Winchester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Winchester Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Mission Beach
per person
22 Mar - 25 Mar
found 1 day ago
Return flight included
Hong Kong (HKG) to San Diego (SAN)
9.2/10 Wonderful! (1,299 reviews)
Have stayed at this site a few times. It is perfectly located on the beach for our needs.

Reviewed on 27 Jan,2025

Granger Hotel Gaslamp Quarter, A Member Of Design Hotels

Granger Hotel Gaslamp Quarter, A Member Of Design Hotels

4 out of 5
Downtown San Diego
per person
22 Mar - 25 Mar
found 1 day ago
Return flight included
Hong Kong (HKG) to San Diego (SAN)
9/10 Wonderful! (189 reviews)
Great location right in downtown. Walkable to everything. Ambiance was nice and staff was super welcoming. Would definitely recommend. Their breakfast was quite decent as well. They have a collaboration with the parking garage across the street.

Reviewed on 30 Jan,2025

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
per person
22 Mar - 25 Mar
found 1 day ago
Return flight included
Hong Kong (HKG) to San Diego (SAN)
8.2/10 Very Good! (1,414 reviews)
We found the location extremely convenient. We could walk to the Seaport and Sante Fe station which provided transit options to a lot of activities.

Reviewed on 28 Jan,2025

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
per person
22 Mar - 25 Mar
found 1 day ago
Return flight included
Hong Kong (HKG) to San Diego (SAN)
9/10 Wonderful! (763 reviews)
Very good location, safe

Reviewed on 28 Jan,2025

Manhattan Shores 2

Manhattan Shores 2

2.5 out of 5
Mission Beach
per person
22 Mar - 25 Mar
found 1 day ago
Return flight included
Hong Kong (HKG) to San Diego (SAN)
No reviews

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
The price is S$164 per night from 18 Feb to 19 Feb
S$164
includes taxes & fees
18 Feb - 19 Feb
8.6/10 Excellent! (2,778 reviews)
"Beautiful rooms. Nice restaurants. Friendly staff. Wish it was smoke free but that's the only downside."

Reviewed on 30 Jan,2025

Pala Casino Spa And Resort
Tahquitz Pines Retreat
Tahquitz Pines Retreat
2 out of 5
55251 S. Circle Dr, Idyllwild, CA
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 3 Feb to 4 Feb
S$129
includes taxes & fees
3 Feb - 4 Feb
9.6/10 Exceptional! (749 reviews)
"Good"

Reviewed on 29 Jan,2025

Tahquitz Pines Retreat
Hotel Xola
Hotel Xola
2.5 out of 5
24630 Sunnymead Boulevard, Moreno Valley, CA
The price is S$98 per night from 3 Feb to 4 Feb
S$98
includes taxes & fees
3 Feb - 4 Feb
7.6/10 Good! (794 reviews)
"The staff are very helpful"

Reviewed on 29 Jan,2025

Hotel Xola
See all 1,494 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 S$1,843 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.