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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winchester vacation rentals

House (4 Bedrooms) | Interior

Family Home w/ Large Yard & Patio in Broken Arrow!

Family Home w/ Large Yard & Patio in Broken Arrow!
3.0 star property
Broken Arrow
$267 nightly
The price is $300
Jun 24 - Jun 25
Total with taxes and fees
Family Home w/ Large Yard & Patio in Broken Arrow!
Fridge, microwave, oven, stovetop

Safe, Sparkling Clean & Perfect for Families - Heart of Bixby

Safe, Sparkling Clean & Perfect for Families - Heart of Bixby
Bixby
9.8 out of 10, Exceptional, (18 reviews)
"It was very welcoming, had a grand home feel, and was every bit of clean. The perfect way to travel. "
United States
Jon J.
$276 nightly
The price is $298
Jun 27 - Jun 28
Total with taxes and fees
Safe, Sparkling Clean & Perfect for Families - Heart of Bixby
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.
$211 nightly
The price is $227
Jun 21 - Jun 22
Total with taxes and fees
Brand New Modern Getaway on Private Land!
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, (40 reviews)
"Perfect place to stay over night. Great central location and very comfortable."
United States
John L.
$168 nightly
The price is $181
Jun 21 - Jun 22
Total with taxes and fees
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa w/ Pool
Dining

Beautifully Remodeled 3-Bedroom Cozy Home!!

Beautifully Remodeled 3-Bedroom Cozy Home!!
Broken Arrow
9.6 out of 10, Exceptional, (54 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.
$245 nightly
The price is $263
Jun 21 - Jun 22
Total with taxes and fees
Beautifully Remodeled 3-Bedroom Cozy Home!!
Fridge, microwave, oven, stovetop

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.
$285 nightly
The price is $308
Jun 23 - Jun 24
Total with taxes and fees
1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
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, (16 reviews)
"Just as described"
United States
Melanie M.
$226 nightly
The price is $253
Jun 22 - Jun 23
Total with taxes and fees
Breezy Two Bedroom in South Tulsa
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.
$137 nightly
The price is $144
Jun 21 - Jun 22
Total with taxes and fees
1952 Royal Spartanette Trailer @ Teepee Drive-In
Fridge, microwave, oven, stovetop

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

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
South Tulsa
9.6 out of 10, Exceptional, (43 reviews)
"The kitchen was well equipped, and the beds were comfortable. The house was clean and we really enjoyed the fire place."
United States
Roy V.
$193 nightly
The price is $217
Jun 29 - Jun 30
Total with taxes and fees
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
Iron/ironing board, travel crib, free WiFi, 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 7 - Jul 8
Total with taxes and fees
The Red Door on 66th - 3BR/2BA Duplex
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.
$252 nightly
The price is $282
Jul 13 - Jul 14
Total with taxes and fees
We're All Mad Here! - A Wonderland Escape in Tulsa
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.
$262 nightly
The price is $282
Jun 21 - Jun 22
Total with taxes and fees
Newly Built Modern Getaway on Private Acreage!
Fridge, microwave, oven, stovetop

Scandi Home by Turnpike - KING Bed, Fast WiFi

Scandi Home by Turnpike - KING Bed, Fast WiFi
Broken Arrow
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay. It was clean, the house was equipped with everything we needed. Would certainly book again for future Oklahoma visits."
United States
Melissa B.
$297 nightly
The price is $319
Jun 28 - Jun 29
Total with taxes and fees
Scandi Home by Turnpike - KING Bed, Fast WiFi
Smart TV, fireplace

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, (10 reviews)
"Really neat place tucked away right along riverside parkway and Tulsa hills enjoyed are time here"
United States
brenen r.
$246 nightly
The price is $265
Jul 1 - Jul 2
Total with taxes and fees
Ivy's Charming 2 Bedroom 2 Bath with Jetted Tub
Outdoor pool

2 Bedroom 2 Bath Condo

2 Bedroom 2 Bath Condo
South Tulsa
10.0 out of 10, Exceptional, (3 reviews)
"Clean clean clean!Very welcoming and close to where I needed to be!"
United States
Rachael H.
$251 nightly
The price is $270
Jul 1 - Jul 2
Total with taxes and fees
2 Bedroom 2 Bath Condo
Property grounds

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
$296 nightly
The price is $313
Jun 22 - Jun 23
Total with taxes and fees
Modern Country Retreat w/ outdoor fire pit! Newly remodeled~Sleeps 9~board games
Exterior

Traveler's Delight! Southern Hills/ORU/RiverSpirit

Traveler's Delight! Southern Hills/ORU/RiverSpirit
South Tulsa
10.0 out of 10, Exceptional, (17 reviews)
"We could not have been more pleased with our stay at "Traveler's Delight!" The property was immaculate and the accommodations were lovely. The location was also central to the things we wanted to do and places we wanted to go while in Tulsa. We would definitely stay here again and highly recommend to anyone thinking of staying here! "
United States
Christie C.
$365 nightly
The price is $409
Jun 21 - Jun 22
Total with taxes and fees
Traveler's Delight! Southern Hills/ORU/RiverSpirit
Fridge, microwave, oven, stovetop

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.
$208 nightly
The price is $233
Jun 21 - Jun 22
Total with taxes and fees
Turkey Mountain Bungalow - Walk to the Trails
Interior

Downtown Okmulgee Aviator Apartment

Downtown Okmulgee Aviator Apartment
Okmulgee
10.0 out of 10, Exceptional, (1 review)
"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.
$268 nightly
The price is $292
Jun 21 - Jun 22
Total with taxes and fees
Downtown Okmulgee Aviator Apartment
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 1 - Jul 2
Total with taxes and fees
Groovy Getaway - Retro Vibes and Modern Comfort
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

Courtyard by Marriott Tulsa Woodland Hills

Courtyard by Marriott Tulsa Woodland Hills

10/10 Excellent
"Great location-right across the street from the mall and tons of food places like Clark Crew BBQ-one of the best places to eat EVER! Room was nice with a little sofa in there, however, the bed a more firm than usual. No complaints and would definitely book again without hesitation."
Amy 2-night trip
Posted 3 hours ago
Courtyard by Marriott Tulsa Woodland Hills

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 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.