Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cole

The Cole

3.5 out of 5
Little Tuscany
Save 100% on your flight
Price was $459, price is now $261 per person
$261
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Portland (PDX) to Los Angeles (LAX)
This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free WiFi. Self parking, express check-in, and express check-out are also offered.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was $1,205, price is now $564 per person
$564
per person
Nov 7 - Nov 9
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and laundry facilities are also provided.
Fleur Noire Hotel - 21 and Over

Fleur Noire Hotel - 21 and Over

3.5 out of 5
Uptown Design District
Price was $973, price is now $488 per person
$488
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Portland (PDX) to Los Angeles (LAX)
This smoke-free hotel features 2 restaurants, a bar/lounge, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $931, price is now $538 per person
$538
per person
Dec 12 - Dec 15
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Francisco (SFO)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the in-room fitness and perks like free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
Price was $749, price is now $434 per person
$434
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Portland (PDX) to Los Angeles (LAX)
Self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. A garden and express check-out are also provided.

Top Winchester hotels deals

Signature Temecula

Signature Temecula

3 out of 5
28980 Old Town Front St., Temecula, CA
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $90 total per night
$90 total
Oct 13 - Oct 14
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Pala Casino Spa And Resort

Pala Casino Spa And Resort

4 out of 5
11154 Highway 76, Pala, CA
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $182 total per night
$182 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a seasonal outdoor pool and a poolside bar. A terrace, a garden, and a grocery/convenience store are also on offer.
Pool
Air conditioning
Studio 6 Suites Perris, CA

Studio 6 Suites Perris, CA

2 out of 5
480 S Redlands Ave, Perris, CA
Free Cancellation
Reserve now, pay when you stay
$60 nightly
The price is $66 total per night
$66 total
Oct 12 - Oct 13
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Pet friendly
Hotel Xola

Hotel Xola

2.5 out of 5
24630 Sunnymead Boulevard, Moreno Valley, CA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $78 total per night
$78 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 3 onsite conference rooms. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
Pala Mesa Golf Resort

Pala Mesa Golf Resort

3.5 out of 5
2001 Old Highway 395, Fallbrook, CA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $173 total per night
$173 total
Oct 19 - Oct 20
Total with taxes and fees
A golf course and a restaurant are featured at this smoke-free hotel. A bar/lounge, a 24-hour front desk, and a snack bar/deli are also provided.
Pet friendly
Restaurant
South Coast Winery Resort and Spa

South Coast Winery Resort and Spa

4 out of 5
34843 Rancho California Rd, Temecula, CA
Free Cancellation
Reserve now, pay when you stay
$229 nightly
The price is $256 total per night
$256 total
Nov 3 - Nov 4
Total with taxes and fees
This Tuscan-style hotel features an attached winery, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Hot Tub
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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.

Frequently asked questions

How much are vacation packages to Winchester?
$261 is all you'll need for an exciting escape in Winchester. Bundle your hotel and flights into a Travelocity package and see how much the savings pile up. With these kinds of prices, you'll want to start packing your bags now!
How long should my Winchester vacation be?
Around 15 nights is the average amount of time travelers vacation in Winchester. But how long is right for you all depends on how many treasured memories you want to make. Why not stay a little longer and uncover some hidden gems?
Where can I get the best vacation package deals for Winchester?
One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties worldwide, it's a piece of cake to find a Winchester package deal that fits your budget.
Why should I purchase my Winchester vacation bundle with Travelocity?
Whether you're planning a weeks-long vacation or a last-minute trip, we have plenty of amazing destinations to choose from at an affordable rate. In addition, we offer 24/7 customer support, superb service and a Price Match Guarantee. Save yourself the effort and time and book your dream vacation now.
Can I save on my Winchester car rental if I combine it with hotels and flights?
With a Winchester vacation package, you can bundle your hotel, flight and car bookings and save a tidy sum. If you can't wait to uncover the best of this fantastic location, why not make a beeline for Disneyland® Resort? This top sight is 50 mi from Winchester. With your own wheels, you'll be there in no time.
Which airport is best for Winchester?
John Wayne Airport (SNA) is one of the busiest airports in Winchester. It's about 45 mi west of the downtown area. Other choices include Los Angeles - Ontario Intl. Airport (ONT) (40 mi away from central Winchester) and Palm Springs Intl. Airport (PSP) (35 mi away from central Winchester).
Where should I stay when visiting Winchester?
If you're after somewhere to spend your nights, check out the Stunning Mid Century Modern - Temecula Wine Country Oasis - Pool-Spa-Game Room-. It's the top pick for many travelers.

Photos of local treasures

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Photo by Betsy Wood
Photo by Betsy Wood