Photo by Kim Larson

Winchester Bay holiday homes

We found 75 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:18 Dec - 25 Dec

Window view peeking thru the trees to the slough view
Front porch in the fall
Interior
Exterior detail
Exceptional
(69 reviews)

Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

Reedsport

9% off
NZ$3,561
for 7 nights, 1 cottage
NZ$509 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.
Main Living room
Private kitchen
Exceptional
(72 reviews)

CozyCattail Cabin on our secluded coastal estuary woodland retreat

Reedsport

9% off
NZ$3,208
for 7 nights, 1 cabin
NZ$458 per night
includes taxes & fees
CozyCattail Cabin on our secluded coastal estuary woodland retreat
Living area and gallery of sea-inspired art and desk with view of front yard.
Courtyard & firepit area. Main house with covered patio area (right).
Aerial view of main house, guest house, courtyard, surrounding trees and shed.
Stairs leading to the upper deck and guest house.
Exceptional
(31 reviews)

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

Lakeside

8% off
NZ$3,851
for 7 nights, 1 home
NZ$550 per night
includes taxes & fees
Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking
Interior
Property grounds
Dining
Exterior
Exceptional
(142 reviews)

Beautiful Road Access House with dock

Lakeside

8% off
NZ$2,852
for 7 nights, 1 home
NZ$407 per night
includes taxes & fees
Beautiful Road Access House with dock
Interior
Exterior
Living area
Interior
Exceptional
(192 reviews)

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

Lakeside

6% off
NZ$2,218
for 7 nights, 1 home
NZ$317 per night
includes taxes & fees
Don't Get a Room....Get a House! the Homey House
The Studio has a front row seat to incredible views. Outside lights on timer
Aframe left, Studio right. Amazing retreat! Beach is shared between homes
Enjoy the peace and tranquility of lake life!
Homes are down drive. DUNES ARE 30 SECONDS STRAIGHT AND 57 SECONDS FROM STUDIO!!
Exceptional
(48 reviews)

Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat

North Bend

9% off
NZ$3,837
for 7 nights, 1 apartment
NZ$548 per night
includes taxes & fees
Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat
Living area
Cozy, comfy and 24/7 views! Large dining table w games in the blanket chest.
Interior
Exterior
Exceptional
(33 reviews)

DUNEHAVEN AFRAME CABIN LAKEFRONT DUNE ACCESS RETREAT

North Bend

8% off
NZ$6,472
for 7 nights, 1 home
NZ$925 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:

  • Tenmile Lake (7.9 mi / 12.6 km)
  • Siltcoos Lake (14.4 mi / 23.2 km)
  • Umpqua River (4.4 mi / 7.1 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

When is the best time to visit Winchester Bay for a holiday rental?
The best time to visit Winchester Bay for a holiday rental is during the peak season from June to August, especially in July, when the weather is at its warmest and the outdoor activities are in full swing. This period draws families and adventure seekers looking to enjoy the stunning coastal scenery, with opportunities for fishing, crabbing, and beachcombing along the beautiful Oregon coast.In July, visitors can expect pleasant temperatures ranging from 15 to 25 degrees Celsius, making it ideal for sunbathing or exploring the nearby dunes and the picturesque Umpqua River. The lively option during this time means you'll find plenty of fellow travellers and opportunities for socialising at local events and festivities.For those considering a more budget-friendly option, December presents a quieter charm, superb for a peaceful getaway. While the weather can be cooler, this month allows for a great experience of coastal solitude and the chance to enjoy the beauty of winter along the shore.
What are the top attractions in Winchester Bay?
In Winchester Bay, visitors can enjoy a variety of attractions that highlight the area's natural beauty and maritime charm. The Winchester Bay Lighthouse, located near the entrance to the Umpqua River, is a picturesque spot and a popular photo opportunity. The surrounding area offers access to beautiful sandy beaches, great for relaxing or beachcombing.For those interested in outdoor activities, the nearby Umpqua National Forest provides numerous trails for hiking and opportunities for fishing and wildlife viewing. The picturesque dunes of the Oregon Dunes National Recreation Area are also a major draw, attracting those who want to explore the unique landscape or partake in activities like ATV riding and sandboarding.Additionally, the local marina offers boat rentals and fishing charters, making it easy for visitors to experience the abundant marine life off the coast.
Are all fees included in the Winchester Bay holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winchester Bay holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Winchester Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winchester Bay holiday homes?
You can find great discounts on holiday homes in Winchester Bay on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winchester Bay holiday home booking on Bookabach?
To find Winchester Bay holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Winchester Bay?
A long-stay holiday home in Winchester Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winchester Bay holiday home?
Book your Winchester Bay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winchester Bay?
Prices for holiday homes in Winchester Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winchester Bay to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.