Winchester Holiday Rentals from AU$202: Search Short-Term Rentals

Q: 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.

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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

Mounds

Chadrick J.

includes taxes & fees

30 Sept - 1 Oct

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

Okmulgee

includes taxes & fees

30 Sept - 1 Oct

3. 1920s loft 1-bedroom apartment

Okmulgee

includes taxes & fees

30 Sept - 1 Oct

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

South Tulsa

Mark M.

includes taxes & fees

30 Sept - 1 Oct

A modern living room with a sectional sofa, ottoman, and a kitchen in the background.

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

Bixby

DONNA S.

includes taxes & fees

19 Oct - 20 Oct

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

South Tulsa

Amber B.

includes taxes & fees

30 Sept - 1 Oct

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

Sapulpa

Ashley T.

includes taxes & fees

5 Oct - 6 Oct

A backyard with a swimming pool, surrounded by a wooden deck and a fence.

8. 2 Bedroom 2 Bath Condo

South Tulsa

Rachael H.

includes taxes & fees

30 Sept - 1 Oct

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

Sapulpa

angela p.

includes taxes & fees

7 Oct - 8 Oct

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

Broken Arrow

"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."

Sonny G.

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

South Tulsa

Sue B.

includes taxes & fees

12 Oct - 13 Oct

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

Derrell J.

includes taxes & fees

13 Oct - 14 Oct

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

Bixby

includes taxes & fees

4 Oct - 5 Oct

A white console table with a vase, a candle, and a framed quote.

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

Bixby

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with a brick wall, a wooden table, and chairs.

15. SPACIOUS 4 Bedroom in the Heart of Tulsa

South Tulsa

Becky J.

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a round dining table with chairs.

16. Brand New Modern Getaway on Private Land!

Tulsa

David J.

includes taxes & fees

11 Oct - 12 Oct

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

South Tulsa

Carlo I.

includes taxes & fees

30 Sept - 1 Oct

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

South Tulsa

includes taxes & fees

30 Sept - 1 Oct

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

South Tulsa

brenen r.

includes taxes & fees

5 Oct - 6 Oct

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

South Tulsa

Valeria C.

includes taxes & fees

30 Sept - 1 Oct

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Top Winchester Hotel Reviews

Hampton Inn & Suites Tulsa-Woodland Hills 71st-Memorial

10/10 Excellent

"Would stay again........."

Residence Inn by Marriott Tulsa South

8/10 Good

"Had to change rooms because TV did not work in the room I was given. Room was clean and well maintained. For the most part, staff was friendly. Breakfast was the typical scrambled eggs and sausage. Hotel stay was above average. Excellent location to resturants, movie theater, and shopping."

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, 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 favourite 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 depend 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 AU$202 per night. Entering your travel dates in the search wizard might find you 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.

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Check prices for these dates

Our top choices for Winchester holiday rentals

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

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

3. 1920s loft 1-bedroom apartment

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

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

6. Breezy Two Bedroom in South Tulsa

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

8. 2 Bedroom 2 Bath Condo

9. 1952 Royal Spartanette Trailer @ Teepee Drive-In

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

11. The Fern Retreat - 3 Bedroom Duplex South Tulsa

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

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

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

15. SPACIOUS 4 Bedroom in the Heart of Tulsa

16. Brand New Modern Getaway on Private Land!

17. Groovy Getaway - Retro Vibes and Modern Comfort

18. Monochrone madness - Step into a coloring book getaway

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

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

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

Hampton Inn & Suites Tulsa-Woodland Hills 71st-Memorial

Holiday Inn Express Hotel & Suites Jenks by IHG

SpringHill Suites by Marriott Tulsa at Tulsa Hills

Courtyard by Marriott Tulsa Woodland Hills

Fairfield Inn & Suites Tulsa South Medical District

Residence Inn by Marriott Tulsa South

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

Find out more about Winchester

Frequently asked questions

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