Winchester Vacation Rentals from $121: Search Short-Term Rentals

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

Secluded River Cabin Getaway (Masten Cabin) : This vacation home rental near Winchester is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 vacation rentals

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

Front Royal

Wafaa L.

$210 nightly

Jun 14 - Jun 15

Total with taxes and fees

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

Front Royal

Jake M.

$202 nightly

Jun 14 - Jun 15

Total with taxes and fees

The Pond Cabin

Linden

$414 nightly

Jun 14 - Jun 15

Total with taxes and fees

Newly renovated Farm cottage with Mountain views

Strasburg

Shannon H.

$275 nightly

Jun 14 - Jun 15

Total with taxes and fees

Hidden Gem on Hidden Valley Lane

Linden

Lisa W.

$411 nightly

Jun 14 - Jun 15

Total with taxes and fees

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Front Royal

Lisa H.

$392 nightly

Jun 14 - Jun 15

Total with taxes and fees

Apple Mountain House • Hot Tub • Game Room

Front Royal

Katia R.

$479 nightly

Jun 14 - Jun 15

Total with taxes and fees

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.

$407 nightly

Jun 16 - Jun 17

Total with taxes and fees

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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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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 vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

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

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

How many vacation rentals will I find in Winchester?

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

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of 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 vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.

Winchester Vacation Rentals

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Check prices for these dates

Our top choices for Winchester vacation 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 vacation 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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