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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (50)
"Perfect for a quick overnight stay. "
The price is €118
includes taxes & fees
27 Aug - 28 Aug
1 Bed Room Casita-Suite with Private Entrance

6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides

6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (48)
"Really amazing stay! The hosts were so responsive and made sure that me and my friends were comfortable throughout our stay. The house was even better than the photos and it was so nice!! "
Chateau Vino - French Style Chalet

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.2 out of 10, Wonderful, (72)
"This is a hidden jem in Hemet love the pools the grounds are well maintained and I will definitely be staying here again"
The price is €152
includes taxes & fees
27 Aug - 28 Aug
The Cottages at Golden Village Palms RV Resort

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

9.6 out of 10, Exceptional, (187)
"Such a fun house to celebrate my wedding weekend in with family. Highly recommend."
Paradise Vacation Estate - Largest Luxury Private Vacation Resort

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

3.0 star property
9.8 out of 10, Exceptional, (21)
"Our stay was pleasant, office manger kind and helpful with "
The price is €117
includes taxes & fees
29 Aug - 30 Aug
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Adults 21+, Bring your peace or your party - more seclusion with less intrusion

4.0 out of 10, (1)
"when we checked in, we had a few sites to choose from and but none of them seemed to fit our 10person tent, so we had "
The price is €38
includes taxes & fees
18 Sept - 19 Sept
Adults 21+, Bring your peace or your party - more seclusion with less intrusion

5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

9.8 out of 10, Exceptional, (306)
"Our family loved the Strawberry Corner property for many reasons. The house gave each one of us the perfect place to relax and renew. We took turns in the hammock, swinging our worries away while gazing at the tall tree tops. The host's attention to details and decor made each room a delight. My daughter loved the Cowboy-themed bathroom with the big tub. My teenage son loved having his own "Cowboy Cabin", with TV and bathroom out by the game room. My mom and I loved working side by side in the...
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

Cactus Garden Cottage…Best Location!!

10.0 out of 10, Exceptional, (47)
"Perfect little place and I was able to get Uber, so that was great!"
The price is €150
includes taxes & fees
27 Aug - 28 Aug
Cactus Garden Cottage…Best Location!!

Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

2.0 star property
9.4 out of 10, Exceptional, (43)
"Loved the lakeside mansion for our Muslim women's retreat! It was private and spacious and clean! Only thing was, the fan remote had been lost so it was cold in the living room and some of the beds made some noise but other than that, great experience!"
Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

Wine Country Cottage W/Amazing Pano-Great Reviews!

9.4 out of 10, Exceptional, (26)
"This listing is exactly as presented. Cute, comfortable and convenient for my needs! Just loved my time there! Be sure to watch for the hot air balloons that regularly float overhead - very cool!"
Wine Country Cottage W/Amazing Pano-Great Reviews!

Wine Country Reserves

9.6 out of 10, Exceptional, (21)
"Wonderful place to stay! Extremely clean and well maintained. Nicely designed with all amenities we could think of for relaxing! I highly recommend you book it!"
Wine Country Reserves

Coral Tree House

3.0 star property
10.0 out of 10, Exceptional, (19)
"Michelle and Greg were great host they very kind and generous. Very knowledgeable about the surrounding area. Absolutely lovely place to stay."
Coral Tree House

Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

9.8 out of 10, Exceptional, (104)
"This VRBO was truly amazing. We had a large group & Vlada’s place was perfect. No one felt crowded, plenty of amenities & the kitchen was perfect for preparing large meals. Vlada was very friendly & she made herself available with quick response to any questions or concerns. "
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub

2.0 star property
9.6 out of 10, Exceptional, (11)
"We had a great time at this vrbo! Close to restaurants, coffee shops and other shops.The pool and tub was amazing and there was plenty of space for our 12 person group.The only real downside was the coffee machine wasn't working when we were there and had issues using the outlets on that wall in the kitchen. "
The price is €299
includes taxes & fees
14 Sept - 15 Sept
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub

Welcome to Love at First Syrah! Single Story home w/pool/spa/ 7 bedrooms & more!

9.4 out of 10, Exceptional, (6)
Welcome to Love at First Syrah! Single Story home w/pool/spa/ 7 bedrooms & more!

The Most Popular Vacation Rental in Wine Country!

10.0 out of 10, Exceptional, (130)
"The location of this house was perfect being central to most wineries (also walking distance to a few). We loved the common spaces, especially the open kitchen / living space. Definitely recommend for a large group, as the # of bedrooms and bathrooms were perfect!"
The Most Popular Vacation Rental in Wine Country!

Wine Country Estate with Vineyard Views, Pool, Spa, Fire-pit, all bedrms w/bath

9.8 out of 10, Exceptional, (96)
"Great location, beautiful house with amazing views!"
Wine Country Estate with Vineyard Views, Pool, Spa, Fire-pit, all bedrms w/bath

House with pool/spa/minutes to wineries

8.8 out of 10, Excellent, (33)
"The property served our staff members who were in town for work. While the property was about 20-30 minutes away from our work locations we found that the property was worth the drive. The morning views from the porch were amazing and even made my coffee taste a little better. The host was very responsive and accommodated our sometimes strange working hours. Thank you for making our stay amazing. "
The price is €977
includes taxes & fees
1 Sept - 2 Sept
House with pool/spa/minutes to wineries

Close to all wineries, paved roads, pool, spa, views! Easy to get around!!

9.4 out of 10, Exceptional, (77)
"Great space for everyone. Cooked on grill and had a nice dinner. Close to all wineries. "
Close to all wineries, paved roads, pool, spa, views! Easy to get around!!
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 €38 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

Are there holiday rentals 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. Winchester is known for its wineries and coffee shops. Make sure you have time to check out the bars while you're in the area.

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

1 Bed Room Casita-Suite with Private Entrance: This highly rated holiday home rental in Winchester offers an outdoor pool, a pool table and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Winchester?

Choose from 31 Expedia holiday rentals in Winchester for a memorable holiday.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Orange Empire Railroad Museum, or get out into nature at a spot like Diamond Valley Lake Marina. Pechanga Resort & Casino and Menifee Lakes Golf Course 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 like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.