6-Day England City Break in Winchester

Photo of aerial view of Winchester Cathedral and city, England.
Perfect travel plans
Everything included
Fully customizable

Description

Summary

Duration
6 days & 5 nights
Available
Jan. - Dec.
Hotel
5 nights included
Car rental
Optional
Flights
Optional
Travel app
All vouchers, itinerary, & map

Description

Take a 6-day city break in England and explore Winchester like a local. Immerse yourself in the charm of Winchester, where every corner holds a new adventure.

Experience the ultimate Winchester city break with this perfectly planned holiday package. This trip includes 5 nights in Winchester at one of the best hotels in the city. Let us take care of the details so you can fully enjoy all the attractions and activities the city has to offer. Whether you're seeking to discover the rich cultural heritage of Winchester or indulge in its delicious culinary scene, this holiday package has got you covered.

The home for your 6-day holiday in Winchester will be one of the city’s best hotels. You’ll choose from a great selection of places to stay, all conveniently located in downtown Winchester, close to many of the top attractions and best restaurants in the city. Winchester offers excellent hotels for every budget, ensuring travelers a fantastic city break. You can rest assured that we will always recommend the best available places to stay in the city.

During your vacation in Winchester, you'll get the chance to experience some of the best things to see and do in the city. Winchester Cathedral, The Great Hall, and King Alfred the Great - Statue are only a few of the many spectacular attractions and sights you’ll find on your carefully planned travel itinerary.

Maximize your holiday experience in Winchester by customizing each day with exciting tours and tickets. Whether you're tracing the footsteps of history through iconic landmarks, savoring the rich flavors of England's traditional cuisine, or uncovering the city's best-kept secrets on guided tours, Winchester promises an adventure tailored to every traveler's passion. With a diverse selection of immersive experiences to choose from, your time in Winchester is sure to be anything but ordinary.

Between sightseeing and activities, you will enjoy plenty of time to wander through Winchester's best shopping streets and markets. Let the unique souvenirs you find serve as fond reminders of your city break in England.

This travel plan is designed to include everything you need to experience the best of Winchester. By booking this vacation package, you can avoid spending hours researching and planning your city break and jump straight to enjoying it. Let the experts take care of the details so you can relax and make the most of your time in England.

To make sure the city break is fully tailored to your interests and preferences, you can easily customize each day of your journey. Our intuitive trip planning puts you in control, ensuring that every moment in Winchester reflects your unique travel style.

Book with us to get an expertly curated step-by-step travel itinerary and access to 24/7 personal travel support before, during, and after your city break in Winchester.

The best hotels, flights, activities, and tours in Winchester fill up quickly, so it's advisable to book your holiday package in advance. Select a date and start planning your city break in Winchester as early as today. Join us and discover the enchanting beauty of Winchester, England!

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Included

Hotel, 5 nights
Step-by-step guide
Personal travel agent
24/7 travel support

Destinations

Photo of aerial view of Winchester Cathedral and city, England.Winchester / 5 nights

Map

Attractions

Photo of the medieval Cathedral Church of the Holy Trinity, Saint Peter, Saint Paul and Saint Swithun, commonly known as Winchester Cathedral, in the city of Winchester, England.Winchester Cathedral
The Great Hall, Winchester, Hampshire, South East England, England, United KingdomThe Great Hall
King Alfred the Great - Statue, Winchester, Hampshire, South East England, England, United KingdomKing Alfred the Great - Statue
National Trust - Winchester City MillNational Trust - Winchester City Mill
St Catherine's Hill, HampshireSt Catherine's Hill, Hampshire
Buttercross Monument, Winchester, Hampshire, South East England, England, United KingdomButtercross Monument
Winnall Moors Nature Reserve
Winchester City Museum
Hockley Railway Viaduct, Compton and Shawford, Winchester, Hampshire, South East England, England, United KingdomHockley Railway Viaduct
Oram's ArbourOram's Arbour
The Gurkha Museum
The Royal Green Jackets (Rifles) Museum

Flights
Yes
No

Round trip
Economy
Round trip
Economy

Travel details

Flights

Round trip
Economy
Round trip
Economy
Travel dates

Include flights?

