𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

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Our top choices for Winchester hotels

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a few windows.

A hotel room with two beds, a desk, a TV, and a window with a view of trees.

A breakfast area with wooden tables and chairs, a coffee machine, a microwave, and a refrigerator.

A Super 8 hotel with a parking lot, surrounded by greenery and a clear sky.

1. Super 8 by Wyndham Roseburg

Roseburg

Shelia

S$103

includes taxes & fees

15 Sept - 16 Sept

A hotel room with two beds, a sofa, a small table, and a window with curtains.

A living room with a sofa, armchair, and a small coffee table. There is a window with curtains, a lamp, and a staircase with a green wall.

A reception desk with a modern design, a framed artwork above it, and a fire alarm on the wall.

An indoor swimming pool with two sections, a lifeguard chair, and a safety sign.

2. SureStay by Best Western Roseburg

Roseburg

Carol

S$155

includes taxes & fees

13 Sept - 14 Sept

A hotel lobby with a reception desk, seating area, and a dining section.

A Comfort Inn hotel entrance with a clear sky, parking lot, and a sign indicating a clearance of 11 feet 5 inches.

A modern living room with a sofa set, two armchairs, and a coffee table. There are two windows with blinds, a flat-screen TV mounted on the wall, and a small side table with a lamp.

A hotel lobby with a reception desk, a large clock, and a dining area with chairs and tables.

3. Comfort Inn Roseburg

Roseburg

Kevin C

S$161

includes taxes & fees

7 Sept - 8 Sept

A stone fireplace with a flat-screen TV above it, a wooden bench, and a cushioned seating area.

An indoor swimming pool with a clear view of the outside, a no diving sign, and a lifeguard duty warning sign.

An outdoor patio with stone walls, a dining area with tables and chairs, and a sofa with striped cushions.

A cozy lobby with a stone fireplace, comfortable seating, and a dining area.

4. Hampton Inn & Suites Roseburg

Roseburg

Dawn

S$263

includes taxes & fees

4 Sept - 5 Sept

A hotel entrance with a covered walkway, a brick facade, and a parking area.

A lobby with a fireplace, striped sofas, a patterned rug, and a large window with curtains.

A hotel room with a flat-screen TV, a sofa, a dining table with chairs, a kitchen area, and a lamp.

A hotel room with a bed, a TV, a desk, a microwave, a mini-fridge, a bathroom with a bathtub, a sink, and a mirror.

5. Best Western Garden Villa Inn

Roseburg

Tracy

S$154

includes taxes & fees

7 Sept - 8 Sept

A riverside park with a wooden bench and a metal grill, a stone railing, and a bridge in the background.

A garden with various plants and trees, a well-maintained lawn, and a clear sky.

A hotel room with two beds, a desk, a chair, and a TV.

A multi-story building with a curved facade, balconies, and a well-maintained lawn with trees.

6. Riverfront Inn Roseburg

Roseburg

Sylvia

S$127

includes taxes & fees

30 Aug - 31 Aug

A hotel with a modern design, featuring a covered entrance, multiple floors, and a prominent sign.

An aerial view of a campground with RV parking, a swimming pool, and a bar area.

A hotel lobby with a sofa, armchairs, a map wall, and a seating area with tables.

A hotel reception desk with a modern design, a vending machine, and a view of the outside.

7. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

S$272

includes taxes & fees

6 Sept - 7 Sept

A reception desk with a brown counter, framed pictures on the wall, and a laptop on the desk.

A clean, well-lit corridor with vending machines on one side and seating areas on the other.

A row of white washing machines in a room with wooden flooring and a brown curtain.

8. Motel 6 Roseburg, OR

Roseburg

Maria

S$107

includes taxes & fees

13 Sept - 14 Sept

A motel with a covered parking area, a fenced garden, and a sign for a nearby ATM.

A hotel room with a bed, a desk with a computer, a chair, a television, and a lamp.

A motel with a swimming pool, multiple balconies, and outdoor seating.

A hotel room with a kitchenette, a bed, a desk with a chair, and a mirror.

9. Quality Inn Central Roseburg

Roseburg

Peng

S$124

includes taxes & fees

15 Sept - 16 Sept

A patio with wicker furniture, a pond, and autumn foliage.

A hotel with a large building, a grassy area, and a river with trees and hills in the background.

A hotel lobby with a fireplace, seating area, and a kitchen area.

A stone wall with a fireplace and a wooden table with a bowl of decorative items.

10. The Lodge at Roseburg

Roseburg

Ajay

S$249

includes taxes & fees

30 Aug - 31 Aug

A hotel entrance with a glass door, a sign indicating the entrance, and a blue awning.

A hotel room with a bed, a television, a desk, a chair, a sofa, and a red wall.

A gazebo with a metal roof, surrounded by mulch and metal chairs.

A swimming pool with a blue deck, surrounded by a black fence, and a small blue building nearby.

