Lodging Image

Search Holiday Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester holiday rentals

1. 1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
9.8 out of 10, Exceptional, (98 reviews)
"the room was very cozy!! the host amazing. I would definitely stay again"
United States
Isabel
The price is £82
includes taxes & fees
17 Nov - 18 Nov
1 Bed Room Casita-Suite with Private Entrance

2. Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga

Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
Winchester
10.0 out of 10, Exceptional, (11 reviews)
"The room was exactly what we needed while traveling through with our family for a tournament in Temecula. Plenty of room and everything we needed!"
United States
Vanna S.
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga

3. 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, (113 reviews)
"Staff was very friendly , very clean , beautiful place"
United States
Albert
The price is £134
includes taxes & fees
16 Nov - 17 Nov
The Cottages at Golden Village Palms RV Resort

4. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
10.0 out of 10, Exceptional, (24 reviews)
"Two bedrooms and two bathrooms was really nice! We stayed in the Kid Gallahad room. The kitchen was well stocked. It was relaxing. We will stay there again."
United States
William
The price is £106
includes taxes & fees
6 Dec - 7 Dec
Idyllwild Realty Vacations

5. The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!

The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
Valle De Los Caballos
9.6 out of 10, Exceptional, (19 reviews)
"Very nice house! Everything was very comfortable and wonderful location"
United States
Tina S.
The price is £171
includes taxes & fees
17 Nov - 18 Nov
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!

6. Western Horizon Home

Western Horizon Home
Hemet
8.8 out of 10, Excellent, (24 reviews)
"Great place to stay. Great host. Quiet neighborhood. Close to shopping centers."
United States
Taman D.
The price is £290
includes taxes & fees
15 Nov - 16 Nov
Western Horizon Home

7. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (53 reviews)
"Quiet room, comfortable bed. Loved the easy parking and calm vibe late at night."
United States
Anonymous traveller
The price is £62
includes taxes & fees
18 Nov - 19 Nov
1 King Bed | Non-Smoking, Micfridge

8. Romantic, private and surrounded by best Wineries!

Romantic, private and surrounded by best Wineries!
GlenOak Hills
10.0 out of 10, Exceptional, (31 reviews)
"We loved our stay! Home was clean, comfortable, and the decor was amazing!"
United States
Dana O.
The price is £287
includes taxes & fees
15 Nov - 16 Nov
Romantic, private and surrounded by best Wineries!

9. Tranquil Studio at Eagle Creek

Tranquil Studio at Eagle Creek
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (1 review)
"We had a fabulous time in Idyllwild! The small-town vibe, the kindness of the locals, and the spectacular hikes did not disappoint. Our host, Heather, went above and beyond by upgrading us to a larger property because she thought the cabin we originally booked would be too tight for four people. We truly felt like VIPs in the main house. Everything was top-notch, beautifully kept, and felt incredibly homey. Check-in and check-out were completely seamless thanks to the keypad system. This was...
United States
Delphine
The price is £174
includes taxes & fees
16 Nov - 17 Nov
Tranquil Studio at Eagle Creek

10. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
10.0 out of 10, Exceptional, (3 reviews)
"This is a decent spot with dependable WiFi and parking close by."
United States
Anonymous traveller
The price is £66
includes taxes & fees
16 Nov - 17 Nov
1 King Bed | Non-Smoking

11. Romantic Villa • Pool • Surrounded by Wineries

Romantic Villa • Pool • Surrounded by Wineries
Valle De Los Caballos
10.0 out of 10, Exceptional, (11 reviews)
"Great pool, pretty property"
United States
kelly s.
The price is £394
includes taxes & fees
17 Nov - 18 Nov
Romantic Villa • Pool • Surrounded by Wineries

12. Rejuvenate! Remodeled home, 180-view on 4-acres.

Rejuvenate! Remodeled home, 180-view on 4-acres.
Valle De Los Caballos
10.0 out of 10, Exceptional, (26 reviews)
"Owner and property manager were responsive; home was nice and we enjoyed the stay"
United States
Scot L.
The price is £304
includes taxes & fees
7 Dec - 8 Dec
Rejuvenate! Remodeled home, 180-view on 4-acres.

13. Harry's Man Cave: The New Star Motel Experience

Harry's Man Cave: The New Star Motel Experience
3.0 star property
Edgemont
9.8 out of 10, Exceptional, (25 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is £103
includes taxes & fees
14 Nov - 15 Nov
Harry's Man Cave: The New Star Motel Experience

14. 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, (2 reviews)
"Very nice stay. Everything was clean and the place was really close to town. "
United States
Jack B.
The price is £194
includes taxes & fees
17 Nov - 18 Nov
Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

15. Cozy cabin retreat nestled among forest trees

Cozy cabin retreat nestled among forest trees
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (19 reviews)
"We absolutely loved our stay at this clean, cozy cabin. The hosts really went above and beyond to make sure the home is well stocked and comfortable, We are already looking forward to visiting again. "
United States
KIM
The price is £256
includes taxes & fees
16 Nov - 17 Nov
Cozy cabin retreat nestled among forest trees

16. Loft: Serene Mountain Retreat w Fireplace Pets Ok

Loft: Serene Mountain Retreat w Fireplace Pets Ok
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (16 reviews)
"Cozy and comfortable"
United States
Jaime
The price is £181
includes taxes & fees
15 Nov - 16 Nov
Loft: Serene Mountain Retreat w Fireplace Pets Ok

17. 1 King Bed | Mobil Acc RI Shwr Suite Nsmk

1 King Bed | Mobil Acc RI Shwr Suite Nsmk
Eastside
10.0 out of 10, Exceptional, (54 reviews)
"Solid spot for a short trip."
United States
Anonymous traveller
The price is £62
includes taxes & fees
18 Nov - 19 Nov
1 King Bed | Mobil Acc RI Shwr Suite Nsmk

18. 1 King Bed | Mob Acc Tub Ste Nsmk Micfridg

1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
Eastside
10.0 out of 10, Exceptional, (47 reviews)
"Good wifi, decent pool, comfy beds."
United States
Anonymous traveller
The price is £62
includes taxes & fees
18 Nov - 19 Nov
1 King Bed | Mob Acc Tub Ste Nsmk Micfridg

19. Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3

Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Valle De Los Caballos
9.8 out of 10, Exceptional, (9 reviews)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
United States
Chloe D.
The price is £252
includes taxes & fees
16 Nov - 17 Nov
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3

20. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (56 reviews)
"Spacious rooms with air conditioning and a cozy bathtub."
United States
Anonymous traveller
The price is £72
includes taxes & fees
18 Nov - 19 Nov
2 Queen Beds | Non-Smoking, Micfridge
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.
Save an average of 15% on thousands of hotels when you're signed in

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 £82 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 offers a fireplace, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. 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 Windridge Manor - Wine Country Retreat w/ 6 Beds, Garden, Pool, Games & BBQ.

How many holiday rentals will I find in Winchester?

Choose from 35 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.