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Holiday Homes in Winchester

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester holiday homes

A swimming pool with a curved edge, surrounded by palm trees and a covered patio area with outdoor furniture.

1. 1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
9.8 out of 10, Exceptional, (95 reviews)
"Adorable stay"
United States
Alexandra
1 Bed Room Casita-Suite with Private Entrance
Living area

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
A bedroom with a bed, dresser, ceiling fan, window with blinds, door, and a mirror.

3. Private Room & Bath w/ Own Entrance- Self Check In

Private Room & Bath w/ Own Entrance- Self Check In
Hemet
Private Room & Bath w/ Own Entrance- Self Check In
A golf course with a large building and parking lot in the background.

4. Peach Blossom Country House

Peach Blossom Country House
Hemet
8.4 out of 10, Very good, (11 reviews)
"Had a wonderful stay here - perfect for my family of five. Everyone was happy with their own rooms, and having a whole house was great! We found the home clean and as advertised. Jim was responsive, and instructions were clear (especially since there’s a nearby elementary school). Wish we had more time to explore, so will definitely return when we can!"
United States
Anonymous traveller
Peach Blossom Country House
A golf course with a large building and parking lot in the background.

5. 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 €367
includes taxes & fees
29 Oct - 30 Oct
Western Horizon Home
A modern kitchen with a large stainless steel refrigerator, a dining area with a wooden table and chairs, and a staircase leading to another level.

6. Hidden Jackpot Near Soboba Casino

Hidden Jackpot Near Soboba Casino
Hemet
10.0 out of 10, Exceptional, (3 reviews)
"Had the best stay at this home, very clean, very comfortable. Irma was responsive and helpful, and we very much look forward to staying here again! It is the best place to stay in the area, as I have stayed in many different areas. Thank again! "
United States
Tyler S.
Hidden Jackpot Near Soboba Casino
A bottle of Popcorn Chardonnay, two wine glasses, a popcorn popper, and a bottle of Popfully popping corn on a kitchen counter.

7. Family Hemet Home Hot Tub + RV/Boat Parking

Family Hemet Home Hot Tub + RV/Boat Parking
Hemet
9.6 out of 10, Exceptional, (4 reviews)
"It was a Great place to stay. "
United States
FELIPE
Family Hemet Home Hot Tub + RV/Boat Parking
A vending machine with various beverage options and a payment interface.

8. 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 €75
includes taxes & fees
25 Oct - 26 Oct
1 King Bed | Mobil Acc RI Shwr Suite Nsmk
A living room with a sofa, a coffee table, a dining area with chairs, and a large window with blinds.

9. SALE! Peaceful, Clean, 4x Queen Bed, Spacious!

SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Hemet
9.4 out of 10, Exceptional, (3 reviews)
"Great affordable option for a quick overnight stay. Super close to Soboba, which was really convenient. Just be sure to bring your own towels and toiletries, as those aren’t provided."
United States
Kiana H.
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Exterior

10. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (19 reviews)
"We stayed here for one night and absolutely loved it. the cabin is new, it is beautifully decorated and has all the essentials. The area is quiet and peaceful"
United States
Rocio
The price is €146
includes taxes & fees
22 Oct - 23 Oct
Idyllwild Realty Vacations
A dirt pathway flanked by decorative vases with pampas grass, leading to a gathering area with tables and chairs, surrounded by trees and string lights.

11. Temecula Wine Country Stone Creek Ranch

Temecula Wine Country Stone Creek Ranch
Temecula
9.2 out of 10, Wonderful, (66 reviews)
"We enjoyed our stay. We loved the trails and beautiful views on the property. The house is very comfortable. It is located very close to all our favorite wineries and restaurants."
United States
Carole H.
Temecula Wine Country Stone Creek Ranch
A long dining table set for a meal with candles, placed on a terrace with a city view at night.

12. Private European Vineyard w/ Secluded Hilltop Views in Wine Country

Private European Vineyard w/ Secluded Hilltop Views in Wine Country
GlenOak Hills
9.8 out of 10, Exceptional, (18 reviews)
"House is beautiful and the view is amazing. Looking forward to staying there again. Host is great too!"
United States
Joel A.
The price is €875
includes taxes & fees
4 Nov - 5 Nov
Private European Vineyard w/ Secluded Hilltop Views in Wine Country
A pool with large rocks, lounge chairs, and mountains in the background.

13. Hilltop Wine Estate- Pickleball - Pool - 360 views

Hilltop Wine Estate- Pickleball - Pool - 360 views
Temecula
10.0 out of 10, Exceptional, (9 reviews)
"We chose to have a relaxed vacation. Pool, pickleball, made good food, lots of family games, a puzzle and some good tv. This house surpassed our expectations. We did not need to leave the property to have a great time with a big group!"
United States
Rebecca S.
Hilltop Wine Estate- Pickleball - Pool - 360 views
Outdoor spa tub

14. 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.
Rejuvenate! Remodeled home, 180-view on 4-acres.
A two-story house with a white exterior, a balcony, and a staircase leading to the upper floor.

15. Private modern barn custom home, mini golf, ping pong.Best location.

Private modern barn custom home, mini golf, ping pong.Best location.
Valle De Los Caballos
9.8 out of 10, Exceptional, (70 reviews)
"Great property. Worked out perfectly for our group in town for a wedding."
United States
Melissa F.
Private modern barn custom home, mini golf, ping pong.Best location.
A hot tub with a view of a mountainous landscape.

16. Relaxing Wine Country Stay - Hot Tub - Agave Farm

Relaxing Wine Country Stay - Hot Tub - Agave Farm
Valle De Los Caballos
10.0 out of 10, Exceptional, (17 reviews)
"The casita was very nice - clean, comfortable with a great view. Wish we could have stayed there longer."
United States
Shelley E.
The price is €398
includes taxes & fees
26 Oct - 27 Oct
Relaxing Wine Country Stay - Hot Tub - Agave Farm
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

17. Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi

Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
Lake Elsinore
9.8 out of 10, Exceptional, (7 reviews)
"The property was beautiful. The host was nice. The only thing that we did not like was the toilet seat need to be replaced…"
United States
Dawn T.
The price is €575
includes taxes & fees
27 Oct - 28 Oct
Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
An outdoor patio with a table and chairs, surrounded by lush greenery and a large umbrella with string lights.

18. Kimberly's Private Palm Château Salt Pool & Hot Tub

Kimberly's Private Palm Château Salt Pool & Hot Tub
Lake Elsinore
10.0 out of 10, Exceptional, (52 reviews)
"Wonderful stay! Sunshine, skydiving, hot tub and pool."
United States
Dean G.
The price is €456
includes taxes & fees
26 Oct - 27 Oct
Kimberly's Private Palm Château Salt Pool & Hot Tub
A living room with two grey sofas, a coffee table, and a patterned rug.

19. BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY

BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
Moreno Valley
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay , host was great and location also very calm and beautiful, recommend 10/10"
United States
Christy M.
The price is €446
includes taxes & fees
21 Oct - 22 Oct
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
A bedroom with a bed, a ceiling fan, a desk, and a TV.

20. Moana Del Sol | Vineyard Estate + Resort Pool

Moana Del Sol | Vineyard Estate + Resort Pool
Temecula
Moana Del Sol | Vineyard Estate + Resort Pool
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

Pala Casino Spa And Resort

Pala Casino Spa And Resort

10/10 Excellent
"Great customer service, everything good"
Hugo 1-night trip
Posted 3 hours ago
Pala Casino Spa And Resort

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
403
Accommodation
638 Holiday Homes
Lowest Price
€75
Highest Price
€875