Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Top 5 hotels in Winchester at a glance

  1. Randolph Inn and Suites — 2.5-star hotel in Winchester. Guest rating: 9.0/10 — Wonderful.
  2. Holiday Inn Express & Suites Portland by IHG — 2.5-star hotel in Portland. Guest rating: 9.2/10 — Wonderful.
  3. Baymont by Wyndham Richmond I-70 — 2.5-star hotel in Richmond. Guest rating: 8.6/10 — Excellent.
  4. Quality Inn Greenville North — 2.5-star hotel in Greenville. Guest rating: 8.2/10 — Very Good.
  5. Comfort Suites Richmond East — 2.5-star hotel in Richmond. Guest rating: 9.4/10 — Exceptional.

Where to stay in Winchester?

Golf

Randolph Inn and Suites

Randolph Inn and Suites
2.5 star property
Winchester
9.0 out of 10, Wonderful, (269 reviews)
Warm up with a morning swim at this Winchester retreat, near both golf club and speedway attractions. Free breakfast fuels your day, while fitness center workouts and convenient parking make your Indiana stay hassle-free.
The price is $108
$121 total
includes taxes & fees
Aug 5 - Aug 6
Randolph Inn and Suites
Free daily on-the-go breakfast

Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
2.5 star property
Portland
9.2 out of 10, Wonderful, (383 reviews)
This Portland business-friendly hotel offers a refreshing indoor pool and fitness center for active travelers. Relax in clean rooms with helpful staff ready to assist. Enjoy free daily breakfast and convenient parking that adds value to your stay.
The price is $110
$123 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express & Suites Portland by IHG
Room, 1 King Bed, Accessible, Non Smoking (Mobility, Bathtub w/Grab Bars) | Iron/ironing board, cribs (free), WiFi (free), bed sheets

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
2.5 star property
Richmond
8.6 out of 10, Excellent, (1,003 reviews)
Wake up to a quiet atmosphere and complimentary breakfast at this Richmond inn. The indoor pool and hot tub offer relaxation after exploring nearby attractions. Guests love the helpful staff, free WiFi, and convenient parking at this ideally located property.
The price is $76
$85 total
includes taxes & fees
Aug 23 - Aug 24
Baymont by Wyndham Richmond I-70
Room, 1 King Bed, Non Smoking, Jetted Tub | Iron/ironing board, WiFi (free), alarm clocks, bed sheets

Quality Inn Greenville North

Quality Inn Greenville North
2.5 star property
Greenville
8.2 out of 10, Very Good, (374 reviews)
The price is $102
$116 total
includes taxes & fees
Aug 29 - Aug 30
Quality Inn Greenville North
Terrace/patio

Comfort Suites Richmond East

Comfort Suites Richmond East
2.5 star property
Richmond
9.4 out of 10, Exceptional, (813 reviews)
Wake up to a free breakfast at this Richmond hotel, then spend the day exploring Hayes Arboretum or shopping at nearby Richmond Mall. After a workout in the fitness center, relax in comfortable beds with free WiFi.
The price is $97
$111 total
includes taxes & fees
Aug 30 - Aug 31
Comfort Suites Richmond East
Lobby

Surestay By Best Western Greenville

Surestay By Best Western Greenville
2.5 star property
Greenville
7.8 out of 10, Good, (427 reviews)
The price is $92
$104 total
includes taxes & fees
Aug 11 - Aug 12
Surestay By Best Western Greenville
Studio Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board (on request)

Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
2.0 star property
Centerville
6.0 out of 10, (360 reviews)
Wake up to complimentary on-the-go breakfast at this budget-friendly Centerville motel. Enjoy free WiFi and parking while exploring nearby attractions like Warm Glow Candle Company and Centerville Public Library.
The price is $63
$70 total
includes taxes & fees
Aug 16 - Aug 17
Super 8 by Wyndham Centerville-Richmond
Exterior

Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
2.0 star property
Richmond
7.0 out of 10, Good, (952 reviews)
This peaceful Richmond hotel offers a restful night's sleep with quiet rooms just minutes from Middlefork Reservoir Park. Free WiFi and parking enhance your stay, while the helpful staff at the 24-hour front desk ensures comfort throughout your visit.
The price is $54
$60 total
includes taxes & fees
Aug 16 - Aug 17
Red Roof Inn Richmond, IN
WiFi (free), bed sheets

Motel 6 Portland, IN

Motel 6 Portland, IN
2.0 star property
Portland
6.8 out of 10, (98 reviews)
Enjoy a pleasant stay at this conveniently located Portland hotel with free WiFi and parking. Clean rooms provide a restful retreat after exploring local sights. On-site laundry facilities add extra convenience for travelers.
The price is $72
$81 total
includes taxes & fees
Aug 5 - Aug 6
Motel 6 Portland, IN
Daily to-go breakfast for a fee

Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center
3.0 star property
Muncie
9.0 out of 10, Wonderful, (910 reviews)
Steps from Horizon Convention Center, this Muncie hotel offers American cuisine at 1925 PubHouse, free WiFi, and parking. Guests can visit the fitness center after exploring nearby attractions like Muncie Children's Museum and Civic Theatre.
The price is $118
$132 total
includes taxes & fees
Aug 10 - Aug 11
Courtyard Muncie at Horizon Convention Center
Standard Room, 2 Double Beds | WiFi (free), bed sheets

