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.
Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

3 out of 5
Price was $1,416, price is now $1,329 per person
$1,329
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Southampton (SOU)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Serene Riverside 6BR Luxury Retreat in Curdridge

Serene Riverside 6BR Luxury Retreat in Curdridge

3 out of 5
Price was $3,885, price is now $3,584 per person
$3,584
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Southampton (SOU)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
Southampton Getaway Huge Home Garden Sleeps 10

Southampton Getaway Huge Home Garden Sleeps 10

2 out of 5
Price was $2,532, price is now $2,356 per person
$2,356
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Southampton (SOU)
Free WiFi in public areas and a garden are available at this vacation home.
Orange Grove Hotel & Gardens

Orange Grove Hotel & Gardens

3 out of 5
Price was $1,664, price is now $1,549 per person
$1,549
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Southampton (SOU)
A restaurant and a bar/lounge are featured at this guesthouse. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop is provided and the front desk is staffed around-the-clock.
Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
The Polygon
Price was $1,456, price is now $1,378 per person
$1,378
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Southampton (SOU)
A restaurant and a bar/lounge are featured at this hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A coffee shop, dry cleaning, and luggage storage are also on offer.

Top Winchester hotels deals

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $121 total per night
$121 total
Aug 9 - Aug 10
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and laundry service. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Pool
Hot Tub
Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney Winchester England
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $115 total per night
$115 total
Aug 23 - Aug 24
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Enjoy the gym and perks like free self parking.
Pool
Spa
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Paternoster Row Winchester England
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $107 total per night
$107 total
Aug 2 - Aug 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way, Morn Hill Winchester England
Free Cancellation
$108 nightly
The price is $129 total per night
$129 total
Aug 23 - Aug 24
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and laundry facilities.
Hot Tub
Spa
Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane Winchester England
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $84 total per night
$84 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, luggage storage, and wedding services are also on offer.
Pool
Pet friendly
Days Inn by Wyndham Winchester M3

Days Inn by Wyndham Winchester M3

2.5 out of 5
Moto Motorway Service Area Winchester England
Free Cancellation
Reserve now, pay when you stay
$39 nightly
The price is $47 total per night
$47 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A garden, a picnic area, and express check-in are also on offer.
Pet friendly
Parking included
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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.

Stay near popular Winchester attractions

A historic cathedral with tall spires and large stained glass windows.

Winchester Cathedral

9.4/10 (713 reviews)
After visiting Winchester Cathedral, make a plan to see the other sights and activities in Winchester. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
Your travel dreams can become a reality in Winchester for as low as $1,329. Our vacation packages include flights and hotels, so booking your trip will be nice and easy. The only thing you'll need to worry about is having a good time.
How long should my Winchester vacation be?
There are no rules for how long your vacation in Winchester should be, but the majority of people decide to stay around 3 nights. Got some leeway with your departure date? Extend your escape by an extra night or two. That way, you'll have loads of time to explore the area's hidden gems too.
Where can I get the best vacation package deals for Winchester?
Find your dream escape at Travelocity. With access to 400 airlines and 1,000,000 properties around the world, selecting the ultimate Winchester package deal couldn't be simpler.
Why should I book my Winchester vacation bundle via Travelocity?
By booking your flights, hotel, car rental and activities altogether, you'll save big bucks as well as precious time. We have round-the-clock customer support, and you'll know that you'll always score the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book your dream getaway today and start packing!
Will I save money on my Winchester car rental if I book it with my hotel or flight?
Absolutely — combine your car, hotel and flight into a Winchester vacation package and you can save a ton. With so many things to do in the Winchester area, having your own wheels will make exploring a breeze. Once you've slid into the driver's seat, crank up the tunes and find your way to Big Ben, a must-see sight roughly 60 mi from Winchester.
Which airport is best for Winchester?
Heathrow Airport (LHR), located around 45 mi northeast of central Winchester, is probably where you'll land. Your other options are Gatwick Airport (LGW) (50 mi away from central Winchester) and Southampton Airport (SOU) (8 mi away from central Winchester).
What is there to do in Winchester?
Winchester has plenty of places to explore, including Winchester Cathedral and Winchester Christmas Market. These two popular attractions are on most visitors' travel schedules.
Where should I stay when visiting Winchester?
The St Johns Croft is the number one choice of many travelers. Book as soon as possible to avoid missing out.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.
A modern building with large windows and a dome structure.
A historic town with a prominent clock tower, narrow streets, and traditional architecture.
A brick bridge over a flowing river with a metal railing and a window with a grid pattern.
A stone building with ornate wrought iron street lamps and a large arched doorway.

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