Photo by Kim Larson

Winchester Bay holiday rentals

We found 77 holiday rentals — enter your dates for availability
Discover a selection of 15 homes and other holiday rentals in Winchester Bay that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Winchester Bay

Showing deals for:4 Dec - 11 Dec

Interior
Front porch in the fall
A rare snow day.
Exterior detail
Exceptional
(68 reviews)

Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

Reedsport

8% off
S$2,146
for 7 nights, 1 cottage
S$307 per night
includes taxes & fees
Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport
Living Room with Blue Ray Dvd player, games, books, puzzles,...
A great place to sit outside on the porch/deck to enjoy you an afternoon snack.
Cozy Cattail Cabin on a sunny July day
Private kitchen
Exceptional
(72 reviews)

CozyCattail Cabin on our secluded coastal estuary woodland retreat

Reedsport

8% off
S$2,146
for 7 nights, 1 cabin
S$307 per night
includes taxes & fees
CozyCattail Cabin on our secluded coastal estuary woodland retreat
Exterior
Property grounds
Interior
Dining
Exceptional
(141 reviews)

Beautiful Road Access House with dock

Lakeside

8% off
S$2,122
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Beautiful Road Access House with dock
Interior
Exterior
Interior
Living area
Exceptional
(191 reviews)

Don't Get a Room....Get a House! the Homey House

Lakeside

6% off
S$1,656
for 7 nights, 1 home
S$237 per night
includes taxes & fees
Don't Get a Room....Get a House! the Homey House
Kitchen area, dining areas, and cozy living room with stone fireplace & artwork.
Courtyard & firepit area. Main house with covered patio area (right).
Stairs leading to the upper deck and guest house.
Living area and gallery of sea-inspired art and desk with view of front yard.
Exceptional
(29 reviews)

Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking

Lakeside

8% off
S$2,396
for 7 nights, 1 home
S$342 per night
includes taxes & fees
Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking
Enjoy the peace and tranquility of lake life!
Aframe left, Studio right. Amazing retreat! Beach is shared between homes
The Studio has a front row seat to incredible views. Outside lights on timer
What an AMAZING VIEW from inside the Studio. Enjoy morning coffee on the patio
Exceptional
(48 reviews)

Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat

North Bend

8% off
S$2,869
for 7 nights, 1 apartment
S$410 per night
includes taxes & fees
Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat
Interior
Cozy, comfy and 24/7 views! Large dining table w games in the blanket chest.
Living area
Exterior
Exceptional
(33 reviews)

DUNEHAVEN AFRAME CABIN LAKEFRONT DUNE ACCESS RETREAT

North Bend

8% off
S$4,811
for 7 nights, 1 home
S$687 per night
includes taxes & fees
DUNEHAVEN AFRAME CABIN LAKEFRONT DUNE ACCESS RETREAT

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Winchester Bay

The parks and other outdoor surroundings create an inviting atmosphere in Winchester Bay. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Exploring the natural features in Winchester Bay

Whether you're an adventurous traveller or just want to take in the scenery, Winchester Bay is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Umpqua River (4.4 mi / 7.1 km)
  • Tenmile Lake (7.9 mi / 12.6 km)
  • Siltcoos Lake (14.4 mi / 23.2 km)
  • Umpqua Lighthouse State Park (1.5 mi / 2.4 km)
  • John Dellenback Dunes Trail (6.2 mi / 9.9 km)
  • Tahkenitch Creek Loop Trail (9.5 mi / 15.2 km)

Travelling to and around Winchester Bay

Fly into North Bend, OR (OTH-Southwest Oregon Regional), the closest airport, located 18.5 mi (29.8 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday rental in Winchester Bay?
Length of stay, season and property type are some things that can affect the price of a holiday home. Simply click on your travel dates to find your ideal fit. From cosy cabins to expansive villas, all Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Winchester Bay?
When you travel and the size and style of the property will influence the cost of your beachside stay. Type in your Winchester Bay travel dates to view your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want in your beach house.
What are the top attractions for families in Winchester Bay?
Keeping the kids entertained during your holiday in Winchester Bay is a snap with these fabulous family-friendly attractions:
  • Umpqua Lighthouse
  • Umpqua Lighthouse State Park
  • Umpqua Discovery Centre
How old do you have to be to rent a holiday rental in Winchester Bay?
The minimum age is normally 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your chosen Winchester Bay stay before booking your stay.
How long can I rent a holiday rental in Winchester Bay for?
How long you can book a holiday rental in Winchester Bay varies according to the property. Simply enter your preferred dates to view a list of options offering extended stays. With a range of amenities like laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Winchester Bay.