Winchester Holiday Rentals

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Holiday Rentals in Winchester

Crescent Bar Condos Unit 143

8.4 out of 10, Very good, (5)
"Nice clean accurate listing."
Crescent Bar Condos Unit 143

Breathtaking Gorge Ampitheater, Cave B Winery and SageCliffe Resort view home

10.0 out of 10, Exceptional, (12)
"Great place, we’ll be back! "
Breathtaking Gorge Ampitheater, Cave B Winery and SageCliffe Resort view home

Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

10.0 out of 10, Exceptional, (18)
"This property is amazing. The decor is really chic and well done. The space is clean and modern. Plenty of space with two large bathrooms. It was the perfect home base for a weekend of concerts at the gorge right next door. We would absolutely stay again. Super easy communication with host, 5 stars for sure. Wish we could have stayed longer"
Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

Cave Beaux at the Gorge - walk to concerts w/hot tub

10.0 out of 10, Exceptional, (12)
"Great house! Easy to access. Would definitely stay there for another concert. "
Cave Beaux at the Gorge - walk to concerts w/hot tub

Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA

10.0 out of 10, Exceptional, (25)
"Another great stay. The kids lived in the pool, the hot tub was great for the adults. The remodel looks great. "
Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA

Quincy Home on Lavender Farm w/ River Views!

10.0 out of 10, Exceptional, (21)
"Our group really enjoyed our stay. Between the amazing views, proximity to the Gorge, and comfort of the home I wish we could have stayed longer! 10/10 would stay again!"
Quincy Home on Lavender Farm w/ River Views!

Crescent Bar Unit 102

10.0 out of 10, Exceptional, (3)
"We had a great time at your place. We had everything we need and it was as expected."
Crescent Bar Unit 102

Rent Like a Rock Star @ Hotel Rock in Sunserra, C-Bar!

10.0 out of 10, Exceptional, (81)
"Our stay at Hotel Rock was absolutely amazing. Super nice, very clean, stunning views, and David is a great host! We will definitely stay at Hotel Rock in the future!!! If anyone is planning on going to an event at The Gorge, check with David for ticket availability before buying online. Pretty easy to book this very nice place to stay and buy great seats from David!!!"
Rent Like a Rock Star @ Hotel Rock in Sunserra, C-Bar!

*PET FRIENDLY* HOT TUB & SAUNA CaveB Lakeside Luxury Spa Retreat by The Gorge

9.8 out of 10, Exceptional, (20)
"We had an awesome time in this stay. Loved the decor, the openness and the awesome hosts. Thanks!!"
*PET FRIENDLY* HOT TUB & SAUNA CaveB Lakeside Luxury Spa Retreat by The Gorge

Moses Lake Golf Retreat @ Resorts At Moses Point Links Golf Course

9.4 out of 10, Exceptional, (3)
"Property was absolutely perfect "
The price is AU$909
includes taxes & fees
23 Nov - 24 Nov
Moses Lake Golf Retreat @ Resorts At Moses Point Links Golf Course

Well Appointed Oasis in the Sun! ☀️⚓️🏖 Pool, Beach, Boat Launch, Gorge, Wineries

10.0 out of 10, Exceptional, (25)
"Our stay was wonderful. The condo and the grounds were perfect."
Well Appointed Oasis in the Sun! ☀️⚓️🏖 Pool, Beach, Boat Launch, Gorge, Wineries

Waterfront, Stunning Views, Private Beach, and Close To Concerts

9.8 out of 10, Exceptional, (13)
"The property had a gorgeous view of the river. Perfect for a concert weekend. It was nice to have a full kitchen and and dronk coffee on the back patio. We liked the bonus of access to water toys although we prefered the beach at Riverbend Park."
Waterfront, Stunning Views, Private Beach, and Close To Concerts

Newly Renovated! CB Condo unit 104 (sleeps up to 8)

8.8 out of 10, Excellent, (12)
"Despite unforeseen weather obstacles our host was very helpful and responsive. Great family property. You really can’t beat the location and the pool. I would definitely come back. Thanks for a great vacation."
Newly Renovated! CB Condo unit 104 (sleeps up to 8)

Quincy Home on Lavender Farm w/ River Views!

