Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
9.8 out of 10, Exceptional, (68 reviews)
"The casita was very clean, cozy, and easy to access. The backyard pool was really fun, too!"
United States
Hayden
The price is €116
includes taxes & fees
20 Apr - 21 Apr
1 Bed Room Casita-Suite with Private Entrance

Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is €225
includes taxes & fees
21 Apr - 22 Apr
Hike, Sip & Explore: Couples Retreat in Fallbrook

Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
10.0 out of 10, Exceptional, (3 reviews)
"I happened to receive a complimentary upgrade during my visit, and it added a special touch to my stay. The cabin itself was wonderful and Cayla at Idyllwild Realty was great! The cabin was a perfect getaway and walking distance to town."
United States
Heather
The price is €120
includes taxes & fees
26 Apr - 27 Apr
Idyllwild Realty Vacations

Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
10.0 out of 10, Exceptional, (23 reviews)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is €237
includes taxes & fees
20 Apr - 21 Apr
Coral Tree House

The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe

The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe
Idyllwild-Pine Cove
9.8 out of 10, Exceptional, (25 reviews)
"Had a great time! "
United States
Jimmy S
The price is €312
includes taxes & fees
16 Apr - 17 Apr
The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (21 reviews)
"Very clean, I enjoyed the stay very quiet surroundings. "
United States
Sofia
The price is €241
includes taxes & fees
27 Apr - 28 Apr
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
Idyllwild-Pine Cove
8.8 out of 10, Excellent, (26 reviews)
"The place was great and so relaxing to stay in such a peaceful space."
United States
Rich C.
The price is €138
includes taxes & fees
20 Apr - 21 Apr
Secluded mystical cabin in Idyllwild-Pine Cove

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Everything was clean and the place was really close to town. "
United States
Jack B.
The price is €175
includes taxes & fees
23 Apr - 24 Apr
Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!

IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (41 reviews)
"just a quick one night stay- it was great"
United States
Rick M.
The price is €212
includes taxes & fees
27 Apr - 28 Apr
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!

Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo

Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (13 reviews)
"The property exceeded my expectations! Great location."
United States
Stephanie H.
The price is €197
includes taxes & fees
16 Apr - 17 Apr
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo

Romantic, private and surrounded by best Wineries!

Romantic, private and surrounded by best Wineries!
GlenOak Hills
10.0 out of 10, Exceptional, (23 reviews)
"Quiet, clean, cozy and a great location! Close to the wineries and casino. Would definitely recommend!"
United States
Yvonne M.
The price is €363
includes taxes & fees
23 Apr - 24 Apr
Romantic, private and surrounded by best Wineries!

Charming working ranch in the heart of Temecula wine country

Charming working ranch in the heart of Temecula wine country
Temecula
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and very accommodating. A home away from home."
United States
gulivardo
The price is €275
includes taxes & fees
21 Apr - 22 Apr
Charming working ranch in the heart of Temecula wine country

Cactus Garden Cottage…Best Location!!

Cactus Garden Cottage…Best Location!!
Fallbrook
10.0 out of 10, Exceptional, (63 reviews)
"Great location and had everything we needed for our short stay! "
United States
Tiffany V.
The price is €148
includes taxes & fees
27 Apr - 28 Apr
Cactus Garden Cottage…Best Location!!

Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown

Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (11 reviews)
"host was very kind and amazing! cabin is beautiful"
United States
Esmeralda O.
The price is €307
includes taxes & fees
28 Apr - 29 Apr
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown

"Rustic Elegance - A Woodland Escape"

"Rustic Elegance - A Woodland Escape"
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (24 reviews)
"Another Thanksgiving with family. We had a great stay… kitchen is fully stocked for a holiday meal, beds are comfortable and the wood burning stove is perfect! About a 30-40 min walk into Idyllwild but not a difficult one. Quiet neighborhood. Enjoyed the annual tree lighting. Only thing that would have made it that much better would’ve been some snow. Merry Christmas! "
United States
Nancy S.
The price is €477
includes taxes & fees
22 Apr - 23 Apr
"Rustic Elegance - A Woodland Escape"

The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.2 out of 10, Wonderful, (90 reviews)
"So good! Very nice place and friendly staff "
China
Zhicong
The price is €151
includes taxes & fees
19 Apr - 20 Apr
The Cottages at Golden Village Palms RV Resort

Ahwahnee-be Vintage Cabin - Three blocks to town!

Ahwahnee-be Vintage Cabin - Three blocks to town!
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (27 reviews)
"Fun town, beautiful setting, quiet."
United States
nancy d.
The price is €235
includes taxes & fees
21 Apr - 22 Apr
Ahwahnee-be Vintage Cabin - Three blocks to town!

Charming 1-bedroom apart with Sofa Bed in living room in Lake Elsinoire with AC

Charming 1-bedroom apart with Sofa Bed in living room in Lake Elsinoire with AC
Lake Elsinoire
8.0 out of 10, Very good, (3 reviews)
"The room was clean and everyone was very nice, beautiful house thank you so much! "
United States
jordan n.
The price is €146
includes taxes & fees
20 Apr - 21 Apr
Charming 1-bedroom apart with Sofa Bed in living room in Lake Elsinoire with AC

4-bedroom house in wonderful Perris with WiFi, AC

4-bedroom house in wonderful Perris with WiFi, AC
Perris
9.4 out of 10, Exceptional, (6 reviews)
"I love the house and host was very attentive "
United States
Jessica G.
The price is €363
includes taxes & fees
16 Apr - 17 Apr
4-bedroom house in wonderful Perris with WiFi, AC

Hobbit House - Heart of Town - Stunning Remodel

Hobbit House - Heart of Town - Stunning Remodel
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (25 reviews)
"Amazing cabin!"
United States
Chris R.
The price is €450
includes taxes & fees
20 Apr - 21 Apr
Hobbit House - Heart of Town - Stunning Remodel
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 €116 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?

Idyllwild Realty Vacations: This holiday home rental outside of Winchester comes with WiFi so that you can feel at home during your trip. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Winchester are 1 Bed Room Casita-Suite with Private Entrance and 5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!.

How many holiday rentals will I find in Winchester?

Choose from 36 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 Western Science Center, 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.