Winchester Holidays from £1,446

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Your Winchester Holiday

The rich history and spectacular views are just the start of the things Winchester has on offer. Experience the very best of this interesting city your way with a tailor-made Winchester holiday package. Any trip to Winchester should include some sightseeing. Hammers is a great place to kick things off. Whoever you're going away with and whatever you want to spend, your dream Winchester holiday is just a few clicks away with Expedia.

Top Winchester Flight + Hotel Deals

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

Bobby Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
20 Oct - 26 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Nashville (BNA)
9.2/10 Wonderful! (1,006 reviews)
I ended up getting a suite and it was really fun. There was enough room for all my friends to hangout. The minibar was convenient and nice. Great big shower and bed. Nice bath tub even though I don’t take baths. Overall very fun and the vibe is great.

Reviewed on 31 Jul 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
per person
20 Oct - 26 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Nashville (BNA)
9.2/10 Wonderful! (788 reviews)
Very close walk to broadway. Free car to take you into town. Beautiful clean hotel, great staff. Very happy with my stay.

Reviewed on 28 Jul 2025

Brand NEW 6 One-bedroom Units in 12south by Avantstay

3 out of 5
12 South
Save 100% on your flight
per person
4 Oct - 11 Oct
found 15 hours ago
Return flight included
London (LON) to Nashville (BNA)
No reviews
Dream Nashville, by Hyatt

Dream Nashville, by Hyatt

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Nashville (BNA)
9/10 Wonderful! (1,005 reviews)
The staff was very kind and friendly and I appreciated how they communicated with me

Reviewed on 30 Jul 2025

Fairlane Hotel

Fairlane Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
4 Oct - 11 Oct
found 15 hours ago
Return flight included
London (LON) to Nashville (BNA)
9.4/10 Exceptional! (1,000 reviews)
Staff was friendly and attentive. Rooms were spacious and quite.

Reviewed on 27 Jul 2025

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
8,500
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Tims Ford State Park, University of the South and Tims Ford Lake

Top hotels in Winchester

Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
Fully refundableReserve now, pay when you stay
The price is £102 per night from 2 Sept to 3 Sept
£102
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (619 reviews)
"Room was clean, staff were very kind and helpful. Property was quiet and well maintained. My only two minor gripes are that the coffee machine was broken both days, and there was what appeared to be mold on the bathroom ceiling. Those were small things, overall I enjoyed my stay."

Reviewed on 25 Jul 2025

Best Western Inn
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Winchester, TN
10/10 Exceptional! (46 reviews)
Family Vacation
"Our granddaughters loved the dock! Peaceful beautiful setting."

Reviewed on 2 Jul 2025

Get rates
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

2 out of 5
Winchester, TN
10/10 Exceptional! (12 reviews)
"Great house with tons of space. Highly recommend!"

Reviewed on 25 Jul 2025

Get rates
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
See all 655 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Winchester travel package cost?
Get ready to book, because a getaway to Winchester starts from only £1,446. When you bundle your flights, hotels and more into a travel package, you'll score the biggest deals.
If I'm not able to travel, can I cancel my Winchester travel package?
Because we know life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Winchester?
It's as simple as bundling. Flights, rental cars and hotels — combine whatever you need into a Winchester travel package to save loads of cash. Score even bigger bargains when you add extras such as day tours to your booking. But that's not the only impressive part. You have the freedom to customize your trip your own way. We offer over 550 airlines and 1,000,000 hotels throughout the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that suit all types of budgets, so you can jet away on that well-earned holiday now.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Winchester?
Stay where the action is. Many visitors favor hotels in the vicinity of popular sights, such as Tims Ford Marina, Hammers and Expressions.
What are the top hotels in Winchester?
If it's your first visit to Winchester, secure a room at Best Western Inn or Quality Inn Decherd / Winchester. Both have good amenities and are top options with many travellers.
How far in advance should I book my Winchester holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you can't book early, fear not. Low prices appear from time to time just weeks before departure dates.
What does an Expedia Winchester travel package include?
Flights, hotels and rental cars — we've got them covered. With Expedia, you can create your Winchester package the way you want. All you have to do is decide exactly what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the greater the savings!
What should I know before booking a Winchester travel package?
Whether it's relaxation or adventure you're after, a Winchester travel package lets you plan your escape your way. Plus, you'll score great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Winchester Expedia travel package?
With a travel package, the choice is in your hands. Whether you'd like to fly to Winchester in business or coach, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.