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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winchester vacation rentals

Smart TV

Juniper Retreat | 2BR, 2BA & Local Coffee

Juniper Retreat | 2BR, 2BA & Local Coffee
South Tulsa
$192 nightly
The price is $214
Jul 19 - Jul 20
Total with taxes and fees
Juniper Retreat | 2BR, 2BA & Local Coffee
Smart TV

Pastel Place | Colorful 3BR Tulsa Duplex

Pastel Place | Colorful 3BR Tulsa Duplex
South Tulsa
$216 nightly
The price is $241
Jul 19 - Jul 20
Total with taxes and fees
Pastel Place | Colorful 3BR Tulsa Duplex
Smart TV

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

Blue Ember Retreat | 3BR, 2BA & Local Coffee
South Tulsa
$211 nightly
The price is $236
Aug 3 - Aug 4
Total with taxes and fees
Blue Ember Retreat | 3BR, 2BA & Local Coffee
WiFi, bed sheets

1920s loft 1-bedroom apartment

1920s loft 1-bedroom apartment
Okmulgee
$216 nightly
The price is $235
Jul 19 - Jul 20
Total with taxes and fees
1920s loft 1-bedroom apartment
Private kitchen

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.
$215 nightly
The price is $231
Jul 20 - Jul 21
Total with taxes and fees
Brand New Modern Getaway on Private Land!
Coffee/tea maker, fridge, microwave, oven

"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, (46 reviews)
"This home was a great location and comfortable setting for our quick stay in Tulsa. Host was quick to accommodate a last minute request and we were happy to enjoy this property."
United States
Adam C.
$193 nightly
The price is $217
Jul 19 - Jul 20
Total with taxes and fees
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
Property grounds

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, (43 reviews)
"Perfect place to stay over night. Great central location and very comfortable."
United States
John L.
$168 nightly
The price is $181
Jul 19 - Jul 20
Total with taxes and fees
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
Living area

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.
$277 nightly
The price is $298
Aug 2 - Aug 3
Total with taxes and fees
Newly Built Modern Getaway on Private Acreage!
Coffee/tea maker, fridge, microwave, oven

5 star single level home, 4 bdrm, 3 bath + private office and great backyard!

5 star single level home, 4 bdrm, 3 bath + private office and great backyard!
Bixby
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful house very clean. Plenty of parking, but my truck did not fit in garage. That was not a game changer for me. Good places close to eat. Thank you "
United States
Richard H.
5 star single level home, 4 bdrm, 3 bath + private office and great backyard!
Coffee/tea maker, fridge, microwave, oven

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

1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
Broken Arrow
9.4 out of 10, Exceptional, (3 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.
$284 nightly
The price is $307
Jul 20 - Jul 21
Total with taxes and fees
1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
Iron/ironing board, travel crib, WiFi (free), bed sheets

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

The Red Door on 66th - 3BR/2BA Duplex
South Tulsa
10.0 out of 10, Exceptional, (1 review)
"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.
$233 nightly
The price is $260
Jul 19 - Jul 20
Total with taxes and fees
The Red Door on 66th - 3BR/2BA Duplex
Coffee/tea maker, fridge, microwave, oven

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.
$210 nightly
The price is $235
Jul 20 - Jul 21
Total with taxes and fees
Turkey Mountain Bungalow - Walk to the Trails
Dining

Beautifully Remodeled 3-Bedroom Cozy Home!!

Beautifully Remodeled 3-Bedroom Cozy Home!!
Broken Arrow
9.6 out of 10, Exceptional, (58 reviews)
"We had a wonderful stay here and the host was delightful! Will stay again if we are in the area! "
United States
Lauren R.
$256 nightly
The price is $275
Jul 25 - Jul 26
Total with taxes and fees
Beautifully Remodeled 3-Bedroom Cozy Home!!
Interior

King Suite-4 Bedroom-Brookside-Riverside

King Suite-4 Bedroom-Brookside-Riverside
South Tulsa
9.2 out of 10, Wonderful, (15 reviews)
"Yes the stay was awesome!"
United States
Gavin H.
$311 nightly
The price is $335
Aug 4 - Aug 5
Total with taxes and fees
King Suite-4 Bedroom-Brookside-Riverside
Property grounds

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.
$198 nightly
The price is $208
Jul 19 - Jul 20
Total with taxes and fees
1952 Royal Spartanette Trailer @ Teepee Drive-In
Exterior

Spacious Beautiful Modern Updated 4 BR 2.5 Bath in a South Tulsa neighborhood.

Spacious Beautiful Modern Updated 4 BR 2.5 Bath in a South Tulsa neighborhood.
South Tulsa
10.0 out of 10, Exceptional, (6 reviews)
"House was perfect and host responded promptly!"
United States
Randi S.
$274 nightly
The price is $294
Jul 26 - Jul 27
Total with taxes and fees
Spacious Beautiful Modern Updated 4 BR 2.5 Bath in a South Tulsa neighborhood.
Smart TV, DVD player

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)
"THE ALICE AND WONDERLAND THEME WAS CUTE AND A EXPERIENCE. COMFY BED. QUITE NEIGHBORHOOD, CLOSE TO EVERYTHING"
United States
Phyllis E.
$247 nightly
The price is $276
Aug 2 - Aug 3
Total with taxes and fees
We're All Mad Here! - A Wonderland Escape in Tulsa
Dining

SPACIOUS 4 Bedroom in the Heart of Tulsa

SPACIOUS 4 Bedroom in the Heart of Tulsa
South Tulsa
8.8 out of 10, Excellent, (8 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.
$256 nightly
The price is $285
Jul 19 - Jul 20
Total with taxes and fees
SPACIOUS 4 Bedroom in the Heart of Tulsa
Smart TV, DVD player, books

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.
$232 nightly
The price is $259
Jul 19 - Jul 20
Total with taxes and fees
Groovy Getaway - Retro Vibes and Modern Comfort
Smart TV, DVD player, books

Breezy Two Bedroom in South Tulsa

Breezy Two Bedroom in South Tulsa
South Tulsa
9.0 out of 10, Wonderful, (17 reviews)
"Just as described"
United States
Melanie M.
$225 nightly
The price is $252
Jul 19 - Jul 20
Total with taxes and fees
Breezy Two Bedroom in South Tulsa
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

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

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

10/10 Excellent
"The room and everything in the hotel was spotless. The beds are always comfortable. The hot breakfast is always a pleasure. Staff was helpful and friendly."
David 3-night trip
Posted 2 hours ago
Hampton Inn & Suites Tulsa-Woodland Hills 71st-Memorial

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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 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?

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8: This vacation home rental outside of Winchester offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and 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 Okmulgee State Park and Tulsa Premium Outlets.

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.