Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Crescent Bar Condos Unit 143

8.6 out of 10, Excellent, (9)
"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. "
Crescent Bar Condos Unit 143

Steps from The Beach

2.0 star property
9.8 out of 10, Exceptional, (6)
"Clean and well maintained. "
Steps from The Beach

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

10.0 out of 10, Exceptional, (6)
"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."
The price is €527
includes taxes & fees
3 Sept - 4 Sept
Suite Home @ Cave B - 2BR - Walk to the Gorge

Quincy Home on Lavender Farm w/ River Views!

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

Crescent Bar Condo

10.0 out of 10, Exceptional, (12)
"Lovely unit, super clean, well maintained. Quick response from owner. Loved it!!!"
The price is €324
includes taxes & fees
28 Sept - 29 Sept
Crescent Bar Condo

Luxury @ Crescent Bar! Pool & Free Golf!

9.8 out of 10, Exceptional, (28)
"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!

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

10.0 out of 10, Exceptional, (17)
"ABSOLUTELY BREATHTAKING!! Highly recommend this property and host! We had an amazing time! They have literally thought of everything! Only a 10 min walk to the Gorge! We will definitely be back! Thank you! "
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

10.0 out of 10, Exceptional, (1)
"Very modern, clean, beautiful. Great throughout the entire space."
The price is €701
includes taxes & fees
28 Sept - 29 Sept
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

10.0 out of 10, Exceptional, (2)
"Great spot and great house"
The price is €439
includes taxes & fees
1 Sept - 2 Sept
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

10.0 out of 10, Exceptional, (22)
"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!"
PET-FRIENDLY, HOT TUB & SAUNA CaveB Lakeside Luxury Spa Retreat by The Gorge

2-bedroom townhome in enjoyable Crescent Bar with WiFi, AC, fitness room

2-bedroom townhome in enjoyable Crescent Bar with WiFi, AC, fitness room

Beautiful Sunserra home located on the 9th fairway of the golf course

10.0 out of 10, Exceptional, (8)
"Our stay was 100% as advertised and very comfortable! The house is beautifully appointed, great location, and Christy made the whole process very easy. Highly recommend! "
Beautiful Sunserra home located on the 9th fairway of the golf course

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

10.0 out of 10, Exceptional, (29)
"Amazing stay"
Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA

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

10.0 out of 10, Exceptional, (20)
"We thoroughly enjoyed our stay at Lakeside Oasis. Very quiet and away from the crowds. The frogs were entertaining as we soaked in the hot tub overlooking the lake. The house was very clean and well-stocked for cooking. It was the perfect getaway."
Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

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

10.0 out of 10, Exceptional, (86)
"Great resort area near the Gorge Amphetheatre"
Rent Like a Rock Star @ Hotel Rock in Sunserra, C-Bar!

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.

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

10.0 out of 10, Exceptional, (1)
"We had such a great stay! Our host, Amanda, was wonderful and communicated with us exceptionally from start to finish. The location was perfect—just a 10-minute walk to The Gorge. Everything was spotless and well-maintained, and the AC kept us cool during the summer heat. We’ll definitely be back and highly recommend this place to anyone!"
The price is €319
includes taxes & fees
3 Sept - 4 Sept
Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre

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

10.0 out of 10, Exceptional, (35)
"We really enjoyed our stay at this property! It was spotless and a great setup.The owner had amazing communication and perfectly clear instructions. Thank you!"
Crescent Bar Getaway-Pool/Beach/River, Gorge Concerts, Wineries, Sunshine & Ski!

Luxury View Home on the Columbia River, Golf, Wineries & Gorge Amphitheater

10.0 out of 10, Exceptional, (5)
"Loved this property! The owners were super helpful every step of the way. Great location, super clean, had all the amenities that were essential. Plus an added bonus, we were able to fit our cars and boat without the hassle of parking off site. Would highly recommend this property "
Luxury View Home on the Columbia River, Golf, Wineries & Gorge Amphitheater

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

9.4 out of 10, Exceptional, (16)
"Darcy was super responsive and the place was super clean. Perfect for an outdoors vacation and families, close to the Gorge Amphitheater"
The price is €568
includes taxes & fees
28 Sept - 29 Sept
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
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

Find out more about Winchester

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, apart-hotels, 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 favorite 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 depends 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 €319 per night. Entering your travel dates in the search wizard you might find 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 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?

Charming 3-bedroom house walking distance to the lake, restaurants, pet friendly: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 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.