Winchester Holiday Rentals, Oregon: Private House Rentals

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Our top choices for Winchester hotels

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

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

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

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

1. Hampton Inn & Suites Roseburg

Roseburg

Dawn

4.818.493 ₫

5.276.249 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

2. The Lodge at Roseburg

Roseburg

claudia

3.005.249 ₫

3.290.748 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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.

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.

3. Comfort Inn Roseburg

Roseburg

Wilton

2.671.332 ₫

2.925.108 ₫ total

includes taxes & fees

7 Nov - 8 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 modern kitchen with granite countertops, wooden cabinets, and a coffee station.

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

4. Best Western Garden Villa Inn

Roseburg

Dan

2.530.259 ₫

2.770.634 ₫ total

includes taxes & fees

26 Oct - 27 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.

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

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

5. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

3.805.095 ₫

4.166.578 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A modern building with a covered entrance, a parking lot, and autumn foliage.

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.

6. SureStay by Best Western Roseburg

Roseburg

Brian

2.527.411 ₫

2.767.515 ₫ total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

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

7. Super 8 by Wyndham Roseburg

Roseburg

Elena

1.870.191 ₫

2.047.858 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

A swimming pool with a lifeguard chair, poolside chairs, and umbrellas.

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.

8. Riverfront Inn Roseburg

Roseburg

Chris

2.543.978 ₫

2.785.485 ₫ total

includes taxes & fees

25 Oct - 26 Oct

9. Quality Inn Central Roseburg

Roseburg

Rachel

2.002.205 ₫

2.192.414 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

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

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.

10. Motel 6 Roseburg, OR

Roseburg

david

1.543.781 ₫

1.699.091 ₫ total

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 hotel room with a desk, chair, television, bed, and a bathroom with a mirror and sink.

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

11. Howard Johnson by Wyndham Roseburg

Roseburg

Susan

1.560.865 ₫

1.709.147 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

12. Rosewood Inn and Suites

Roseburg

Cameron

1.811.950 ₫

1.984.085 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

A desk with a computer, phone, and printer in a room with blue walls.

13. Umpqua Valley Hotel

Roseburg

Phuong

2.244.488 ₫

2.457.714 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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 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.

14. Best Western Plus Hartford Lodge

Sutherlin

Danielle

3.261.251 ₫

3.571.069 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

15. Historical John Rast House

Roseburg

Michael

3.124.061 ₫

4.197.397 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

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

16. Bell Sister Flats

Roseburg

Daniel

7.346.785 ₫

10.028.814 ₫ total

includes taxes & fees

21 Oct - 22 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 sunroom with large windows, wicker furniture, a table, and a lamp.

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

17. C.H. Bailey House

Roseburg

RaShel

4.694.245 ₫

4.764.658 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A small, furnished room with a television, microwave, and refrigerator, a small table with chairs, and a window with curtains.

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

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

1.811.950 ₫

1.965.966 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

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

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.

19. The Ranch Motel

Oakland

Jillian

2.116.487 ₫

2.148.235 ₫ total

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 two-story building with a patio area featuring round tables and chairs, surrounded by trees and shrubs.

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

1.440.759 ₫

1.585.715 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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Top Winchester Hotel Reviews

Umpqua Valley Hotel

10/10 Excellent

"The staff were helpful and gave suggestions. Breakfast was served and good. Alittle bit of everything to choose. Easy access to find. I would recommend it"

Rosewood Inn and Suites

8/10 Good

"The front desk was very friendly. Affordable prices"

The Lodge at Roseburg

10/10 Excellent

"Beautiful view from the balcony. Quite rooms. We had a very nice stay. Will definitely stay there again."

SureStay by Best Western Roseburg

8/10 Good

"Great stay and breakfast was delicious."

Super 8 by Wyndham Roseburg

8/10 Good

"Decent hotel. Bed was little hard"

C.H. Bailey House

10/10 Excellent

"The house was outstanding; the bed very comfortable. The room was very quiet and easy to sleep. Breakfast was delicious, presentation was great. It was an easy drive from Roseberg. I highly recommend and plan to stay next year when we return to for my wife’s high school reunion."

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."

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

1.543.781 ₫

1.699.091 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Super 8 by Wyndham Roseburg

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

1.870.191 ₫

2.047.858 ₫ total

12 Nov - 13 Nov

includes taxes & fees

7.8/10 Good! (1,003 reviews)

SureStay by Best Western Roseburg

2855 NW Edenbower Blvd Roseburg OR

2.527.411 ₫

2.767.515 ₫ total

24 Oct - 25 Oct

includes taxes & fees

8/10 Very good! (1,000 reviews)

Best Western Garden Villa Inn

760 NW Garden Valley Boulevard Roseburg OR

2.530.259 ₫

2.770.634 ₫ total

26 Oct - 27 Oct

includes taxes & fees

8/10 Very good! (1,000 reviews)

Riverfront Inn Roseburg

315 W Harvard Ave Roseburg OR

2.543.978 ₫

2.785.485 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Comfort Inn Roseburg

1539 NW Mullholland Drive Roseburg OR

2.671.332 ₫

2.925.108 ₫ total

7 Nov - 8 Nov

includes taxes & fees

Hotels in Winchester with star rating

Frequently asked questions

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.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, OR from 1.585.715 ₫

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. Hampton Inn & Suites Roseburg

2. The Lodge at Roseburg

3. Comfort Inn Roseburg

4. Best Western Garden Villa Inn

5. Holiday Inn Express & Suites Roseburg North by IHG

6. SureStay by Best Western Roseburg

7. Super 8 by Wyndham Roseburg

8. Riverfront Inn Roseburg

9. Quality Inn Central Roseburg

10. Motel 6 Roseburg, OR

11. Howard Johnson by Wyndham Roseburg

12. Rosewood Inn and Suites

13. Umpqua Valley Hotel

14. Best Western Plus Hartford Lodge

15. Historical John Rast House

16. Bell Sister Flats

17. C.H. Bailey House

18. Safari Inn

19. The Ranch Motel

20. Motel 6 Sutherlin, OR

Top Winchester Hotel Reviews

Umpqua Valley Hotel

Rosewood Inn and Suites

The Lodge at Roseburg

SureStay by Best Western Roseburg

Super 8 by Wyndham Roseburg

C.H. Bailey House

Best Western Garden Villa Inn

Howard Johnson by Wyndham Roseburg

More cheap stays in Winchester

Motel 6 Roseburg, OR

Super 8 by Wyndham Roseburg

SureStay by Best Western Roseburg

Best Western Garden Villa Inn

Riverfront Inn Roseburg

Comfort Inn Roseburg

Hotels in Winchester with star rating

Frequently asked questions

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