Winchester Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 S$143 per night from 1 Dec to 2 Dec
S$143
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (570 reviews)
"Very friendly staff! Easy check in. Very clean rooms."

Reviewed on 13 Nov,2024

Best Western Inn
The Smokehouse Lodge and Cabins
The Smokehouse Lodge and Cabins
3 out of 5
844 W Main Street, Monteagle, TN
Fully refundableReserve now, pay when you stay
The price is S$85 per night from 2 Dec to 3 Dec
S$85
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (1,016 reviews)
"We had a lovely, quintessential Tennessee stay here. Being from the UK, we absolutely loved it. The staff were great, the place is a great price and we had a great time at the restaurant with live music. Awesome stay!"

Reviewed on 19 Nov,2024

The Smokehouse Lodge and Cabins
Microtel Inn & Suites by Wyndham Manchester
Microtel Inn & Suites by Wyndham Manchester
2 out of 5
201 Expressway Dr, Manchester, TN
Fully refundableReserve now, pay when you stay
The price is S$100 per night from 27 Nov to 28 Nov
S$100
includes taxes & fees
27 Nov - 28 Nov
8.4/10 Very Good! (523 reviews)
"The room was very nice and clean. The staff were friendly and helpful with knowing of things to do in the area. Best motel coffee I have ever had. Will stay here again for sure."

Reviewed on 20 Nov,2024

Microtel Inn & Suites by Wyndham Manchester
See all 631 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.

Frequently asked questions

How much does a Winchester holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Winchester from just . And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Winchester?
Combine your flights and hotels, add extras such as tours, and save with a Winchester holiday package. You won’t just pick up impressive discounts on your getaway — you’ll have a world of choice at your fingertips too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties all over the world. Your dream holiday begins right here, right now!
Where should I stay in Winchester?
With loads to explore in Winchester, it’s a good idea to stay close to its attractions. Tims Ford Marina, Hammers and Expressions are some popular ones to put on your itinerary.
What are the top hotels in Winchester?
Book a stay at Tims Ford Lake House | Gated Community. It’s one of the area’s most popular properties. Another great option in Winchester is New Twin Creeks Marina Resort Oasis.
How far in advance should I book my Winchester holiday?
It can be hard to know exactly when the best time is to book your Winchester holiday. But usually the earlier you book, the lower the prices. In some cases, you can book your flights and hotels nearly a year prior to departure. If you’re eager to escape on a last-minute getaway, no need to stress! There are fabulous bargains popping up on Expedia every single day.
What does an Expedia Winchester travel package include?
Much of that is up to you. You can pick from a variety of Winchester bundles, such as a hotel, rental car and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you’ve made your booking, you can add on the fun stuff like tours and activities. Whatever your ideal Winchester getaway looks like, get set to save!
What should I know before booking a Winchester travel package?
When you book your flights, hotels and car rentals together, you’ll land awesome discounts. Whether you’re organising a beach escape in a villa or prefer to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Winchester Expedia holiday package?
Yes — that’s the beauty of an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines around the world, so you have options galore when organising your Winchester escape.
If I'm not able to travel, can I cancel my Winchester holiday package?
Because we know life can be unpredictable, the answer is yes. For further information, 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 without penalty. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.