Windsor Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Windsor holiday rentals

Outdoor pool, a heated pool

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 HK$1,568
HK$2,962 total
includes taxes & fees
6 Apr - 7 Apr
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
A heated pool

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 HK$1,568
HK$2,923 total
includes taxes & fees
6 Apr - 7 Apr
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining

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 HK$3,645
HK$7,918 total
includes taxes & fees
7 Apr - 8 Apr
Elegant Vineyard Living at a Private Wine Country Estate
Outdoor pool, a heated pool

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 HK$1,568
HK$2,962 total
includes taxes & fees
6 Apr - 7 Apr
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Outdoor pool, a heated pool

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 HK$1,568
HK$2,962 total
includes taxes & fees
6 Apr - 7 Apr
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
TV, fireplace

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 HK$1,185
HK$2,508 total
includes taxes & fees
6 Apr - 7 Apr
Tranquil Redwood Retreat
Interior

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 HK$1,185
HK$2,524 total
includes taxes & fees
7 Apr - 8 Apr
Creekside Under the Redwoods
Interior

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (7 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is HK$1,009
HK$3,160 total
includes taxes & fees
8 Apr - 9 Apr
2BR Bungalow | Russian River & Wine Country
Outdoor dining

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 HK$549
HK$1,293 total
includes taxes & fees
20 Apr - 21 Apr
Cobb Mountain Chalet King Size Suite
Property grounds

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (44 reviews)
"Fabulous, beautiful and within walking distance to downtown!"
United States
Jacqui S.
The price is HK$847
HK$2,555 total
includes taxes & fees
6 Apr - 7 Apr
Private Lofted Downtown Studio
Porch

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 HK$1,638
HK$1,827 total
includes taxes & fees
10 Apr - 11 Apr
Backyard Garden Oasis
Interior

Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (67 reviews)
"We appreciated having a place to stay in Sonoma wine country and enjoyed the convenience of being close to Santa Rosa. The unit was simple and met our basic needs, though a bit more comfort would have made the Napa experience feel special. It also would have been wonderful if the host could have accommodated our early check‑in request after our long flight. The personal touch would have made our experience a bit more special on this trip."
United States
Earle I.
The price is HK$1,936
HK$5,997 total
includes taxes & fees
9 Apr - 10 Apr
Redwood Riverfront - Hot Tub and Tastings Included
Outdoor pool

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 HK$1,051
HK$2,282 total
includes taxes & fees
16 Apr - 17 Apr
2 Hidden Wine Country Gem Upstairs Unit
Outdoor dining

Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (11 reviews)
"Great stay and location!"
United States
Brandi K.
The price is HK$1,510
HK$3,185 total
includes taxes & fees
13 Apr - 14 Apr
Peaceful, charming, cottage in wine country. Beautiful yard!
Beach

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 HK$768
HK$1,511 total
includes taxes & fees
9 Apr - 10 Apr
The Tiny Tipsy Turtle
Dining

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
9.8 out of 10, Exceptional, (9 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is HK$1,568
HK$3,911 total
includes taxes & fees
6 Apr - 7 Apr
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Dining

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 HK$1,054
HK$3,819 total
includes taxes & fees
9 Apr - 10 Apr
Cozy Riverfront Cabin - Beach Access & Wood Stove
Games room

Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (19 reviews)
"What a great property! Everything was super clean. Kitchen had everything we needed. Comfortable beds. Fabulous outdoor space next to vineyards and across from a school. And, the little game room with shuffleboard and arcade game was a nice added bonus. Will definitely book again."
United States
Christina C.
The price is HK$1,939
HK$4,999 total
includes taxes & fees
10 Apr - 11 Apr
Relaxing Vineyard View, Rooftop Deck & Game Room
Smart TV

Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (37 reviews)
"Clean and comfortable place to stay, easy-check in, good amenities and location. Would definitely stay again."
United States
Scott W.
The price is HK$1,411
HK$4,175 total
includes taxes & fees
6 Apr - 7 Apr
Serenity at the Russian River
2 bedrooms, iron/ironing board, travel cot, free WiFi

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (75 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is HK$2,156
HK$4,281 total
includes taxes & fees
6 Apr - 7 Apr
Glen Ellen Retreats Sunset Cottage
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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

8/10 Good
"During our recent stay, a housekeeper entered our room unexpectedly while my partner and I were in a private moment, asking if we needed towels. This was both invasive and alarming, as we had already requested towels and room service in advance specifically to avoid any interruptions that evening. While we appreciate that the manager, Dustee, handled the situation professionally and made efforts to accommodate us afterward, the initial breach of privacy is difficult to overlook. This experience was unsettling and raised concerns about guest safety and communication protocols. The Oxford has been one of our favorite vacation destinations, which makes this situation especially disappointing. However, due to this experience, we will be postponing any future visits for the time being."
Jovontae 2-night trip
Posted 5 hours ago
Oxford Suites Sonoma County

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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 wineries and top-notch restaurants. 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. Windsor Golf Club and Pacific Coast Air Museum 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.