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Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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, (4 reviews)
"It was Great and host left us some welcome home treats. "
United States
Chadrick J.
The price is €293
includes taxes & fees
15 Nov - 16 Nov
RANCH 3BRHOUSE & BARN. HORSE&PET FRIENDLY. GATED. SLEEPS 7. GLENPOOL CITY LIMITS
A bedroom with a bed, a ceiling fan, a TV, a mirror, and a painting on the wall.

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

Sleeps 7~GarageAccess~Coffee Bar~Patio w/ FirePit
Bixby
Sleeps 7~GarageAccess~Coffee Bar~Patio w/ FirePit
A bedroom with a bed, a mirror, a nightstand, and a wall with a geometric pattern.

3. 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 €173
includes taxes & fees
17 Oct - 18 Oct
Monochrone madness - Step into a coloring book getaway
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, (51 reviews)
"Very beautiful place with great host! "
United States
Mark M.
The price is €147
includes taxes & fees
19 Oct - 20 Oct
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
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)
The price is €207
includes taxes & fees
2 Nov - 3 Nov
Blue Ember Retreat | 3BR, 2BA & Local Coffee
A modern kitchen with white cabinetry, stainless steel appliances, and a round dining table with chairs.

6. 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.
Brand New Modern Getaway on Private Land!
A stationary train car with a rear door, parked on a gravel surface with trees in the background.

7. 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 €170
includes taxes & fees
28 Oct - 29 Oct
1952 Royal Spartanette Trailer @ Teepee Drive-In
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.

8. 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 €269
includes taxes & fees
29 Oct - 30 Oct
Newly Built Modern Getaway on Private Acreage!
A spacious living room with a gray sofa, a brick fireplace, and a dining area with a table and chairs.

9. Breezy Two Bedroom in South Tulsa

Breezy Two Bedroom in South Tulsa
South Tulsa
9.0 out of 10, Wonderful, (22 reviews)
"Great location and clean."
United States
Amber B.
The price is €236
includes taxes & fees
18 Oct - 19 Oct
Breezy Two Bedroom in South Tulsa
A bedroom with a large bed, a ceiling fan, a window with blinds, a dresser, and a painting on the wall.

10. 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 €235
includes taxes & fees
16 Nov - 17 Nov
The Red Door on 66th - 3BR/2BA Duplex
A living room with a fireplace, a checkered rug, and a leather sofa.

11. 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 €260
includes taxes & fees
18 Oct - 19 Oct
We're All Mad Here! - A Wonderland Escape in Tulsa
A living room with a sofa, a coffee table, a painting, and a door.

12. Pastel Place | Colorful 3BR Tulsa Duplex

Pastel Place | Colorful 3BR Tulsa Duplex
South Tulsa
Pastel Place | Colorful 3BR Tulsa Duplex
A living room with a stone fireplace, a flat-screen TV mounted above it, a grey sofa, and a coffee table.

13. 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.
Juniper Retreat | 2BR, 2BA & Local Coffee
A bedroom with a bed, a ceiling fan, a window with curtains, and two framed pictures on the wall.

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

The Grove on 66th- 3B 2Bth Tulsa Duplex
South Tulsa
The price is €207
includes taxes & fees
18 Oct - 19 Oct
The Grove on 66th- 3B 2Bth Tulsa Duplex
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
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 sofa, a coffee table, and a wicker chair.

16. 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 €255
includes taxes & fees
1 Nov - 2 Nov
The Fern Retreat - 3 Bedroom Duplex South Tulsa
A backyard with a hot tub, wooden deck, outdoor furniture, and a barbecue grill.

17. 2600ft–7 Beds~Games~Toys~Desks

2600ft–7 Beds~Games~Toys~Desks
Broken Arrow
The price is €342
includes taxes & fees
26 Oct - 27 Oct
2600ft–7 Beds~Games~Toys~Desks
A living room with a foosball table, a green chair, a sofa, a fireplace, and a television on the wall.

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 €233
includes taxes & fees
16 Nov - 17 Nov
Groovy Getaway - Retro Vibes and Modern Comfort
An outdoor patio with a fire pit, wooden chairs, and a stone pillar.

19. Modern Country Retreat w/ outdoor fire pit! Newly remodeled~Sleeps 9~board games

Modern Country Retreat w/ outdoor fire pit! Newly remodeled~Sleeps 9~board games
Broken Arrow
10.0 out of 10, Exceptional, (1 review)
"Great property for a great price. Quiet area and plenty of space. Perfect for a large group of people. Host was very quick to respond. We had 3 different couples and all felt like we had our own spaces."
United States
Mason A.
The price is €369
includes taxes & fees
29 Oct - 30 Oct
Modern Country Retreat w/ outdoor fire pit! Newly remodeled~Sleeps 9~board games
A living room with a stone fireplace, a flat-screen TV above it, and a round coffee table.

20. 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.
Enjoy Comfort On 66th
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 Hotel & Suites Tulsa South by IHG

Holiday Inn Hotel & Suites Tulsa South by IHG

10/10 Excellent
"Comfortable bed & loved the suite."
Betty 1-night trip
Posted 1 day ago
Holiday Inn Hotel & Suites Tulsa South by IHG

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €144 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.