Winchester Vacation Rentals from ￥22,557: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winchester?

Suite Home @ Cave B - 2BR - Walk to the Gorge : 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. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Vacation Rentals in Winchester

"Lovely unit, super clean, well maintained. Quick response from owner. Loved it!!!"

￥53,753 total

includes taxes & fees

Jul 16 - Jul 17

"Darcy was super responsive and the place was super clean. Perfect for an outdoors vacation and families, close to the Gorge Amphitheater"

￥71,813 total

includes taxes & fees

Jul 16 - Jul 17

"Host was very responsive and took care of any questions or concerns we had. Check in and out was very smooth and directions were very clear. "

"We appreciated the close proximity to the Gorge! Very clean rental with beautiful view. "

"We stayed here over the weekend and the place is in a very convienent location. Alan is a great host. We would recommend staying here again."

￥74,868 total

includes taxes & fees

Jul 15 - Jul 16

"Really cool place to stay. Pretty. Close to the venue. Will stay there again."

"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. "

"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!! "

"We came for a quick weekend away and it was perfect! "

￥82,792 total

includes taxes & fees

Jul 15 - Jul 16

"Great spot and great house"

￥64,871 total

includes taxes & fees

Jul 15 - Jul 16

"My fiends and my wife had a great a stay at the cabin; loved all the amenities in the cabin, and Karyn is such a great host!"

"We absolutely loved our stay here! The property was immaculate, comfortable, and beautifully decorated, making us feel right at home from the moment we arrived. The location is perfect—conveniently close to Soap Lake and local attractions. Michelle is an incredibly welcoming and attentive host providing thoughtful touches that added to our comfort. Pet-friendly accommodations were definitely appreciated as our furry friend enjoyed the stay as much as we did. Highly recommend this VRBO for anyone...

Smart TV, fireplace, books, computer monitors

"Amazing stay"

"Perfect house for a family reunion weekend!"

"Clean and well maintained. "

￥49,475 total

includes taxes & fees

Jul 22 - Jul 23

"Would definitely stay again. "

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Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Recent reviews of Winchester properties

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

5/5 Excellent

Perfect getaway for the gorge!

"We stayed at this property during a 3-day festival weekend and it was absolutely perfect. We loved having the back deck with the couch, fire pit and hot tub to relax on in the morning and evenings. The beds were comfortable including the living room pullouts and we had enough space to feel relaxed, even with the beds in the shared spaces. It was only a quick walk (maybe 15 minutes) to the gorge entrance so it was very easy to go back and forth. The kitchen was fully stocked and we were able to cook our own meals during the weekend instead of spending a lot of money at the show. We loved it and would absolutely stay here again! Highly recommend "

A verified traveler from Fort Worth stayed at Breathtaking Gorge Ampitheater, Cave B Winery and SageCliffe Resort view home

Posted 5 days ago

Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

5/5 Excellent

Fully stocked unit!!

"We have stayed at these condos for the past few years and this is by far, the best unit we have stayed in! It was fully stocked with all the little things, appliances, and condiments/spice. We had an awesome time and the property was top notch! "

A verified traveler from Bellingham, WA stayed at Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

Posted 8 days ago

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

5/5 Excellent

"Everything was wonderful! House is amazing, pool was enjoyable for the entire family. My only feedback is that the lady who lives to the left is a busy body. She's nice enough, just has to be in your business. We just ignored her and enjoyed our weekend and things were great. "

A verified traveler stayed at Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA

Posted 13 days ago

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

5/5 Excellent

Beautiful location for a special celebration

"We are local to the area and were looking for a place for the bride and bridesmaids to get ready for a wedding. It was a perfect spot for the 5 girls to stay and get ready. Us moms of the bride and groom came in the morning to get ready with the girls, it was perfect. Then the newly wed couple were able to go back out and spend a couple nights in the place to relax after their wedding. It was a great place to stay close to home but with the feel of someplace special and great get away. The owner was great to work with and had prompt responses when we wanted to add an extra night to the stay. Thank you for helping to make the special weekend so much fun. "

A verified traveler stayed at Suite Home @ Cave B - 2BR - Walk to the Gorge

Posted 1 month ago

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals near popular local attractions in Winchester, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Winchester?

Suite Home @ Cave B - 2BR - Walk to the Gorge: 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. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Park. Soap Lake and Moses Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Winchester. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.

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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Crescent Bar Condo

Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

Crescent Bar Condos Unit 143

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

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

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

Luxury @ Crescent Bar! Pool & Free Golf!

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

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

2-bedroom condo at Cave B Winery with WiFi, AC~Adjacent to Gorge Ampitheatre

3-bedroom house in charming Moses Lake with AC, fitness room, WiFi

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

Quincy Home on Lavender Farm w/ River Views!

Charming 3-bedroom house walking distance to the lake, restaurants, pet friendly

Crescent Bar Condo: On the river with Pool, Gorge shuttle/Wineries, AC

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

Picturesque Moses Lake House w/ Boating Dock

Steps from The Beach

Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre

Condo in Crescent Bar Resort—20 minutes from the Gorge amphitheater.

Find out more about Winchester

Recent reviews of Winchester properties

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

Masters Inn

Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

Soap Lake Natural Spa & Resort

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

Best Western Rama Inn

Quincy INN and Suites

Holiday Inn Express & Suites George Quincy South by IHG

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

Frequently asked questions