𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Winchester

Pet friendly

Apartment

Condo

Pool

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Winchester hotels

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

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.

1. The Lodge at Roseburg

Roseburg

James

S$188

includes taxes & fees

16 Oct - 17 Oct

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.

A Hampton Inn & Suites with a 'WELCOME' sign, stone facade, and a covered entrance.

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

2. Hampton Inn & Suites Roseburg

Roseburg

Dawn

S$222

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

3. Riverfront Inn Roseburg

Roseburg

Krista

S$128

includes taxes & fees

12 Oct - 13 Oct

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

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

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

An outdoor patio with wicker furniture, a round table, and umbrellas.

4. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

S$206

includes taxes & fees

8 Nov - 9 Nov

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

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

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 blue sofa, a matching armchair, and a coffee table. There are two side tables with lamps, a fireplace, and a large window providing natural light.

5. Comfort Inn Roseburg

Roseburg

Wilton

S$145

includes taxes & fees

1 Nov - 2 Nov

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

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.

A modern kitchen with granite countertops, wooden cabinets, and a coffee station.

6. Best Western Garden Villa Inn

Roseburg

Dan

S$137

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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.

7. SureStay by Best Western Roseburg

Roseburg

Kimberly

S$137

includes taxes & fees

18 Oct - 19 Oct

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

Two electric vehicle charging stations mounted on a metal stand with a concrete wall in the background.

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

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

8. Super 8 by Wyndham Roseburg

Roseburg

Elena

S$102

includes taxes & fees

8 Nov - 9 Nov

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 hotel room with a desk, chair, two lamps, a large mirror, a kitchenette with a microwave, and a striped carpet.

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

9. Quality Inn Central Roseburg

Roseburg

Rachel

S$112

includes taxes & fees

11 Nov - 12 Nov

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 6-story motel with a covered parking area and a prominent '6' sign.

10. Motel 6 Roseburg, OR

Roseburg

david

S$84

includes taxes & fees

2 Nov - 3 Nov

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.

11. Howard Johnson by Wyndham Roseburg

Roseburg

Susan

S$85

includes taxes & fees

9 Nov - 10 Nov

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

An indoor swimming pool with clear water, tiled walls, and windows.

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

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

12. Best Western Plus Hartford Lodge

Sutherlin

Danielle

S$177

includes taxes & fees

1 Nov - 2 Nov

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

Harlen

S$122

includes taxes & fees

12 Oct - 13 Oct

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 backyard with a hammock, a statue, a stone bench, and a red umbrella.

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

14. Historical John Rast House

Roseburg

Michael

S$226

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A motel with a large parking lot, a swimming pool, and a building with a sloped roof.

15. Rosewood Inn and Suites

Roseburg

Laura

S$84

includes taxes & fees

13 Oct - 14 Oct

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

A room with a large bay window, a wooden chair, a small table with a glass, and a view of a landscape.

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

16. C.H. Bailey House

Roseburg

RaShel

S$236

includes taxes & fees

1 Nov - 2 Nov

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

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

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

17. Bell Sister Flats

Roseburg

Daniel

S$496

includes taxes & fees

12 Oct - 13 Oct

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.

18. Safari Inn

Winston

SHERIE A

S$97

includes taxes & fees

13 Oct - 14 Oct

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

A room with two beds, a wooden ceiling, a small desk with a TV, and a staircase.

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

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

19. The Ranch Motel

Oakland

Jillian

S$99

includes taxes & fees

2 Nov - 3 Nov

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.

20. Motel 6 Sutherlin, OR

Sutherlin

Brian

S$78

includes taxes & fees

19 Oct - 20 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

SureStay by Best Western Roseburg

8/10 Good

"This motel is a great place for people to stay multiple days. They are pet friendly. Accommodations are average. Breakfast is sufficient. Prices are reasonable. Some minor maintenance fixes are needed. Location is good with shopping closeby. I would stay there again"

Quality Inn Central Roseburg

8/10 Good

"For the hot water and coffee wasn’t hot enough"

Comfort Inn Roseburg

10/10 Excellent

"Nice room, little cute hotel. Nothing fancy but everything worked and the people there were nice. Plus free breakfast."

Best Western Garden Villa Inn

8/10 Good

"Staff was excellent, helpful & very friendly. Ice machine was out in the parking lot away from the hotel. Breakfast was delicious. The one negative we had was there was not a cable guide for the TV. Unfortunately, I forgot to request a first floor room due to my mobility issues. When we got to the hotel there were only second floor room available with no elevator. The staff transfered us to a first floor room the next morning. They gave us a room with a raised toilet & extra safety bars, which I appreciated. We will be staying there again."

The Ranch Motel

10/10 Excellent

"The staff were so friendly and the room clean and great value Thank you"

Rice Hill Inn

10/10 Excellent

"Very good place to stay. Easy parking,"

Motel 6 Roseburg, OR

10/10 Excellent

"Very convient, close to I5, with food next door."

Motel 6 Sutherlin, OR

10/10 Excellent

"zzzzz"

Howard Johnson by Wyndham Roseburg

10/10 Excellent

"Staff was more than accommodating."

More cheap stays in Winchester

Motel 6 Roseburg, OR

3100 Nw Aviation Dr Roseburg OR

S$84

2 Nov - 3 Nov

includes taxes & fees

7.8/10 Good! (1,004 reviews)

Super 8 by Wyndham Roseburg

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

S$102

8 Nov - 9 Nov

includes taxes & fees