Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winchester

Breathtaking Gorge Ampitheater, Cave B Winery and SageCliffe Resort view home
10.0 out of 10, Exceptional, (17)
"Will come again!"
United States
Gabe B.
Breathtaking Gorge Ampitheater, Cave B Winery and SageCliffe Resort view home
Steps from The Beach
2.0 star property
9.8 out of 10, Exceptional, (7)
"Clean and well maintained. "
United States
Lisa M.
Steps from The Beach
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
9.4 out of 10, Exceptional, (19)
"Home was well stocked and clean, they had great communication and checked in during check in and our stay. Overall a great place and would rent again! "
United States
Jennifer B.
The price is AU$721
includes taxes & fees
25 Oct - 26 Oct
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
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."
Canada
Jennette M.
The price is AU$768
includes taxes & fees
25 Oct - 26 Oct
Suite Home @ Cave B - 2BR - Walk to the Gorge
Crescent Bar Condo
10.0 out of 10, Exceptional, (17)
"Great place to stay in Cresent bar. The condo was clean and very nice. Complex is great with the pool in the middle. "
United States
Sigurros
The price is AU$566
includes taxes & fees
26 Oct - 27 Oct
Crescent Bar Condo
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."
United States
Melanie C.
The price is AU$956
includes taxes & fees
18 Nov - 19 Nov
2-bedroom condo at Cave B Winery with WiFi, AC~Adjacent to Gorge Ampitheatre
Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre
10.0 out of 10, Exceptional, (2)
"Always a great getaway "
United States
Ryan D.
The price is AU$661
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre
Quincy Home on Lavender Farm w/ River Views!
3.0 star property
Quincy Home on Lavender Farm w/ River Views!
PET-FRIENDLY, HOT TUB & SAUNA CaveB Lakeside Luxury Spa Retreat by The Gorge
10.0 out of 10, Exceptional, (23)
"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!"
United States
Tianchu L.
PET-FRIENDLY, HOT TUB & SAUNA CaveB Lakeside Luxury Spa Retreat by The Gorge
Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat
10.0 out of 10, Exceptional, (21)
"Wonderful yurt! Great folks running the show! The property needs a dishwashing station is all."
United States
Elliott
Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat
3-bedroom house in charming Moses Lake with AC, fitness room, WiFi
10.0 out of 10, Exceptional, (2)
"Great spot and great house"
United States
Mitch H.
3-bedroom house in charming Moses Lake with AC, fitness room, WiFi
Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA
10.0 out of 10, Exceptional, (30)
"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. "
United States
Lacey S.
Lakeview Golf Course - Private Pool/Hot Tub - Pet Friendly - Soap Lake, WA
Crescent Bar Unit 102
9.6 out of 10, Exceptional, (5)
"We had a wonderful time staying at Crescent Bar. We spent most of our time poolside. The pool and grounds were very well maintained. Check-in and check-out were very easy and communication with property manager was great. We will certainly consider staying in this unit again for next year's trip!"
United States
Mary D.
Crescent Bar Unit 102
Waterfront, Stunning Views, Private Beach, and Close To Concerts
9.8 out of 10, Exceptional, (14)
"We had such a great stay! The location is awesome - beautiful view and a path down to the water from the back patio. The host provides water toys and beach towels, the floating mat is so fun! The house is also pretty close to Tower Pizza, where you can find great food and new friends. Communication was easy and informative. Thanks for a great weekend! "
United States
Maddy L.
Waterfront, Stunning Views, Private Beach, and Close To Concerts
Moses Lake Golf Retreat @Moses Pointe Golf Course Hot Tub Sauna Pizza Oven
9.6 out of 10, Exceptional, (5)
"Great location and great space for our needs. Didn’t realize that the 3rd bedroom was a sofa bed. And there wasn’t any bedding left out. Tried to message the host ahead of time but never heard back. Also I didn’t have check out inst"
United States
Teresa G.
The price is AU$1,037
includes taxes & fees
26 Oct - 27 Oct
Moses Lake Golf Retreat @Moses Pointe Golf Course Hot Tub Sauna Pizza Oven
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...
United States
Jaclyn M.
2 Bedroom Downtown Condo above Gym with Pool Hot tubs sauna etc.
Beautifully Updated Crescent Bar Condo FREE GOLF
10.0 out of 10, Exceptional, (13)
"Great place to stay - exactly as described! Beds are comfortable, very clean, and the kitchen is well stocked. Will stay again when we return to Sunserra!"
United States
Kris M.
Beautifully Updated Crescent Bar Condo FREE GOLF
Crescent Bar Getaway-Pool/Beach/River, Gorge Concerts, Wineries, Sunshine & Ski!
10.0 out of 10, Exceptional, (36)
"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!"
United States
Jesse C.
Crescent Bar Getaway-Pool/Beach/River, Gorge Concerts, Wineries, Sunshine & Ski!
Luxe Winery Spa Retreat with Columbia Gorge & Lake Views 2bd/2ba
10.0 out of 10, Exceptional, (1)
"Beautiful place and very clean"
United States
Ashley R.
Luxe Winery Spa Retreat with Columbia Gorge & Lake Views 2bd/2ba
Crescent Bar Condos Unit 143
8.4 out of 10, Very good, (12)
"We had a very nice stay. The condo was clean and well stocked. Great communication and easy check in/check out. "
United States
Rachel Y.
Crescent Bar Condos Unit 143
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

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, 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 favourite 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 depend 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 AU$566 per night. Entering your travel dates in the search wizard might find you 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?

Steps from The Beach: This holiday home rental outside of Winchester is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.