Yes
No

Travelers

Rooms

Flights

Car
Yes
No

Hotels

Personalize your itinerary

Day 1 – Winchester - arrival day

Day 1

Day 1 – Winchester - arrival day

  • Winchester - Arrival day
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  • Winnall Moors Nature Reserve
  • More

Your exciting city break begins as soon as you arrive in the beautiful city of Winchester. You’ll stay in Winchester for 5 nights.

Kick off the day at Winnall Moors Nature Reserve, a top pick for today’s sightseeing. This park is rated an average of 4.5 out of 5 stars in 404 reviews.

When the afternoon arrives, make your way to the hotel of your choice in downtown Winchester. Check-in at hotels in England normally starts around 2 to 3 PM. Each accommodation option in Winchester offers a unique blend of comfort and style in addition to prime access to the city’s top attractions.

After a full day of exploring, we recommend you try one of the best places to eat in Winchester. Enjoy the local flavors, unwind, and reflect on the day's adventures.

Book a table at The Bishop on the Bridge, Winchester, a famous dining establishment in Winchester. This culinary hotspot and its delectable cuisine have captured the hearts of food enthusiasts. Its reputation for food excellence is reflected in its 4.3 out of 5-star rating from 1,569 satisfied diners.

Another dining place you should visit in Winchester is The Wykeham Arms, Winchester, which boasts a variety of tasteful dishes that cater to different palates. It has earned a commendable 4.4 out of 5 stars, demonstrating the positive feedback from 1,272 satisfied customers.

Locals and visitors alike recommend Winchester’s The William Walker, Winchester for the delightful dining experience it gives. The establishment has garnered positive reviews for its tasty dishes, holding an admirable score of 4.4 out of 5 stars from 714 satisfied diners.

After your meal, continue your getaway at one of the hottest bars in the city, The Hampshire Bowman. This bar has an impressive average rating of 4.7 out of 5 stars by 719 customers.

Alternatively, you can grab a few shots of your favorite drink and have an amazing night at the famous Incognito. This incredible bar has a vibrant atmosphere and plays great music, worthy of its average rating of 4.7 out of 5 stars from 530 customers.

The Black Boy cannot be missed with its wide selection of alcoholic and non-alcoholic drinks. Around 1,285 bar lovers have given this place a seal of approval with their 4.6 out of 5 stars average rating.

This is the time to raise a toast for your 6-day city break in Winchester! Savor the moment and look forward to immersing yourself in the vibrant culture, stunning sights, and local delicacies of the city for the next few days to come!

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Experiences

Day 2 – Winchester

Day 2

Day 2 – Winchester

  • Winchester
  • More
  • King Alfred the Great - Statue
  • National Trust - Winchester City Mill
  • More

Get ready for another exciting day in Winchester on day 2 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 4 nights ahead, make the most of your time and create unforgettable memories in Winchester.

When you're ready to see some sights, King Alfred the Great - Statue is a great place to start with. This sightseeing destination is rated an average of 4.5 out of 5 stars by 1,552 visitors.

Another popular attraction you can visit today is National Trust - Winchester City Mill. This building has an average rating of 4.6 out of 5 stars from 920 travelers.

If you have an appetite for more adventure, check out the fantastic selection of tours and tickets offered in Winchester on this day of your trip. You'll find the most recommended ones below.

When it’s time for dinner, try one of the most popular restaurants in Winchester. Make sure to reserve a table in advance, as the best restaurants fill up quickly.

Make sure to book a table at The Hinton Arms, a popular restaurant in Winchester. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of food lovers. Its commitment to culinary excellence is evident in its 4.5 out of 5-star rating from 526 satisfied guests.

Do not miss the opportunity to dine at Overdraft Beer And Tacos during your stay in Winchester. This popular dining spot boasts a tantalizing menu, earning a remarkable rating of 4.6 out of 5 stars, esteemed by 552 satisfied guests.

Savor the flavors of The Forge, a renowned dining destination in Winchester. Offering a menu that's sure to please, it has a gained 4.6 out of 5-star rating from 547 satisfied guests.

After your meal, continue your getaway at one of the hottest bars in the city, The Bishop on the Bridge, Winchester. This bar has an impressive average rating of 4.3 out of 5 stars by 1,569 customers.

