Winchester Hotels from S$74

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Winchester hotel prices

Tonight
21 Nov - 22 Nov
Tomorrow night
22 Nov - 23 Nov
This weekend
22 Nov - 24 Nov
Next weekend
29 Nov - 1 Dec

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Randolph Inn and Suites
Golf
Randolph Inn and Suites
2.5 star property
9.0 out of 10, Wonderful, (204)
"Clean and neat."
The price is S$150
includes taxes & fees
27 Nov - 28 Nov
Randolph Inn and Suites
Holiday Inn Express & Suites Portland, an IHG Hotel
Lobby
Holiday Inn Express & Suites Portland, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (300)
"Very nice hotel, but not great value, very expense for and out of the way hotel. Well kept hotel, comfortable, great breakfast and snacks"
The price is S$173
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express & Suites Portland, an IHG Hotel
Motel 6 Portland, IN
Free WiFi, bed sheets
Motel 6 Portland, IN
2.0 star property
7.0 out of 10, Good, (54)
"Overall nice place with clean rooms and a great price. "
The price is S$98
includes taxes & fees
27 Nov - 28 Nov
Motel 6 Portland, IN
Hoosier Inn
Sports court
Hoosier Inn
2.5 star property
8.8 out of 10, Excellent, (104)
"Nice place, well maintained. Comfortable bed, friendly Genl Manager. "
The price is S$108
includes taxes & fees
23 Nov - 24 Nov
Hoosier Inn
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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.
Unlock Black Friday deals

Frequently asked questions

What's the best place for a stay in Winchester?

Based on our traveller data, Randolph Inn and Suites is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Two other choices for your visit to the area are Baymont by Wyndham Richmond I-70 and Baymont by Wyndham Muncie Near Ball State University. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, you'll find most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it may still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some accommodation options with pools in Winchester?

Randolph Inn and Suites: Features free breakfast, an indoor pool and free self-parking. Quality Inn and Conference Center and Best Western Classic Inn are a couple of other choices that offer an on-site pool.

What's it like staying in Winchester?

Visitors can enjoy all that Winchester has to offer, including its golf courses. In Winchester, there are 2 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Favourite places to visit include Winchester Speedway, Historic Shopping & Dining District of Winchester, Indiana and Randolph County Courthouse. Additionally, you might want to add Winchester Golf Club to your itinerary. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the seasonal weather in Winchester?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. Average annual precipitation for Winchester is 1190 mm.