Winchester Vacation Rentals from AED 165: Search Short-Term Rentals

Q: 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 .

A large industrial facility with multiple warehouses and storage tanks in a mountainous region.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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 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

Winchester

Isabel

AED 399 total

includes taxes & fees

17 Nov - 18 Nov

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

Winchester

Vanna S.

AED 634 total

includes taxes & fees

17 Nov - 18 Nov

A resort with multiple swimming pools, palm trees, and a mountainous backdrop.

3. The Cottages at Golden Village Palms RV Resort

Hemet

Albert

AED 652 total

includes taxes & fees

15 Nov - 16 Nov

4. Idyllwild Realty Vacations

Idyllwild

William

AED 516 total

includes taxes & fees

1 Dec - 2 Dec

A pool surrounded by various potted plants and rocks.

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

Valle De Los Caballos

Tina S.

AED 860 total

includes taxes & fees

16 Nov - 17 Nov

A golf course with a large building and parking lot in the background.

6. Western Horizon Home

Hemet

Taman D.

AED 1,363 total

includes taxes & fees

18 Nov - 19 Nov

A modern lobby with a reception desk, seating area, and large windows offering a view.

7. 1 King Bed | Non-Smoking, Micfridge

Eastside

Anonymous traveler

AED 303 total

includes taxes & fees

15 Nov - 16 Nov

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!

GlenOak Hills

Dana O.

AED 1,389 total

includes taxes & fees

18 Nov - 19 Nov

Two red Adirondack chairs facing each other with a wooden cabin in the background.

9. Tranquil Studio at Eagle Creek

Idyllwild-Pine Cove

"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...

Delphine

AED 830 total

includes taxes & fees

16 Nov - 17 Nov

A modern hotel room with a large bed, built-in seating, a desk, and a TV.

10. 1 King Bed | Non-Smoking

Lake Elsinore

Anonymous traveler

AED 322 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a pink flamingo float, a covered seating area, and a modern outdoor structure.

11. Romantic Villa • Pool • Surrounded by Wineries

Valle De Los Caballos

kelly s.

AED 1,987 total

includes taxes & fees

16 Nov - 17 Nov

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

Valle De Los Caballos

Scot L.

A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

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

Edgemont

CLAUDIA

AED 503 total

includes taxes & fees

15 Nov - 16 Nov

A wooden cabin with a balcony, surrounded by trees.

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

Idyllwild-Pine Cove

Jack B.

AED 931 total

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin with a staircase, a covered porch, and a garden with various plants.

15. Cozy cabin retreat nestled among forest trees

Idyllwild-Pine Cove

KIM

A hammock and two chairs set up in a forested area with string lights.

16. Loft: Serene Mountain Retreat w Fireplace Pets Ok

Idyllwild-Pine Cove

Jaime

AED 829 total

includes taxes & fees

14 Dec - 15 Dec

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

Eastside

Anonymous traveler

AED 302 total

includes taxes & fees

18 Nov - 19 Nov

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

Eastside

Anonymous traveler

AED 303 total

includes taxes & fees

15 Nov - 16 Nov

A rustic wooden cabin with a stone-paved entrance, a porch with a bench, and potted plants.

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

Valle De Los Caballos

Chloe D.

AED 1,221 total

includes taxes & fees

16 Nov - 17 Nov

A modern lobby with a reception desk, seating area, and large windows.

20. 2 Queen Beds | Non-Smoking, Micfridge

Eastside

Anonymous traveler

AED 350 total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Find vacation rentals that suit your style

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

Hemet

10/10 Excellent

Jill

A modern kitchen with a breakfast bar, a coffee machine, and a yogurt dispenser.

Holiday Inn Express & Suites Murrieta by IHG

Murrieta

10/10 Excellent

Anonymous traveler

A modern dining area with a long wooden table, multiple chairs, and pendant lighting.

Hampton Inn & Suites Murrieta Temecula

Murrieta

10/10 Excellent

The hotel is really nice, centrally located with lots of services right down the street. The breakfast is ok, it wasn't the best, but there is food if you are hungry! The only reason I didn't give the best rating for service was because the door on the side of the hotel really didn't work right and it jammed my finger pretty bad. When I told the girl at the front desk she said "yeah, it happens". That was a bummer of a response. Not, wow, sorry, can I get you ice? Or, I will have someone...

Kelley

A residential property with a well-maintained garden, a stone staircase leading to the entrance, and string lights overhead.

Inn at Churon Winery

Valle De Los Caballos

10/10 Excellent

Rafael

A hotel pool area with multiple lounge chairs and red umbrellas, surrounded by palm trees and a multi-story building.

Soboba Casino Resort

San Jacinto

10/10 Excellent

Liliana

The Cottages at Golden Village Palms RV Resort

Hemet

10/10 Excellent

Shanna

A bedroom with a bed, a wooden dresser, and a television on top of the dresser displaying a nature scene.

Private bedroom in Peach Blossom Country House

Hemet

10/10 Excellent

Robert

A table with a bottle and glasses, a potted plant, and a view of mountains.

Villa Inn-Adult Only- Temecula Wine Country

Valle De Los Caballos

10/10 Excellent

Heather

A spacious lobby with a blue carpet, seating areas, a flat-screen TV, and wall-mounted artwork.

Holiday Inn Express & Suites Beaumont - Oak Valley by IHG

Beaumont

10/10 Excellent

Sergio

A modern hotel with a curved facade, multiple floors, and a landscaped entrance area with rocks and palm trees.

Courtyard by Marriott Temecula Murrieta

Murrieta

10/10 Excellent

Sosy

A courtyard with outdoor seating, a fire pit, and string lights.

The New Inn

Valle De Los Caballos

10/10 Excellent

Lonafel

An outdoor seating area with a stone fire pit, lounge chairs, and string lights.

Staybridge Suites Temecula Wine Country by IHG

Uptown Temecula

10/10 Excellent

Elizabeth

A large pool with a covered patio area, palm trees, and a two-story building with a balcony.

South Coast Winery Resort and Spa

Valle De Los Caballos

10/10 Excellent

Jesus

An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and a small seating area.

Comfort Inn & Suites Murrieta Temecula Wine Country

Murrieta

10/10 Excellent

Lydia

A Holiday Inn Express & Suites hotel with a clear sky and palm trees.

Holiday Inn Express & Suites, Lake Elsinore by IHG

Lake Elsinore

10/10 Excellent

The bedding was amazing! Soft and comfortable for a traveler. We stayed just two nights, but we will be back, as our son and his family just moved to Lake Elsinore and we are helping them unpack and get settled. We liked this hotel so much that it will be our choice of stay again. ...

ELIZABETH

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.

Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation rentals

1. 1 Bed Room Casita-Suite with Private Entrance

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

3. The Cottages at Golden Village Palms RV Resort

4. Idyllwild Realty Vacations

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

6. Western Horizon Home

7. 1 King Bed | Non-Smoking, Micfridge

8. Romantic, private and surrounded by best Wineries!

9. Tranquil Studio at Eagle Creek

10. 1 King Bed | Non-Smoking

11. Romantic Villa • Pool • Surrounded by Wineries

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

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

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

15. Cozy cabin retreat nestled among forest trees

16. Loft: Serene Mountain Retreat w Fireplace Pets Ok

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

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

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

20. 2 Queen Beds | Non-Smoking, Micfridge

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Hampton Inn And Suites Hemet

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Winchester?

What's the top vacation rental in Winchester?

How many vacation rentals will I find in Winchester?

What can I see and do in Winchester?

What are vacation rentals like in Winchester?