Default HTG hotel image

Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester holiday 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, (5 reviews)
"It was Great and host left us some welcome home treats. "
United States
Chadrick J.
The price is HK$1,341
HK$2,579 total
includes taxes & fees
27 Oct - 28 Oct
RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS
A living room with a sofa, a coffee table, a painting, and a door.

2. Pastel Place | Colorful 3BR Tulsa Duplex

Pastel Place | Colorful 3BR Tulsa Duplex
South Tulsa
The price is HK$510
HK$1,665 total
includes taxes & fees
25 Oct - 26 Oct
Pastel Place | Colorful 3BR Tulsa Duplex
A modern living room with a stone fireplace, a flat-screen TV mounted above it, a round coffee table with a plant, and a grey sofa with cushions.

3. The Grove on 66th- 3B 2Bth Tulsa Duplex

The Grove on 66th- 3B 2Bth Tulsa Duplex
South Tulsa
The price is HK$510
HK$1,606 total
includes taxes & fees
25 Oct - 26 Oct
The Grove on 66th- 3B 2Bth Tulsa Duplex
A stationary train car with a rear door, parked on a gravel surface with trees in the background.

4. 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.
The price is HK$1,027
HK$1,465 total
includes taxes & fees
28 Oct - 29 Oct
1952 Royal Spartanette Trailer @ Teepee Drive-In
A living room with a sofa, a coffee table, and a painting on the wall.

5. Blue Ember Retreat | 3BR, 2BA & Local Coffee

Blue Ember Retreat | 3BR, 2BA & Local Coffee
South Tulsa
10.0 out of 10, Exceptional, (2 reviews)
"It was in a good location. Easy to get to. There’s no garage access but you have the whole house. This is a duplex, not a single family home in case you didn’t know. The stay was good. No issues."
United States
bryan e.
The price is HK$431
HK$1,597 total
includes taxes & fees
1 Nov - 2 Nov
Blue Ember Retreat | 3BR, 2BA & Local Coffee
A backyard with a curved concrete path, a stone building, and a fenced area with outdoor seating.

6. 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, (52 reviews)
"Very beautiful place with great host! "
United States
Mark M.
The price is HK$894
HK$1,255 total
includes taxes & fees
25 Oct - 26 Oct
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
A modern kitchen with white cabinetry, stainless steel appliances, and a round dining table with chairs.

7. 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 HK$502
HK$1,812 total
includes taxes & fees
26 Oct - 27 Oct
Brand New Modern Getaway on Private Land!
A bedroom with a large bed, a ceiling fan, a window with blinds, a dresser, and a painting on the wall.

8. 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 HK$627
HK$1,847 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door on 66th - 3BR/2BA Duplex
A spacious living area with a modern kitchen in the background, featuring wooden cabinets and a large decorative mirror.

9. 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 HK$1,302
HK$2,093 total
includes taxes & fees
30 Oct - 31 Oct
Heart of Route 66. Stunning Apartment on Old City Hall's 2nd Floor
A bedroom with a bed, a mirror, a nightstand, and a wall with a geometric pattern.

10. Monochrone madness - Step into a coloring book getaway

Monochrone madness - Step into a coloring book getaway
South Tulsa
10.0 out of 10, Exceptional, (1 review)
"The creative design and attention to detail throughout this property was simply amazing. Every single surface and object in the apartment was custom finished by hand to deliver on the promise of "Monochrome Madness". If you ever wondered what it would be like to live inside of a work of art, this is the way to experience it. I continued to find new, fun, and surprising design details throughout my stay."
United States
Anonymous traveller
The price is HK$635
HK$1,484 total
includes taxes & fees
28 Oct - 29 Oct
Monochrone madness - Step into a coloring book getaway
A living room with a stone fireplace, a flat-screen TV above it, and a round coffee table.

11. Enjoy Comfort On 66th

Enjoy Comfort On 66th
South Tulsa
7.8 out of 10, Good, (9 reviews)
"Property was clean and functional but very bare bones with a lot of deferred maintenance.If you just need a comfortable place to sleep this is fine but don't expect to be charmed."
United States
Tom S.
The price is HK$447
HK$1,859 total
includes taxes & fees
2 Nov - 3 Nov
Enjoy Comfort On 66th
A modern kitchen with white cabinets, a stainless steel refrigerator, and a built-in oven. There are two bar stools and a black sofa with red and gray cushions. A black and white rug is on the floor, and a window with a view of greenery is visible.