Alternatively, you can grab a few shots of your favorite drink and have an amazing night at the famous The Wykeham Arms, Winchester. This incredible bar has a vibrant atmosphere and plays great music, worthy of its average rating of 4.4 out of 5 stars from 1,272 customers.

The William Walker, Winchester cannot be missed with its wide selection of alcoholic and non-alcoholic drinks. Around 714 bar lovers have given this place a seal of approval with their 4.4 out of 5 stars average rating.

Get some rest at your hotel in preparation for another wonderful day in Winchester to come!

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Experiences

Day 3 – Winchester

Day 3

Day 3 – Winchester

  • Winchester
  • More
  • The Great Hall
  • The Gurkha Museum
  • The Royal Green Jackets (Rifles) Museum
  • More

On day 3 of your fun city break in Winchester, you’ll experience more of the best attractions and activities in the city. You now have 3 nights left in Winchester.

When you’re ready for some sightseeing, make your way to The Great Hall. This much-appreciated sightseeing destination is rated 4.4 out of 5 stars in 2,807 reviews.

Next up is The Gurkha Museum. This museum has an average rating of 4.7 out of 5 stars from 193 visitors.

Another top sightseeing recommendation is The Royal Green Jackets (Rifles) Museum. This museum has been rated 4.7 out of 5 stars in 191 reviews.

To immerse yourself in more memorable moments in Winchester, check out the best-rated tours the region offers. You can discover and choose from all of the top-rated activities you can do on this day in Winchester below.

After a full day of exploring, we recommend you try one of the best places to eat in Winchester. Enjoy the local flavors, unwind, and reflect on the day's adventures.

Make sure to reserve a table at Gurkha's Inn, an iconic dining spot in Winchester. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Its dedication to culinary innovation is evident in its 4.6 out of 5-star rating from 486 satisfied guests.

Don't miss the opportunity to enjoy culinary excellence at Greens while in Winchester. This renowned dining destination showcases an exquisite menu, distinguished with an exceptional rating of 4.6 out of 5 stars, treasured by 457 previous guests.

Delight in the culinary creations of The Globe, a favorite in Winchester. Its innovative menu offers a symphony of flavors that will tantalize your taste buds. With a reputation for excellence, it has earned a 4.4 out of 5-star rating from 485 discerning guests.

If you’re looking for a bar to end the evening at, many locals recommend The Hinton Arms, claiming it’s one of the best in the city. This bar has an average rating of 4.5 out of 5 stars from 526 customers.

Another popular place to go for a drink is The Mucky Duck. It is rated an average of 4.3 out of 5 stars by 512 customers.

The Wonston Arms Freehouse Village Pub is a place where you can easily spend an hour or two of fun or relaxation. This bar is rated an average of 4.8 out of 5 stars by 252 customers.

No matter where in Winchester you end up, an amazing evening of relaxation and enjoyment is guaranteed.

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Experiences

Day 4 – Winchester

Day 4

Day 4 – Winchester

  • Winchester
  • More
  • St Catherine's Hill, Hampshire
  • Hockley Railway Viaduct
  • More

Wake up to day 4 of your exciting city break in Winchester. You still have 2 nights left in Winchester, and we recommend that you spend this day relaxing, sightseeing, and dining at the most wonderful places the city has to offer. Here's how you can make the most of today!

Start your sightseeing with a visit to St. Catherine's Hill. This park is rated an average of 4.7 out of 5 stars from 698 visitors.

Hockley Railway Viaduct is another popular attraction you could visit today. This point of interest has a rating of 4.4 out of 5 stars from 259 visitors.

Don’t forget to check out all the popular tours and activities you can add to your travel plan. England is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

When you’re ready for dinner, we recommend you try one of the best restaurants in Winchester.

Make a reservation at Samuel's Rest, a popular dining spot in Winchester. Its reputation for being a popular dining spot shines through its 4.5 out of 5-star rating from 431 satisfied diners.

Make a reservation at The Kings Head while indulging in the charm of Winchester. This restaurant offers a delicious menu reflected with a rating of 4.3 out of 5 stars, cherished by 465 discerning connoisseurs.

