Windsor Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Windsor holiday rentals

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
31 May - 1 Jun
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 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
1 Jun - 2 Jun
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
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
31 May - 1 Jun
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 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
31 May - 1 Jun
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Exterior

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.4 out of 10, Exceptional, (3 reviews)
"Nice camping spot "
United States
Evelyn
The price is HK$620
HK$707 total
includes taxes & fees
3 Jun - 4 Jun
The Ranch at Lake Sonoma
Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.0 out of 10, Wonderful, (106 reviews)
"Wonderful management and clean rooms, clean bathrooms. "
United States
Vrajeshkumar
The price is HK$956
HK$1,090 total
includes taxes & fees
3 Jun - 4 Jun
Wildhaven Sonoma Glamping
TV, fireplace

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Comfortable place to stay, close to everything. Host was amazing. "
United States
Joelle S.
The price is HK$1,185
HK$2,706 total
includes taxes & fees
28 May - 29 May
Tranquil Redwood Retreat
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$635
HK$1,476 total
includes taxes & fees
15 Jun - 16 Jun
Cobb Mountain Chalet King Size Suite
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$999
HK$2,191 total
includes taxes & fees
21 Jun - 22 Jun
2 Hidden Wine Country Gem Upstairs Unit
Interior

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (12 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is HK$997
HK$3,137 total
includes taxes & fees
28 May - 29 May
2BR Bungalow | Russian River & Wine Country
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$903
HK$1,910 total
includes taxes & fees
28 May - 29 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, (22 reviews)
"Nice, quiet place to stay in Sonoma. Lots of outdoor space for the kiddos. "
United States
Aaron G.
The price is HK$1,209
HK$4,041 total
includes taxes & fees
1 Jun - 2 Jun
Relaxing Vineyard View, Rooftop Deck & Game Room
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$1,171
HK$2,758 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful, charming, cottage in wine country. Beautiful yard!
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$1,826 total
includes taxes & fees
29 May - 30 May
Backyard Garden Oasis
Fridge, microwave, oven, stovetop

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is HK$1,215
HK$3,277 total
includes taxes & fees
31 May - 1 Jun
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Terrace/patio

Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (33 reviews)
"Very nice, extremely well equpped home. Very quiet with great nlback patio. Would defistay here again."
United States
Bill F.
The price is HK$1,293
HK$3,606 total
includes taxes & fees
28 May - 29 May
Somms Rest ⎮ Designed. Curated. Peaceful.
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$1,678
HK$3,565 total
includes taxes & fees
31 May - 1 Jun
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Interior

Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (20 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is HK$705
HK$1,642 total
includes taxes & fees
2 Jun - 3 Jun
Cobb Mountain Chalet Main Floor
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, (77 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is HK$2,053
HK$4,174 total
includes taxes & fees
22 Jun - 23 Jun
Glen Ellen Retreats Sunset Cottage
Beach towels

Harbor Kee Peaceful Escape By The Bay

Harbor Kee Peaceful Escape By The Bay
Bodega Bay
9.6 out of 10, Exceptional, (30 reviews)
"Beautiful property! Great location!"
United States
Kelly H.
The price is HK$1,876
HK$4,645 total
includes taxes & fees
1 Jun - 2 Jun
Harbor Kee Peaceful Escape By The Bay
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

Hotel La Rose

Hotel La Rose

6/10 Okay
"Not unclear so much as old. Like staying at grandma’s house. Also know that parking is not included, it’s an extra 15 a day in a lot half a block away."
Shari 2-night trip
Posted 1 hour ago
Hotel La Rose

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:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—BOOK 3 NIGHTS—4th FREE! Close to EVERYTHING: This holiday home rental outside of Windsor is located on the waterfront, and has a balcony, a selection of books and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 29 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.