved it....the decor, the space, the amazing views of Downtown Okmulgee's Historic buildings. The location is ideal and within walking distance to locally owned restaurants and shops. Jackson, our host was so friendly and welcoming. I look forwarding to referring friends coming to Okmulgee to this incredible space."
United States
Margaret H.
The price is ￥21,956
￥47,135 total
includes taxes & fees
Aug 15 - Aug 16
Downtown Okmulgee Aviator Apartment
Living area

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

Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
Okmulgee
The price is ￥23,112
￥48,568 total
includes taxes & fees
Aug 16 - Aug 17
Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
Property grounds

4. 1952 Royal Spartanette Trailer @ Teepee Drive-In

1952 Royal Spartanette Trailer @ Teepee Drive-In
Sapulpa
10.0 out of 10, Exceptional, (1 review)
"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.
The price is ￥20,880
￥29,940 total
includes taxes & fees
Aug 19 - Aug 20
1952 Royal Spartanette Trailer @ Teepee Drive-In
Property grounds

5. 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, (47 reviews)
"Very beautiful place with great host! "
United States
Mark M.
The price is ￥21,199
￥28,945 total
includes taxes & fees
Aug 23 - Aug 24
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
TV

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

Splash pad, Pool, & Catch and Release Pond
Bixby
10.0 out of 10, Exceptional, (4 reviews)
"Very nice neighborhood and had plenty of room for us. We would definitely stay here again "
United States
DONNA S.
The price is ￥46,246
￥92,968 total
includes taxes & fees
Aug 26 - Aug 27
Splash pad, Pool, & Catch and Release Pond
Smart TV, DVD player

7. We're All Mad Here! - A Wonderland Escape in Tulsa

We're All Mad Here! - A Wonderland Escape in Tulsa
South Tulsa
9.4 out of 10, Exceptional, (11 reviews)
"We have never stayed in a themed home before but we were looking for something a little different and fun and this property checked all of the boxes. The home is dark and moody, but is to be expected with an Alice and Wonderland themed home. All the little details were very neat. The house was clean and the beds were comfy."
United States
Stephanie S.
The price is ￥15,939
￥45,799 total
includes taxes & fees
Aug 27 - Aug 28
We're All Mad Here! - A Wonderland Escape in Tulsa
Smart TV, DVD player, books

8. Breezy Two Bedroom in South Tulsa

Breezy Two Bedroom in South Tulsa
South Tulsa
9.0 out of 10, Wonderful, (18 reviews)
"Just as described"
United States
Melanie M.
The price is ￥15,788
￥40,804 total
includes taxes & fees
Aug 16 - Aug 17
Breezy Two Bedroom in South Tulsa
Coffee/tea maker, fridge, microwave, oven

9. "The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
South Tulsa
9.4 out of 10, Exceptional, (48 reviews)
"Great place to stay! Very quiet neighborhood. Great value!"
United States
Mitch L.
The price is ￥19,653
￥35,184 total
includes taxes & fees
Aug 16 - Aug 17
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
Private kitchen

10. 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 ￥10,201
￥36,198 total
includes taxes & fees
Sep 8 - Sep 9
Brand New Modern Getaway on Private Land!
Lobby

11. 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.
The price is ￥26,459
￥42,698 total
includes taxes & fees
Aug 16 - Aug 17
Heart of Route 66. Stunning Apartment on Old City Hall's 2nd Floor
Dining

12. Centrally Located with Backyard and parking

Centrally Located with Backyard and parking
Broken Arrow
The price is ￥16,993
￥42,385 total
includes taxes & fees
Sep 13 - Sep 14
Centrally Located with Backyard and parking
Coffee/tea maker, fridge, microwave, oven

13. Scandi Home by Turnpike - KING Bed, Fast WiFi

Scandi Home by Turnpike - KING Bed, Fast WiFi
Broken Arrow
10.0 out of 10, Exceptional, (9 reviews)
"Great place! Great communication from the Host. "
United States
Hannah B.
The price is ￥18,330
￥50,826 total
includes taxes & fees
Aug 24 - Aug 25
Scandi Home by Turnpike - KING Bed, Fast WiFi
Living area

14. Newly Built Modern Getaway on Private Acreage!

Newly Built Modern Getaway on Private Acreage!
Tulsa
10.0 out of 10, Exceptional, (6 reviews)
"Great place! Would definitely come back to this location!"
United States
Roger H.
The price is ￥19,127
￥47,796 total
includes taxes & fees
Sep 10 - Sep 11
Newly Built Modern Getaway on Private Acreage!
Coffee/tea maker, fridge, microwave, oven

15. 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 ￥16,656
￥49,325 total
includes taxes & fees
Aug 27 - Aug 28
1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
Smart TV, fireplace

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

Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
South Tulsa
9.6 out of 10, Exceptional, (12 reviews)
"Really neat place tucked away right along riverside parkway and Tulsa hills enjoyed are time here"
United States
brenen r.
The price is ￥18,339
￥44,041 total
includes taxes & fees
Aug 26 - Aug 27
Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

17. The Red Door on 66th - 3BR/2BA Duplex

The Red Door on 66th - 3BR/2BA Duplex
South Tulsa
10.0 out of 10, Exceptional, (2 reviews)
"The host was excellent with communication!! Lily made sure we had everything for the stay. The location was good for the event we were attending. The home was clean and comfortable. A good stay!"
United States
Sha M.
The price is ￥15,939
￥41,926 total
includes taxes & fees
Sep 2 - Sep 3
The Red Door on 66th - 3BR/2BA Duplex
Smart TV, DVD player, books

18. 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.
The price is ￥15,780
￥41,740 total
includes taxes & fees
Aug 27 - Aug 28
Groovy Getaway - Retro Vibes and Modern Comfort
Coffee/tea maker, fridge, microwave, oven

19. Turkey Mountain Bungalow - Walk to the Trails

Turkey Mountain Bungalow - Walk to the Trails
Tulsa
10.0 out of 10, Exceptional, (4 reviews)
"Super cute and stylish rental. Plenty of room for four people and close to so many things! Great place to stay! "
United States
Melanie R.
The price is ￥20,848
￥42,018 total
includes taxes & fees
Aug 18 - Aug 19
Turkey Mountain Bungalow - Walk to the Trails
Exterior

20. Comfortable Suite in Tulsa | FREE Breakfast + Fitness Center + Seasonal Outdoor Pool

Comfortable Suite in Tulsa | FREE Breakfast + Fitness Center + Seasonal Outdoor Pool
Tulsa
10.0 out of 10, Exceptional, (1 review)
"Good location"
United States
Gavin H.
The price is ￥19,006
￥25,560 total
includes taxes & fees
Aug 16 - Aug 17
Comfortable Suite in Tulsa | FREE Breakfast + Fitness Center + Seasonal Outdoor Pool
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

River Spirit Casino Resort

River Spirit Casino Resort

10/10 Excellent
"Love the hotel, casino and especially the pool."
Melinda 3-night trip
Posted 10 hours ago
River Spirit Casino Resort

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool: This vacation home rental outside of Winchester offers an outdoor pool, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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 Oklahoma State University Institute of Technology and Creek Council House Museum.

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.