Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is NZ$639
includes taxes & fees
30 Mar - 31 Mar
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is NZ$1,776
includes taxes & fees
29 Mar - 30 Mar
Elegant Vineyard Living at a Private Wine Country Estate

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
The price is NZ$748
includes taxes & fees
30 Mar - 31 Mar
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
The price is NZ$748
includes taxes & fees
30 Mar - 31 Mar
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Windsor
The price is NZ$748
includes taxes & fees
30 Mar - 31 Mar
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (18 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is NZ$542
includes taxes & fees
30 Mar - 31 Mar
Creekside Under the Redwoods

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is NZ$542
includes taxes & fees
30 Mar - 31 Mar
Tranquil Redwood Retreat

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (5 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is NZ$657
includes taxes & fees
22 Mar - 23 Mar
2BR Bungalow | Russian River & Wine Country

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (25 reviews)
"Wonderful spot! Clean, quiet, great, shower and lovely deck. "
United States
Chloe K.
The price is NZ$257
includes taxes & fees
30 Mar - 31 Mar
Cobb Mountain Chalet King Size Suite

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is NZ$398
includes taxes & fees
18 Mar - 19 Mar
Backyard Garden Oasis

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is NZ$738
includes taxes & fees
22 Mar - 23 Mar
Russian River Retreat! Woodsy Guerneville Bungalow

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (50 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is NZ$334
includes taxes & fees
18 Mar - 19 Mar
The Tiny Tipsy Turtle

Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (74 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is NZ$867
includes taxes & fees
18 Mar - 19 Mar
Glen Ellen Retreat #3 King Beds

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (19 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is NZ$781
includes taxes & fees
31 Mar - 1 Apr
Bright and modern - Water views - Close to beach

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (15 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is NZ$855
includes taxes & fees
18 Mar - 19 Mar
Cozy Riverfront Cabin - Beach Access & Wood Stove

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is NZ$499
includes taxes & fees
29 Mar - 30 Mar
2 Hidden Wine Country Gem Upstairs Unit

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (71 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
The price is NZ$699
includes taxes & fees
30 Mar - 31 Mar
Wine Country Cottage in downtown Santa Rosa, CA

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen
10.0 out of 10, Exceptional, (83 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
The price is NZ$872
includes taxes & fees
30 Mar - 31 Mar
Glen Ellen Retreat #1 Hot Tub and King Beds

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (2 reviews)
"This is a wonderful place to stay in Sebastopol. It is comfortable, cosy, quiet and well appointed - comparable to a suite in a nice hotel. There is good access, parking and a great location. Everything worked perfectly. The only issue is that entry to the room is via a spiral stair case that would be difficult for some people with disabilities. "
United States
Joe B.
The price is NZ$424
includes taxes & fees
18 Mar - 19 Mar
Sebastopol Lux Walk toTown Guest Suite

Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley
Northwest Santa Rosa
9.8 out of 10, Exceptional, (72 reviews)
"Loved our stay!!"
United States
kristen s.
The price is NZ$921
includes taxes & fees
29 Mar - 30 Mar
Winemaker's Delight: 3BD/3BA Russian River Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$154 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Dom Whitney Tasting Lounge, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What are some of the best holiday rentals that Windsor has to offer?

Waterfront Home in Bodega Bay! 3Beds, 2Baths & panoramic ocean views.: This holiday home rental outside of Windsor is located on the beach, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windsor?

Choose from 27 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Pacific Coast Air Museum and Windsor Golf Club are other places to visit while you're in town.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.