Winchester Holiday Rentals from AU$165: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winchester has to offer?

Secluded River Cabin Getaway (Masten Cabin) : This holiday home rental outside of Winchester is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

Blue Mountain Cabin, secluded, perfect for couples, near main road

Front Royal

Wafaa L.

includes taxes & fees

16 June - 17 June

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Front Royal

Jake M.

includes taxes & fees

14 June - 15 June

The Pond Cabin

Linden

includes taxes & fees

15 June - 16 June

Newly renovated Farm cottage with Mountain views

Strasburg

Shannon H.

includes taxes & fees

14 June - 15 June

Hidden Gem on Hidden Valley Lane

Linden

Lisa W.

includes taxes & fees

14 June - 15 June

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Front Royal

Lisa H.

includes taxes & fees

14 June - 15 June

Apple Mountain House • Hot Tub • Game Room

Front Royal

Katia R.

includes taxes & fees

14 June - 15 June

NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline

Front Royal

"We stayed at this lovely cabin for a few days over the Thanksgiving holiday, and it was perfect. It was cozy, comfortable, and spotless…just the right size to feel at home. Natasha, the host, was wonderful. Even while traveling abroad, she communicated quickly and clearly, and we never had any issues reaching her.The kitchen was fully equipped for preparing meals, and every other room had everything we could possibly need. Thank you, Natasha - we’ll definitely be back!"

Indira A.

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Top Winchester Hotel Reviews

TRU By Hilton Winchester

10/10 Excellent

"Fabulous hotel"

The George Washington Hotel, A Wyndham Grand Hotel

8/10 Good

"The physical structure of this hotel would have put it at 5 stars, but it seems like they have a really nice property here, but don't know how to run it like a really nice hotel. First, the idea that a hotel of this caliber has an UNO pizza as their hotel is just strange. Also, the bar is gorgeous and well appointed, but it closes at 11 PM. Both nights we stayed there, the group wanted to stay longer and visit and buy drinks, but the first night we had to leave at 11 and the second night, following the wedding, there was nowhere to go. Lost opportunity there. Also, many guests we spoke to had problems with their room keys. urs didn't work on our second day there and a maid saw us trying to get it to work and just came over and swiped us in. My husband then went down and got new keys, but we were appreciative but also bothered that she let us in with no ID. Then the worst one was that the groom's parents' keys didn't work after the wedding. SO after 12AM they couldn't get into their room and there was nobody on duty. They had to call the National phone number for Wyndham to get someone to come and then, when someone named Phillip DID come, he was very rude to her. Fix your key problem. I liken the physical building and vibe with Hotel Bethlehem, William Penn, lovely historic hotels, but it sure isn't run with that kind of service."

Travelodge by Wyndham Winchester

2/10 Terrible

"The rooms were dirty. Breakfast was minimal. The coffee was instant pored into the coffee machine. Our drain in the tub was working so slow that taking a shower was filling the tub. When we reported it they said we will make note of it. Not, let us move you or send someone to fix it. We won’t stay here again."

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Enjoyed the pool and workout space very much. Everything was very tidy and felt like it was brand new. Typical hotel breakfast with waffles, eggs, bacon as well as the usual cold selection including hard boiled eggs. Excellent coffee in the lobby for our morning departure."

APM Inn & Suites

6/10 Okay

"We stayed at this hotel on the 10th of May, while heading to Tennessee. The room was clean & had everything that was needed, even treats. The staff were wonderful! So on the way back from Tennessee we booked there again, BUT….. the room wasn’t very nice & smelled bad (cigarettes, this is a no smoking hotel with fines posted in the rooms) I have severe asthma so I notified the staff & they really worked hard to get me another room but sadly, that room was worse then the room I was given. We had to leave & went to another hotel. They refunded my room… All in all they are kind people who are trying very hard, the problem is that they seem to be a hotel / transient living (some of the men looked “shady”) & that doesn’t seem to work well. They need to be one or the other….. I cannot recommend this place if you have any breathing issues. If you do book, please notify them before arriving about any concerns you may have. They really seem to care & will do their best to make you comfortable & happy!"

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$165 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.

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Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Secluded River Cabin Getaway (Masten Cabin): This holiday home rental outside of Winchester is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Winchester?

Choose from 12 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.

Winchester Holiday Rentals

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Check prices for these dates

Our top choices for Winchester holiday rentals

Blue Mountain Cabin, secluded, perfect for couples, near main road

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

The Pond Cabin

Newly renovated Farm cottage with Mountain views

Hidden Gem on Hidden Valley Lane

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Apple Mountain House • Hot Tub • Game Room

NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline

Cameron Charmer pristine downtown apt with double master suites

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Stargazing Dome + Hot Tub + Sauna + EV Charger, Luxury Cabin Near Harpers Ferry

Lunar Loft, with mountain views

Apple Mountain Retreat

Mountain home w/ hot tub & sunroom

Morocco Loft 2BR overlooking city walking mall

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

All-Inclusive 4BR • Mountain Views • Hot Tub

Mountain View Bungalow in Front Royal

Blue Mountain House - Hot Tub, Grill, Fire Table

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

TRU By Hilton Winchester

Find out more about Winchester

Explore a world of travel with Expedia

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