Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

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, (98 reviews)
"the room was very cozy!! the host amazing. I would definitely stay again"
United States
Isabel
The price is CA $64
CA $165 total
includes taxes & fees
Nov 16 - Nov 17
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)
"Beautiful property. Worked wonderfully for our quick girls getaway to wine country. I would definitely stay here again. Thank you Cheri!"
United States
Sara G.
The price is CA $262
CA $272 total
includes taxes & fees
Nov 17 - Nov 18
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
A resort with multiple swimming pools, palm trees, and a mountainous backdrop.

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 CA $214
CA $252 total
includes taxes & fees
Nov 15 - Nov 16
The Cottages at Golden Village Palms RV Resort
A pool surrounded by various potted plants and rocks.

4. 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 CA $193
CA $332 total
includes taxes & fees
Nov 16 - Nov 17
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
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 CA $276
CA $573 total
includes taxes & fees
Nov 15 - Nov 16
Western Horizon Home
A log cabin-style kitchen with wooden cabinets, a stainless steel refrigerator, and a granite countertop.

6. 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 CA $181
CA $199 total
includes taxes & fees
Dec 1 - Dec 2
Idyllwild Realty Vacations
A modern lobby with a reception desk, seating area, and large windows offering a view.

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 CA $107
CA $118 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Non-Smoking, Micfridge
Two white wicker chairs with yellow cushions in an outdoor setting with hanging plants and a pergola.

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 CA $318
CA $536 total
includes taxes & fees
Nov 16 - Nov 17
Romantic, private and surrounded by best Wineries!
A modern hotel room with a large bed, built-in seating, a desk, and a TV.

9. 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 CA $114
CA $126 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Non-Smoking
Outdoor spa tub

10. 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 CA $244
CA $576 total
includes taxes & fees
Dec 7 - Dec 8
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.

11. 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, (73 reviews)
"Great property. Worked out perfectly for our group in town for a wedding."
United States
Melissa F.
The price is CA $512
CA $1,083 total
includes taxes & fees
Nov 15 - Nov 16
Private modern barn custom home, mini golf, ping pong.Best location.
A swimming pool with a pink flamingo float, a covered seating area, and a modern outdoor structure.

12. 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 CA $426
CA $738 total
includes taxes & fees
Nov 17 - Nov 18
Romantic Villa • Pool • Surrounded by Wineries
Two red Adirondack chairs facing each other with a wooden cabin in the background.

13. 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 CA $192
CA $322 total
includes taxes & fees
Nov 17 - Nov 18
Tranquil Studio at Eagle Creek
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

14. 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 CA $163
CA $194 total
includes taxes & fees
Nov 13 - Nov 14
Harry's Man Cave: The New Star Motel Experience
A modern lobby with a reception desk, seating area, and large windows offering a view.

15. 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 CA $107
CA $118 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Mobil Acc RI Shwr Suite Nsmk
A modern lobby with a reception desk, seating area, and large windows.

16. 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 CA $124
CA $136 total
includes taxes & fees
Nov 15 - Nov 16
2 Queen Beds | Non-Smoking, Micfridge
A hammock and two chairs set up in a forested area with string lights.

17. 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 CA $145
CA $334 total
includes taxes & fees
Nov 22 - Nov 23
Loft: Serene Mountain Retreat w Fireplace Pets Ok
A modern lobby with a reception desk, seating area, and large windows offering a view.

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 CA $107
CA $118 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
A wooden cabin with a staircase, a covered porch, and a garden with various plants.

19. 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 CA $248
CA $476 total
includes taxes & fees
Nov 16 - Nov 17
Cozy cabin retreat nestled among forest trees
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.

20. Temecula Wine Country Stone Creek Ranch

Temecula Wine Country Stone Creek Ranch
Temecula
9.2 out of 10, Wonderful, (69 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.
The price is CA $415
CA $726 total
includes taxes & fees
Nov 17 - Nov 18
Temecula Wine Country Stone Creek Ranch
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

A hotel lobby with a checkered floor, two sofas, a small table, and a refrigerator stocked with beverages.
Hampton Inn And Suites Hemet

Hampton Inn And Suites Hemet

Hampton Inn And Suites Hemet
Hemet

10/10 Excellent

Excellent service very clean only problem was the burnt toast. It would have been nice if we had gotten a call telling us what the alarm was for. Kristen was excellent very helpful.
Canada
Alma
Reviewed November 2, 2025
Hampton Inn And Suites Hemet

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $63 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 vacation 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 vacation.

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 vacation rentals in Winchester?

Yes, you can find vacation rentals near well known sights in Winchester, or you can choose a secluded option if you're looking for relaxation. Winchester is known for its wineries and coffeehouses. Make sure you have time to check out the bars while you're in the area.

What's the top vacation rental in Winchester?

Idyllwild Realty Vacations: Located near Winchester, this vacation home rental offers a fireplace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite 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 vacation rentals will I find in Winchester?

Choose from 35 Expedia vacation rentals in Winchester for a memorable vacation.

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 larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private properties you can stay in for a short or long stay in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.