The Golden Inn

The Golden Inn
2.5 star property
New Paris
9.2 out of 10, Wonderful, (460 reviews)
Escape to the Golden Inn in New Paris, where free WiFi, parking, and daily housekeeping create a hassle-free stay. Close to Richmond Mall and Hayes Arboretum, this motel earns praise from travelers for its helpful staff and clean, comfortable rooms.
The price is $79
$89 total
includes taxes & fees
Aug 5 - Aug 6
The Golden Inn
Exterior

Holiday Inn Express Hotel & Suites Greenville by IHG

Holiday Inn Express Hotel & Suites Greenville by IHG
2.5 star property
Greenville
8.6 out of 10, Excellent, (340 reviews)
Conveniently located near North Park and Treaty of Greenville State Park, this hotel offers free breakfast, WiFi, and parking. Take a morning swim in the indoor pool or maintain your workout routine at the fitness center during your business trip.
The price is $119
$135 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Inn Express Hotel & Suites Greenville by IHG
Lobby

Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond
3.0 star property
New Paris
9.0 out of 10, Wonderful, (543 reviews)
This New Paris hotel offers year-round swimming in the indoor pool and relaxing sessions in the hot tub. Located near Richmond Mall and Hayes Arboretum, enjoy free breakfast, WiFi, and parking plus a 24-hour fitness center.
The price is $105
$119 total
includes taxes & fees
Aug 9 - Aug 10
Fairfield Inn by Marriott Richmond
Lobby

Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
2.5 star property
Richmond
8.6 out of 10, Excellent, (1,002 reviews)
Discover a peaceful haven in Richmond with easy interstate access. Enjoy the indoor swimming pool after a busy day, or maintain fitness routines at the on-site center. Friendly staff and complimentary breakfast earn top praise from fellow travelers.
The price is $101
$113 total
includes taxes & fees
Aug 10 - Aug 11
Best Western Plus Richmond Indiana I-70
Free daily buffet breakfast

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
2.5 star property
Richmond
9.2 out of 10, Wonderful, (991 reviews)
This Richmond hotel offers a practical 24-hour fitness center and refreshing indoor pool for year-round enjoyment. Located near Richmond Mall and Hayes Arboretum, guests appreciate the helpful staff, free breakfast, WiFi, and convenient parking.
The price is $118
$132 total
includes taxes & fees
Aug 23 - Aug 24
Hampton Inn & Suites Richmond, IN
House (1 Bedroom) | Interior

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is $108
$326 total
includes taxes & fees
Aug 6 - Aug 7
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Exterior

Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area
2.0 star property
Muncie
8.0 out of 10, Very Good, (1,003 reviews)
Located near Scheumann Stadium, this tranquil hotel offers complimentary WiFi and daily on-the-go breakfast between 6 AM and 9 AM. Free parking makes exploration convenient, while the attentive staff ensures a pleasant experience with clean, comfortable rooms.
The price is $60
$67 total
includes taxes & fees
Sep 1 - Sep 2
Super 8 by Wyndham Muncie/Ball St. College Area
Exterior

Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
3.0 star property
Richmond
9.2 out of 10, Wonderful, (463 reviews)
Conveniently located near Richmond Mall and Hayes Arboretum, this hotel offers free breakfast and parking. Take a dip in the indoor pool or hit the 24-hour fitness center after exploring local sights. Business travelers appreciate the helpful staff and practical amenities.
The price is $122
$137 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Richmond
Business center

Motel 6 Richmond, IN

Motel 6 Richmond, IN
2.0 star property
Richmond
8.2 out of 10, Very Good, (1,007 reviews)
The price is $61
$69 total
includes taxes & fees
Aug 6 - Aug 7
Motel 6 Richmond, IN
Standard Room, 1 King Bed | Desk, blackout drapes, iron/ironing board (on request), cribs (free)

Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University
2.0 star property
Muncie
6.8 out of 10, (950 reviews)
This Muncie hotel provides a peaceful night's sleep just minutes from Scheumann Stadium. Free perks include WiFi, parking, and on-the-go breakfast. The clean rooms and fitness center earn praise, with Cardinal Creek Tennis Center nearby.
The price is $53
$60 total
includes taxes & fees
Sep 2 - Sep 3
Days Inn by Wyndham Muncie -Ball State University
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.
View all properties

Top landmarks in Winchester

Winchester Speedway

7.8/10 (26 reviews)
You can catch an event at Winchester Speedway, located 2.5 mi (4 km) from central Winchester.
See properties

Check out reviews of Winchester hotels guests love

Motel 6 Richmond, IN

Motel 6 Richmond, IN

10/10 Excellent
"vl"
robert 1-night trip
Posted 22 hours ago
Motel 6 Richmond, IN

Frequently asked questions

What accommodations do travelers like in Winchester?
Guests like Randolph Inn and Suites.
Can I book a refundable accommodation in Winchester?
If you want the flexibility to change your plans to Winchester, most hotels provide refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchester if I'm looking for an affordable accommodation?
An inexpensive option worth considering is Randolph Inn and Suites.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 70°F. January and February are the coldest months when the average temperature is 33°F. May and June are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.