Winchester Vacation Packages 2026 from $788

Winchester flight + hotel vacation packages

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

Dorset Hotel

$788

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Southampton (SOU)

A bar/lounge and a garden are featured at this guesthouse, along with free self parking. WiFi in public areas is free. A picnic area and luggage storage are also provided.

The Q Hotel

$847

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Southampton (SOU)

This hotel features a full-service spa and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. There's a bar/lounge on site, and a coffee shop and wedding services are also provided.

Trouville Hotel by Compass Hospitality

$857

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Southampton (SOU)

A restaurant and a bar/lounge are featured at this hotel. Take the beach shuttle and relax with beach umbrellas. WiFi in public areas is free.

The Wight

$838

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Southampton (SOU)

This smoke-free guesthouse features 2 indoor pools and 2 bars/lounges. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the hot tub and free perks like full breakfast and free self parking.

Robin Hood Inn

$860

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Southampton (SOU)

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas.

Top Winchester hotels deals

The Winchester Hotel & Spa

Worthy Lane Winchester England

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$130 total

Sep 20 - Sep 21

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

Sutton Scotney Winchester England

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$126 total

Sep 13 - Sep 14

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.

Winchester Wessex Hotel by Sunday

Paternoster Row Winchester England

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$107 total

Aug 31 - Sep 1

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

Days Inn by Wyndham Winchester M3

Moto Motorway Service Area Winchester England

Free Cancellation

Reserve now, pay when you stay

$39 nightly

$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.

Marwell Hotel Winchester South

Thompson Lane Winchester England

Free Cancellation

Reserve now, pay when you stay

$60 nightly

$72 total

Sep 6 - Sep 7

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. 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.

Pet friendly

Parking included

Leonardo Hotel Southampton

1 Charlotte Place Southampton England

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$94 total

Aug 31 - Sep 1

Total with taxes and fees

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.

Free WiFi

Restaurant

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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 $788. 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.