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.

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.

1. Hampton Inn & Suites Roseburg

Roseburg

Dawn

฿5,301

฿5,805 total

includes taxes & fees

8 Nov - 9 Nov

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.

2. The Lodge at Roseburg

Roseburg

James

฿4,496

฿4,924 total

includes taxes & fees

16 Oct - 17 Oct

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

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.

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

3. Comfort Inn Roseburg

Roseburg

Wilton

฿3,460

฿3,789 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

4. Holiday Inn Express & Suites Roseburg North by IHG

Roseburg

Ajitpal

฿4,929

฿5,397 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

Dan

฿3,278

฿3,589 total

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

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.

6. SureStay by Best Western Roseburg

Roseburg

Kimberly

฿3,274

฿3,585 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

7. Riverfront Inn Roseburg

Roseburg

Krista

฿3,295

฿3,608 total

includes taxes & fees

12 Oct - 13 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 hotel room with two beds, a desk, a TV, and a window with a view of trees.

8. Super 8 by Wyndham Roseburg

Roseburg

Elena

฿2,451

฿2,684 total

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 kitchenette, a bed, a desk with a chair, and a mirror.

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

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

9. Quality Inn Central Roseburg

Roseburg

Rachel

฿2,679

฿2,934 total

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

฿2,000

฿2,201 total

includes taxes & fees

2 Nov - 3 Nov

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.

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.

11. Best Western Plus Hartford Lodge

Sutherlin

Danielle

฿4,224

฿4,626 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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.

12. Howard Johnson by Wyndham Roseburg

Roseburg

Susan

฿2,022

฿2,214 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

13. Umpqua Valley Hotel

Roseburg

Harlen

฿2,907

฿3,184 total

includes taxes & fees

12 Oct - 13 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 motel with a large parking lot, a swimming pool, and a building with a sloped roof.

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

14. Rosewood Inn and Suites

Roseburg

Laura

฿2,179

฿2,386 total

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 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.

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

15. Historical John Rast House

Roseburg

Michael

฿4,496

฿5,929 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 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 living room with a sofa, armchair, and a small table with books and a vase. A kitchen is visible in the background with a refrigerator and microwave.

16. Bell Sister Flats

Roseburg

Daniel

฿9,517

฿12,991 total

includes taxes & fees

15 Oct - 16 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 room with a large bay window, a wooden chair, a small table with a glass, and a view of a landscape.

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

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

17. C.H. Bailey House

Roseburg

RaShel

฿6,081

฿6,172 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 hotel room with two beds, a nightstand, a lamp, a window with curtains, and a painting on the wall.

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

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

18. Safari Inn

Winston

SHERIE A

฿2,347

฿2,547 total

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 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.

19. The Ranch Motel

Oakland

Jillian

฿2,742

฿2,783 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 hotel room with two beds, a desk, a mirror, and a TV.

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

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

฿1,866

฿2,054 total

includes taxes & fees

19 Oct - 20 Oct

View all properties

Hotels recommended for families in Winchester

Hampton Inn & Suites Roseburg

Roseburg

฿5,301

฿5,805 total

includes taxes & fees

8 Nov - 9 Nov

The Lodge at Roseburg

Roseburg

฿4,496

฿4,924 total

includes taxes & fees

16 Oct - 17 Oct

Comfort Inn Roseburg

Roseburg

฿3,460

฿3,789 total

includes taxes & fees

1 Nov - 2 Nov

Best Western Garden Villa Inn

Roseburg

฿3,278

฿3,589 total

includes taxes & fees

18 Oct - 19 Oct

Super 8 by Wyndham Roseburg

Roseburg

฿2,451

฿2,684 total

includes taxes & fees

8 Nov - 9 Nov

SureStay by Best Western Roseburg

Roseburg

฿3,274

฿3,585 total

includes taxes & fees

18 Oct - 19 Oct

Riverfront Inn Roseburg

Roseburg

฿3,295

฿3,608 total

includes taxes & fees

12 Oct - 13 Oct

Quality Inn Central Roseburg

Roseburg

฿2,679

฿2,934 total

includes taxes & fees

11 Nov - 12 Nov

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Top Winchester Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

10/10 Excellent

"Nice"

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"