Windsor Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Windsor holiday rentals

Interior

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
The price is HK$1,356
HK$6,481 total
includes taxes & fees
4 May - 5 May
Windsor Home with Sauna & Outdoor Fire Pit
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
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,567
HK$2,945 total
includes taxes & fees
5 May - 6 May
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, (45 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$1,567
HK$2,945 total
includes taxes & fees
5 May - 6 May
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Pool

Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.0 out of 10, Wonderful, (4 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included
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$1,567
HK$2,945 total
includes taxes & fees
5 May - 6 May
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$1,567
HK$2,945 total
includes taxes & fees
5 May - 6 May
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Pool

Two Separate 2BR Condos w/Pool & Hot Tub

Two Separate 2BR Condos w/Pool & Hot Tub
Windsor
Two Separate 2BR Condos w/Pool & Hot Tub
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$2,499 total
includes taxes & fees
5 May - 6 May
Tranquil Redwood Retreat
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (19 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is HK$1,185
HK$2,499 total
includes taxes & fees
5 May - 6 May
Creekside Under the Redwoods
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$910
HK$2,089 total
includes taxes & fees
5 May - 6 May
2 Hidden Wine Country Gem Upstairs Unit
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (16 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is HK$1,712
HK$4,709 total
includes taxes & fees
26 May - 27 May
Cozy Riverfront Cabin - Beach Access & Wood Stove
Property grounds

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (46 reviews)
"Fabulous, beautiful and within walking distance to downtown!"
United States
Jacqui S.
The price is HK$1,869
HK$3,801 total
includes taxes & fees
5 May - 6 May
Private Lofted Downtown Studio
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is HK$557
HK$1,390 total
includes taxes & fees
5 May - 6 May
Cobb Mountain Chalet King Size Suite
Exterior

Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!

Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
Santa Rosa
9.6 out of 10, Exceptional, (23 reviews)
"Great location and property. Nikki was a great host and very responsive. We would stay here again. "
United States
Cameron K.
The price is HK$8,651
HK$13,999 total
includes taxes & fees
5 May - 6 May
Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
Outdoor dining

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (21 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is HK$1,285
HK$3,611 total
includes taxes & fees
30 Apr - 1 May
Bright and modern - Water views - Close to beach
Exterior

Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills

Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Monte Rio
9.4 out of 10, Exceptional, (19 reviews)
"Wonderfully appointed cabin in an incredibly charming location. "
United States
Shannon B.
The price is HK$1,262
HK$3,083 total
includes taxes & fees
5 May - 6 May
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Exterior

Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"I love this place. The River was going on. I wish I can go every weekend there.thank you for everything. We appreciate the owner."
United States
JOSELITA
The price is HK$839
HK$1,819 total
includes taxes & fees
30 Apr - 1 May
Rouge Cobb Mountain Hotel - Cabin 3
Games room

Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (20 reviews)
"Nice, quiet place to stay in Sonoma. Lots of outdoor space for the kiddos. "
United States
Aaron G.
Relaxing Vineyard View, Rooftop Deck & Game Room
Beach

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (53 reviews)
"Really great place. Highly recommend!!!"
United States
Jennifer
The price is HK$768
HK$1,557 total
includes taxes & fees
5 May - 6 May
The Tiny Tipsy Turtle
Exterior

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
8.6 out of 10, Excellent, (4 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 HK$987
HK$1,866 total
includes taxes & fees
5 May - 6 May
Sebastopol Lux Walk toTown Guest Suite
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

El Bonita Motel

El Bonita Motel

8/10 Good
"Nice room for old people ."
Ace 1-night trip
Posted 2 hours ago
El Bonita Motel

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?

Stunning Views of CA Coast : Beautifully Remodeled Home: This holiday home rental outside of Windsor is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Windsor?

Choose from 28 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.