11. Rosewood Inn and Suites

Roseburg

Harold

S$89

includes taxes & fees

13 Sept - 14 Sept

A Best Western Plus hotel with a covered parking area, stone pillars, and a variety of trees.

A hotel room with two beds, each with white bedding and red accents, a bedside lamp, and framed artwork on the walls.

A cozy living room with a stone fireplace, a piano, and a large window offering a view of trees.

A restaurant with multiple tables and chairs, a counter with coffee machines, and a television mounted on the wall.

12. Best Western Plus Hartford Lodge

Sutherlin

Harold

S$200

includes taxes & fees

13 Sept - 14 Sept

A hotel room with two beds, a desk with a television, a chair, a microwave, and a window with curtains.

A hotel room with a large bed, a desk with a computer, an air conditioning unit, and a television.

A hotel room with two beds, a desk with a chair, a television, a lamp, and a sofa.

A two-story motel with a blue roof and beige siding, featuring a parking lot and a Pepsi vending machine.

13. Umpqua Valley Hotel

Roseburg

Shannon

S$125

includes taxes & fees

30 Aug - 31 Aug

A two-story house with a porch, a flag, and a sign indicating it is for sale.

A traditional room with wooden paneling, a chandelier, and classic furniture including a red armchair and a wooden sideboard.

A cozy room with a patterned armchair, a matching ottoman, a red and white patterned rug, a wooden bookshelf, and a large window with newspapers.

A garden with various plants and flowers, a tree, and a building in the background.

14. Historical John Rast House

Roseburg

Michael

S$224

includes taxes & fees

29 Aug - 30 Aug

A covered bridge with a sign indicating a weight limit of 3 tons and a 10-foot clearance.

A compact kitchen with wooden cabinets, a microwave, and a sink. There's a dining area with a table and a lamp. A patterned rug covers the floor.

A breakfast bar with a variety of food items, including fruits, pastries, and condiments.

A reception desk with a plaque for Howard Johnson, framed certificates, and a flag.

15. Howard Johnson by Wyndham Roseburg

Roseburg

Mary

S$104

includes taxes & fees

13 Sept - 14 Sept

A glass table with wine glasses and a decorative bowl, set on a patio with a view of hills and a sofa with colorful cushions.

A sunroom with large windows, wicker furniture, a table, and a lamp.

A dining area with a table set for two, a fireplace, and a view of the outdoors.

A spacious interior with high ceilings, exposed wooden beams, and large windows. There are several wooden barrels and a glass table in the center.

16. C.H. Bailey House

Roseburg

Kuan-Ju

S$239

includes taxes & fees

9 Sept - 10 Sept

A green building with a '101 B' address sign, a 'VISA' sign, and a 'NO SOLICITORS' sign.

A hotel room with a bed, a desk with a chair, a television, a microwave, and a refrigerator.

A street with a speed limit sign, a 'No Pets Allowed' sign, and a car parked on the side.

A hotel room with two beds, a nightstand, a lamp, a window with curtains, and a painting on the wall.

17. Safari Inn

Winston

SHERIE A

S$106

includes taxes & fees

24 Sept - 25 Sept

A motel with a central entrance, a parking lot, and a large evergreen tree in the foreground.

A reception area with a brown counter, framed pictures on the wall, and a seating area with chairs and a rug.

A hotel room with two beds, a desk, a mirror, and a TV.

A room with a large window, a radiator, a table with chairs, and framed pictures on the wall.

18. Motel 6 Sutherlin, OR

Sutherlin

Ronald

S$100

includes taxes & fees

31 Aug - 1 Sept

A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

A storefront with large windows, a hanging planter with red flowers, and a street with parked cars.

A storefront with a black awning displaying the names 'Bell Sister Flats' and 'Paul L Bentley Architect A.I.A. P.C.' with contact numbers and a door marked '615'.

A modern hotel room with a large bed, a sofa, a fireplace, and a TV mounted on the wall.

19. Bell Sister Flats

Roseburg

S$473

includes taxes & fees

31 Aug - 1 Sept

A cozy interior with wooden walls, a large wooden wheel, a chandelier, and a view of the outside.

A yellow sign with the word "RANCH" in black letters, indicating a motel or lodging establishment.

A cozy room with a large wooden wheel, a table with books, and various decorative items.

A wooden staircase with a television on a wooden stand and a trash bin.

20. The Ranch Motel

Oakland

Diana

S$116

includes taxes & fees

15 Sept - 16 Sept

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Top Winchester Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

8/10 Good

"The room was clean and breakfast was pretty good!"

Rice Hill Inn

8/10 Good

"Clean room, helpful staff, plenty of parking, cold AC."