Indulge in the flavors of The Eclipse Inn, a treasured establishment in Winchester. Its diverse menu promises to tantalize your palate and elevate your dining experience. Known for its exceptional service, it has earned a 4.3 out of 5-star rating from 443 satisfied guests.

Quench your thirst after a long day of adventure at Cabinet Rooms, a prime hotspot for fun and relaxation seekers in the city. Cabinet Rooms boasts an impressive 4.7 out of 5-star rating from 172 customers.

Or, try the exciting drinks at New Place Hotel, a vibrant place where locals and travelers converge for spirited toasts and amazing stories. New Place Hotel has an average rating of 4.3 out of 5 stars from 1,486 customers.

As the sun dips below the horizon, make a stop at another famous bar in the area, Overdraft Beer And Tacos. This bar is a local favorite, with an impressive rating of 4.6 out of 5-star from 1,486 customers.

Wind down and recharge for tomorrow's escapades in Winchester, England. With each day comes new experiences to cherish and enjoy.

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Experiences

Day 5 – Winchester

Day 5

Day 5 – Winchester

  • Winchester
  • More
  • Winchester Cathedral
  • Winchester City Museum
  • Buttercross Monument
  • More

As day 5 dawns in Winchester, embark on another day of exploration and adventure. Discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 1 night left, the possibilities for discovery are endless.

Seize the day by visiting some of the best attractions in the area, like Winchester Cathedral. This extraordinary anglican or episcopal cathedral has an average rating of 4.6 out of 5 stars from 8,901 visitors.

Next, make your way to Winchester City Museum. This museum is rated an average of 4.5 out of 5 stars in 261 reviews.

While in Winchester, we also recommend a visit to Buttercross Monument. This sightseeing destination has been rated an average of 4.4 out of 5 stars in 543 reviews.

To do something one-of-a-kind on this day of your trip, you can join a tour. You can discover all of the most fun and eye-opening experiences in your destination below and secure your spot here.

You have plenty of options for restaurants and bars in Winchester. So when you’re hungry or need a break from exploring, all you have to do is take your pick.

Treat yourself to a delightful dining experience at The Light of Bengal while you’re in Winchester. Famous for its lovely menu and delectable dishes, it has captivated around 170 diners, earning it an average rating of 4.5 out of 5 stars.

If you’re in the mood for a drink, visit Greens, one of the top bars in the city. An excellent place to unwind and enjoy a refreshing evening drink, Greens has earned an average rating of 4.6 out of 5 stars from 457 customers.

Alternatively, you could enjoy a toast with locals and other travelers at The Globe, a crowd-favorite. Around 485 customers have rated their experience at The Globe an average of 4.4 out of 5 stars.

Samuel's Rest belongs to the list of the best bars in Winchester, and its ratings and reviews are proof of this claim. This bar is rated an average of 4.5 out of 5 stars by 431 bar-goers.

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Winchester. Tomorrow holds new possibilities and discoveries!

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Experiences

Day 6 – Winchester - departure day

Day 6

Day 6 – Winchester - departure day

  • Winchester - Departure day
  • More
  • Oram's Arbour
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Your city break in Winchester is coming to an end, and it's soon time to say goodbye to the city. Before you leave, make sure to capture a few last moments to cherish your rejuvenating vacation in England.

Depending on how much time you have to spare on your departure day, you may want to do some last-minute shopping or sightseeing. Downtown Winchester offers excellent shopping opportunities and is the perfect place to browse for souvenirs and gifts to bring home. Take a walk and discover unique items you can purchase to remind you of your city break in Winchester.

If you would rather go for some last-minute sightseeing, the remarkable Oram's Arbour is an attraction you could visit today. This park has an average rating of 4.5 out of 5 stars from 228 visitors.

Before you conclude your city break in Winchester, drop by a top-rated restaurant for your last chance at a memorable dining experience in the city. Savor the destination's vibrant atmosphere over a delicious meal.

As you prepare to leave Winchester, remember the moments of joy, discovery, and connection you've experienced in England. Carry them with you as souvenirs of your journey, guiding you as you continue to explore and create new memories.

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Experiences

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