Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Holiday Home in Winchester

9.8 out of 10, Exceptional, (58)
"Very nice property"
United States
Dillon T.
The price is €118
includes taxes & fees
1 Dec - 2 Dec
1 Bed Room Casita-Suite with Private Entrance

Villa in Temecula

10.0 out of 10, Exceptional, (51)
"Was everything we hoped for!"
United States
Brandon D.
Chateau Vino - French Style Chalet

Cabin in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (4)
"We loved our stay here! The lighthouse theme was so cute and the house was decorated impeccably. It was also very clean and outfitted with towels, amenities, coffee, etc. so we had everything we needed!Great communication with the property owner as well! Would recommend!"
United States
Christina S.
The price is €250
includes taxes & fees
1 Dec - 2 Dec
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Aparthotel in Moreno Valley

3.0 star property
9.8 out of 10, Exceptional, (23)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is €118
includes taxes & fees
1 Dec - 2 Dec
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Cabin in Idyllwild-Pine Cove

9.0 out of 10, Wonderful, (12)
"Nice rustic cabin close to town but secluded. "
United States
Jacob H.
The price is €140
includes taxes & fees
2 Dec - 3 Dec
Secluded mystical cabin in Idyllwild-Pine Cove

Cottage in Hemet

3.0 star property
9.4 out of 10, Exceptional, (78)
"Amazing stay, will visit again"
United States
Miguel
The price is €153
includes taxes & fees
1 Dec - 2 Dec
The Cottages at Golden Village Palms RV Resort

Villa in GlenOak Hills

8.4 out of 10, Very good, (7)
The price is €964
includes taxes & fees
3 Dec - 4 Dec
Amazing Views Villa with Spa / Close to Winery

Holiday Home in Cross Creek

9.6 out of 10, Exceptional, (34)
"Wonderful stay. Enjoyed accommodations and area."
United States
Ken K.
Exclusive Resort Style Estate in Temecula

Apartment in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (49)
"Great location and amenities. Great communication with host. "
United States
Harrison H.
Family friendly, Full Kitchen, EV Charger Level 2, A/C, Easy Parking, Fireplace

Holiday Home in Lake Elsinore

2.0 star property
The price is €127
includes taxes & fees
9 Dec - 10 Dec
Lakeside Escape, Cozy Getaway

Villa in Temecula

9.0 out of 10, Wonderful, (25)
"The house was perfect. The pool area needed a little work - lacking a few umbrellas. The extra fridge did not work - but all in all it was nice house and pool. Loved the extra room with the pool table/bar and ping pong. Nice and quiet area of Temecula."
United States
Susan S.
Beautiful Villa located in Temecula Wine Country

Cottage in Fern Valley

3.0 star property
6.8 out of 10, (11)
"Great property, well kept, great for extended vacations"
United States
Domonick
The price is €431
includes taxes & fees
1 Dec - 2 Dec
Always Inn Idyllwild Vacation Cottages

Cabin in Fallbrook

3.0 star property
10.0 out of 10, Exceptional, (22)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is €205
includes taxes & fees
7 Dec - 8 Dec
Coral Tree House

Cabin in Idyllwild

9.8 out of 10, Exceptional, (315)
"The cabin was perfect I had my daughters 1st birthday here and we dressed as fairy’s and in forest theme outfits the wifi was perfect and there was activities for all of my family to enjoy"
United States
Ayalkawut
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

Holiday Home in Temecula

10.0 out of 10, Exceptional, (4)
"Nice setup with almost an acre of property. 5 minutes from Galway Downs and nice elevated views of the valley. "
United States
Jill W.
Woodchuck Retreat & RV Park

Villa in Valle De Los Caballos

10.0 out of 10, Exceptional, (26)
"The house and property were amazing! Highly recommend. "
United States
Michael E.
Temecula Wine Country Villa / Save up to 30% Long Stay

Holiday Home in Idyllwild

2.0 star property
9.6 out of 10, Exceptional, (15)
"Everything was amazing , super spacious close to town "
United States
Marie
3-Bedrooms in Idyllwild - AC, Jacuzzi, Sauna, Fitness-Game Room, Epic Views

Holiday Home in Valle De Los Caballos

9.6 out of 10, Exceptional, (192)
"Our stay was AWESOME! Our large family was able to be accommodated. We enjoyed playing pickle ball on the tennis courts. The cool nights were warmed by the spa. The hot days we cooled off in the pool, and we walked the gorgeous lit up grounds at night. Thank you for a wonderful time."
United States
Donna C.
Paradise Vacation Estate - Largest Luxury Private Vacation Resort

Holiday Home in Valle De Los Caballos

9.8 out of 10, Exceptional, (42)
"We thoroughly enjoyed the property and its grounds. All was in good shape and properly maintained."
United States
Gerald S.
7 BR/5.5 bath PERMITTED TEMECULA WINE COUNTRY VACATION RENTAL

Villa in Valle De Los Caballos

9.2 out of 10, Wonderful, (39)
"The property is so nice and very relaxing. "
United States
Lilibeth S.
The price is €976
includes taxes & fees
2 Dec - 3 Dec
Villa with indoor pool in Temecula wine country-VRBO
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

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 €118 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?

Exclusive Resort Style Estate in Temecula: This holiday home rental outside of Winchester is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 32 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. K1 Circuit and Pechanga Resort & Casino 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.