12. Newly Built Modern Getaway on Private Acreage!

Newly Built Modern Getaway on Private Acreage!
Tulsa
10.0 out of 10, Exceptional, (11 reviews)
"Great place! Would definitely come back to this location!"
United States
Roger H.
The price is HK$847
HK$2,218 total
includes taxes & fees
25 Oct - 26 Oct
Newly Built Modern Getaway on Private Acreage!
A modern living room with a sectional sofa, ottoman, and a kitchen in the background.

13. 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 HK$1,494
HK$4,058 total
includes taxes & fees
9 Nov - 10 Nov
Splash pad, Pool, & Catch and Release Pond
A living room with a foosball table, a green chair, a sofa, a fireplace, and a television on the wall.

14. 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 HK$620
HK$1,824 total
includes taxes & fees
25 Oct - 26 Oct
Groovy Getaway - Retro Vibes and Modern Comfort
A modern living room with a sofa, coffee table, and a TV. There is a fireplace and a ceiling fan.

15. 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, (15 reviews)
"I liked the lay out of the place, very cozy!"
United States
Christian
The price is HK$826
HK$2,068 total
includes taxes & fees
26 Oct - 27 Oct
Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
A living room with a stone fireplace, a flat-screen TV mounted above it, a grey sofa, and a coffee table.

16. Juniper Retreat | 2BR, 2BA & Local Coffee

Juniper Retreat | 2BR, 2BA & Local Coffee
South Tulsa
10.0 out of 10, Exceptional, (1 review)
"Amazing all around"
United States
JazzE E.
The price is HK$416
HK$1,563 total
includes taxes & fees
9 Nov - 10 Nov
Juniper Retreat | 2BR, 2BA & Local Coffee
A living room with a stone fireplace, a flat-screen TV mounted above it, a sofa, a coffee table, and a wicker chair.

17. The Fern Retreat - 3 Bedroom Duplex South Tulsa

The Fern Retreat - 3 Bedroom Duplex South Tulsa
South Tulsa
8.4 out of 10, Very good, (5 reviews)
The price is HK$627
HK$2,055 total
includes taxes & fees
1 Nov - 2 Nov
The Fern Retreat - 3 Bedroom Duplex South Tulsa
A house with a porch, a dining area, and a front yard with plants and a bird feeder.

18. Charming 2-Bedroom Bungalow: Historic Route 66 & Crossroads of America!

Charming 2-Bedroom Bungalow: Historic Route 66 & Crossroads of America!
Sapulpa
10.0 out of 10, Exceptional, (12 reviews)
"Great Stay"
United States
Jennifer T.
The price is HK$1,136
HK$2,612 total
includes taxes & fees
1 Nov - 2 Nov
Charming 2-Bedroom Bungalow: Historic Route 66 & Crossroads of America!
A living room with a fireplace, a checkered rug, and a leather sofa.

19. 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 HK$627
HK$2,055 total
includes taxes & fees
1 Nov - 2 Nov
We're All Mad Here! - A Wonderland Escape in Tulsa
A living room with a sofa, armchair, coffee table, fireplace, and artwork on the wall.

20. The Greyline Getaway- 3B2Bth with Fenced Backyard

The Greyline Getaway- 3B2Bth with Fenced Backyard
South Tulsa
6.0 out of 10, (3 reviews)
"The home overall needs a good scrub down. Lock your valuables away lock your cars. The area is so so."
United States
Daniel I.
The price is HK$627
HK$1,833 total
includes taxes & fees
25 Oct - 26 Oct
The Greyline Getaway- 3B2Bth with Fenced Backyard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

River Spirit Casino Resort

River Spirit Casino Resort

10/10 Excellent
"Awesome friendly staff and the room service food provided by their on-site restaurant Fireside Grill was so delicious. Rooms were clean and nice, bed was comfortable."
Ellen 2-night trip
Posted 1 hour 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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

4 bedrooms+Outdoor gazebo+Garage+office: This holiday home rental outside of Winchester offers a fireplace, a pool table and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 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 wider area, you’ll find Creek Council House Museum and Okmulgee State Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.