Winchester Holidays

Photo by Betsy Wood

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Top Flight + Hotel Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
Price was €919, price is now €522 per person
€522
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Columbus (CMH) to Los Angeles (LAX)
8.4/10 Very Good! (2,680 reviews)
the staff was very nice. the photo that i saw on expedia must have been very old.. the place really needed a face lift.

Reviewed on 25 Aug 2025

Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

5 out of 5
Wilshire Montana
Price was €2,892, price is now €1,658 per person
€1,658
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Columbus (CMH) to Los Angeles (LAX)
9.2/10 Wonderful! (466 reviews)
Oceana was the perfect hotel to spend on the last leg of my trip in LA. We relaxed by the pool and walked along the beach. It's quiet and the rooms are very spacious. The design is very pleasing to the eye. Everyone was friendly and professional - special thanks to Hakeem, Leonard, and Daniel. We will be back.

Reviewed on 19 Aug 2025

Fairmont Miramar Hotel

Fairmont Miramar Hotel

5 out of 5
Wilshire Montana
Price was €1,579, price is now €940 per person
€940
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Columbus (CMH) to Los Angeles (LAX)
8.4/10 Very Good! (1,001 reviews)
Had a great time there. Loved the ambiance. Superb customer service.

Reviewed on 25 Aug 2025

Hyatt Place Glendale / Los Angeles

Hyatt Place Glendale / Los Angeles

3 out of 5
Downtown Glendale
Price was €1,021, price is now €626 per person
€626
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Columbus (CMH) to Los Angeles (LAX)
9/10 Wonderful! (1,001 reviews)
Clean and comfortable beds.

Reviewed on 25 Aug 2025

Portofino Hotel & Marina

Portofino Hotel & Marina

4 out of 5
South Redondo
Price was €1,102, price is now €677 per person
€677
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Columbus (CMH) to Los Angeles (LAX)
8.6/10 Excellent! (1,004 reviews)
Amazing staff, beautiful property, to make it perfect a shuttle to busy Hermosa parking would be ideal! We would definitely stay there again!

Reviewed on 23 Aug 2025

Top hotels in Winchester

Pala Casino Spa And Resort

Pala Casino Spa And Resort

4 out of 5
11154 Highway 76, Pala, CA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (3,780 reviews)
"They would not give me a towel at the pool without drivers license!! I had my room key for verification. I did not want to walk all the way up to my room for my license, plus I never take my drivers license to a hotel pool because I don’t want to lose it. while I was waiting for a towel, I called ..."

Reviewed on 25 Aug 2025

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Pala Casino Spa And Resort
Pala Mesa Golf Resort

Pala Mesa Golf Resort

3.5 out of 5
2001 Old Highway 395, Fallbrook, CA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (631 reviews)
"Front desk was amazing. She got me out of the lobby pretty fast and got Me Into a room with a view"

Reviewed on 24 Aug 2025

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Pala Mesa Golf Resort
South Coast Winery Resort and Spa

South Coast Winery Resort and Spa

4 out of 5
34843 Rancho California Rd, Temecula, CA
Fully refundableReserve now, pay when you stay
The price is €218 per night from 26 Aug to 27 Aug
€218
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Beautiful location amongst wine country! The rooms were very nice but the Keurig coffee pods were terrible. But everything else was wonderful! Definitely return!"

Reviewed on 24 Aug 2025

South Coast Winery Resort and Spa
See all 1,507 properties in Winchester
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 does a Winchester holiday package cost?
You'll find cheap prices from €522 on Expedia for your Winchester getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
February, September and December are the best times to search for cheap Winchester holiday packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodation.
How many days is enough for Winchester?
With a well-organised itinerary, you can easily tick off the main Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Use Expedia's handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Winchester package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights separately. Better still, you can customise your Winchester getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Winchester?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winchester trip.
How to plan a trip to Winchester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Winchester.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Winchester.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Winchester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: Once you've settled on your travel dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.