3.0 star property
Quincy Home on Lavender Farm w/ River Views!

Suite Home @ Cave B - 2BR - Walk to the Gorge

10.0 out of 10, Exceptional, (3)
"Beautiful house, had everything we needed. We cooked and enjoyed the patio and views. Close walk to the Gorge for concerts and the winery."
The price is AU$924
includes taxes & fees
3 Dec - 4 Dec
Suite Home @ Cave B - 2BR - Walk to the Gorge

Lovely Crescent Bar Condo w/ Community Amenities!

9.8 out of 10, Exceptional, (6)
"We had a great time! We stayed there because it was fairly close to the Gorge. The pool was nice. We enjoyed our stay there!"
Lovely Crescent Bar Condo w/ Community Amenities!

Crescent Bar Getaway-Pool/Beach/River, Gorge Concerts, Wineries, Sunshine & Ski!

10.0 out of 10, Exceptional, (34)
"We loved our stay and Erica was extremely quick to respond to my messages and was super forgiving when I told her we accidentally drove off with a parking pass…oops!!! lol we will definitely stay here again!! "
Crescent Bar Getaway-Pool/Beach/River, Gorge Concerts, Wineries, Sunshine & Ski!

Luxury @ Crescent Bar! Pool & Free Golf!

9.8 out of 10, Exceptional, (22)
"We had a great time here, the property was very clean, there were plenty of towels (and ketchup ;) ) and the beds were some of the best we have had in a VRBO. "
Luxury @ Crescent Bar! Pool & Free Golf!

2 Bedroom Downtown Condo above Gym with Pool Hot tubs sauna etc.

8.6 out of 10, Excellent, (4)
"We were placed in a different unit than we had reserved which reduced the number of beds so one of my sons had to sleep on the couch. The host responded to our communications but what he had to say was disappointing and unhelpful including telling me they don’t provide hand towels or washcloths in any of their units but there were paper towels in the kitchen. One of the beds had a flat sheet draped on it but it wasn’t tucked and there was no blanket for that room. Is a made bed and hand towel...
2 Bedroom Downtown Condo above Gym with Pool Hot tubs sauna etc.

Studio Condo above downtown Gym- close to Gorge

10.0 out of 10, Exceptional, (6)
"Convenient, safe, clean fun location with pool and gym access in historic building."
Studio Condo above downtown Gym- close to Gorge
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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Other types of properties in Winchester you may be interested in

Microtel Inn & Suites by Wyndham George

3.0 star property
9.0 out of 10, Wonderful, (362)
"Convenient off the freeway. Room very clean. Quiet. Would recommend."
The price is AU$172
includes taxes & fees
24 Nov - 25 Nov
Microtel Inn & Suites by Wyndham George

Best Western Rama Inn

2.5 star property
8.8 out of 10, Excellent, (633)
"The pool was super cold but that didn't stop the kids from going in!"
The price is AU$186
includes taxes & fees
23 Dec - 24 Dec
Best Western Rama Inn

Sagecliffe Resort & Spa

4.5 star property
8.6 out of 10, Excellent, (54)
"It is a great place to come and relax, yet close to home. The restaurant offers a farm-to-table menu, a good selection of wine or drinks, and fabulous views of the Gorge. "
The price is AU$345
includes taxes & fees
8 Dec - 9 Dec
Sagecliffe Resort & Spa
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental 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?

Cave Beaux at the Gorge - walk to concerts w/hot tub: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Quincy Aquatic Center, or get outside and enjoy nature at Soap Lake. Masquers Theater of Soap Lake and Moses Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.