Winchester Holidays

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Top Flight + Hotel Deals in Winchester

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

Sonesta Nashville Airport

4 out of 5
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Nashville (BNA)
9/10 Wonderful! (1,623 reviews)
Loved the staff. The front desk help were so personable and helpful. The cleaning staff was friendly and attentive.

Reviewed on 2 Aug 2025

The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Nashville (BNA)
10/10 Exceptional! (54 reviews)
What a great find. We stayed in a four bedroom unit with full kitchen -perfect for a larger family or group. Friendly staff & high-end extras! 12 South is a beautiful area. It was great to walk to get coffee, dinner, or ice cream - not to mention the pretty murals and shopping.

Reviewed on 1 Aug 2025

Sentral Sobro

Sentral Sobro

4 out of 5
Downtown Nashville
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Nashville (BNA)
8.8/10 Excellent! (1,456 reviews)
Property was clean and quiet. Pool area was nice. Brewery was close, otherwise dining options were limited.

Reviewed on 25 Jul 2025

Placemakr Premier SoBro

Placemakr Premier SoBro

4 out of 5
Downtown Nashville
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Nashville (BNA)
9.4/10 Exceptional! (2,763 reviews)
Perfect spot for broadway. Short walk. Out balcony overlooked it, so we could sit up and people watch. Pool was nice. Garage was pricey but convenient. Everything was good besides the last nights water issue.. I get things happen, but we just didn’t have water.. was not communicated well. No showers/toilets etc.

Reviewed on 1 Aug 2025

The Printing House Hotel, Tapestry Collection By Hilton

The Printing House Hotel, Tapestry Collection By Hilton

3.5 out of 5
Downtown Nashville
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Nashville (BNA)
No reviews

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 €117 per night from 7 Aug to 8 Aug
€117
7 Aug - 8 Aug
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
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
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.

Popular places to visit

Hammers

Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.

Hammers

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from €791 on Expedia for your Winchester escape. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester holiday packages. Travelling in less busy months means you can generally find better prices on flights and accommodation.
How many days is enough for Winchester?
With a well-planned schedule, you can easily tick off the main Winchester sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Winchester trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Winchester?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winchester holiday.
How to plan a trip to Winchester?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winchester.
  2. Set your budget: Factor in costs like transportation, flights and meals when calculating how much to put aside for your trip to Winchester. Then, select a property that suits your budget, whether that's an economical stay or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Winchester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.