Riverfront Inn Roseburg

10/10 Excellent

"You should stay here when visiting Roseburg! All rooms have a balcony that overlooks a very pretty private park and also provides a view of the local river. The exterior is painted a clean looking dark gray, with white modern planters. I loved the special orange scented soap products available in the room. King bed was very comfortable. There was a recliner in the room and heavy light blocking curtains! Shower only. Decor was pleasant with a photo print of a waterfall, which is lovely, since we had driven the highway of waterfalls that same day. Check-in and out was pleasant. I appreciated the printed resturant recommendations. The maid and custodial staff were taking care of things on the property, like cleaning freshly blown leaves out of the pool. The pool is a good size and was refreshing, but shows some aging. I would have liked some plants or decor in pool area. Even though the hotel is on a loud intersection, it was quiet in the room."

The Ranch Motel

10/10 Excellent

"Es la segunda Vez que viajo y rento el hotel, me gusta"

Motel 6 Sutherlin, OR

8/10 Good

"Had issues with the microwave, but otherwise a good night’s stay."

Quality Inn Central Roseburg

10/10 Excellent

"This was a great place to stay! The room was so nice and big. The place is so cozy and beautiful. It’s maintained well. The staff is amazing!! Such helpful welcoming and fun staff! We would stay here again 100%!"

SureStay by Best Western Roseburg

8/10 Good

"The staff is always very nice here! Super friendly. Breakfast was really a nice spread of hot and cold items and was very good! The cook even came out to see if we needed anything and see if everything tasted ok. We were given the option of what floor we wanted so we chose the 4th since it's the newly renovated floor. Our lights didn't work above the sink so made it difficult for 2 females to get ready w/o that lighted mirror. We did tell the staff but nobody came to fix it the entire weekend we were there. I like that there is a frig and microwave. The property is very safe. I usually like to stay here when I'm in town and will continue to do so."

Motel 6 Roseburg, OR

10/10 Excellent

"Very convenient. I have coffee!"

Safari Inn

10/10 Excellent

"Lovely motel with clean rooms, good parking and excellent staff. We will stay there again."

More cheap stays in Winchester

Motel 6 Sutherlin, OR

1400 Hospitality Way Sutherlin OR

S$100

31 Aug - 1 Sept

includes taxes & fees

7.6/10 Good! (1,007 reviews)

Super 8 by Wyndham Roseburg

3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR

S$103

15 Sept - 16 Sept

includes taxes & fees

Riverfront Inn Roseburg

315 W Harvard Ave Roseburg OR

S$127

30 Aug - 31 Aug

includes taxes & fees

8.6/10 Excellent! (1,478 reviews)

Best Western Garden Villa Inn

760 NW Garden Valley Boulevard Roseburg OR

S$154

7 Sept - 8 Sept

includes taxes & fees

8/10 Very good! (1,007 reviews)

SureStay by Best Western Roseburg

2855 NW Edenbower Blvd Roseburg OR

S$155

13 Sept - 14 Sept

includes taxes & fees

8/10 Very good! (1,013 reviews)

Holiday Inn Express & Suites Roseburg North by IHG

1530 NW Mulholland Drive Roseburg OR

S$272

6 Sept - 7 Sept

includes taxes & fees

9.8/10 Exceptional! (79 reviews)

Frequently asked questions

Where is the best place for a stay in Winchester?

Super 8 by Wyndham Roseburg, located 2.2 mi (3.6 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Riverfront Inn Roseburg and Best Western Garden Villa Inn. 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! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What's it like to stay in Winchester?

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

What are the top places to visit in Winchester?

A favourite place to visit is North Umpqua River. You'll also find Winchester Dam and Melrose Vineyards in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and February, with an average of 5°C. Average annual precipitation for Winchester is 1255 mm.

Winchester Hotels from S$89

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Super 8 by Wyndham Roseburg

2. SureStay by Best Western Roseburg

3. Comfort Inn Roseburg

4. Hampton Inn & Suites Roseburg

5. Best Western Garden Villa Inn

6. Riverfront Inn Roseburg

7. Holiday Inn Express & Suites Roseburg North by IHG

8. Motel 6 Roseburg, OR

9. Quality Inn Central Roseburg

10. The Lodge at Roseburg

11. Rosewood Inn and Suites

12. Best Western Plus Hartford Lodge

13. Umpqua Valley Hotel

14. Historical John Rast House

15. Howard Johnson by Wyndham Roseburg

16. C.H. Bailey House

17. Safari Inn

18. Motel 6 Sutherlin, OR

19. Bell Sister Flats

20. The Ranch Motel

Top Winchester Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

Rice Hill Inn

Riverfront Inn Roseburg

The Ranch Motel

Motel 6 Sutherlin, OR

Quality Inn Central Roseburg

SureStay by Best Western Roseburg

Motel 6 Roseburg, OR

Safari Inn

More cheap stays in Winchester

Motel 6 Sutherlin, OR

Super 8 by Wyndham Roseburg

Riverfront Inn Roseburg

Best Western Garden Villa Inn

SureStay by Best Western Roseburg

Holiday Inn Express & Suites Roseburg North by IHG

Frequently asked questions

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