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Windsor Holiday Rentals

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Check prices for these dates

Tonight
10 Jul - 11 Jul
Tomorrow
11 Jul - 12 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Windsor

Heart of Wine Country, Cute Cottage w/Hot Tub
Fridge, microwave, oven, stovetop

Heart of Wine Country, Cute Cottage w/Hot Tub

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay in this home although it was very brief. A great location in Windsor. "
The price is HK$2,296
HK$4,605 total
includes taxes & fees
16 Jul - 17 Jul
Heart of Wine Country, Cute Cottage w/Hot Tub
Wine Country Home of Healdsburg Wine Maker
Outdoor spa tub

Wine Country Home of Healdsburg Wine Maker

9.6 out of 10, Exceptional, (22)
"What a wonderful place to call home while on vacation!!!! Cynthia and staff are amazing and added so much to our stay. Make sure you experience the Barn tasting…it was the highlight of our trip. Property is exactly as described and the location is perfect. "
The price is HK$3,831
HK$6,999 total
includes taxes & fees
13 Jul - 14 Jul
Wine Country Home of Healdsburg Wine Maker
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (233)
"Great stay with friends! Plenty of room to spread out. Home had all the amenities and lots of charm."
The price is HK$12,952
HK$16,739 total
includes taxes & fees
24 Jul - 25 Jul
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Riverbed House with hot tub
Terrace/patio

Riverbed House with hot tub

The price is HK$1,507
HK$3,672 total
includes taxes & fees
15 Jul - 16 Jul
Riverbed House with hot tub
Love Shack private retreat
Property grounds

Love Shack private retreat

10.0 out of 10, Exceptional, (1)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
The price is HK$542
HK$1,521 total
includes taxes & fees
14 Jul - 15 Jul
Love Shack private retreat
Garden house with gas fireplace
Outdoor dining

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
The price is HK$675
HK$1,685 total
includes taxes & fees
14 Jul - 15 Jul
Garden house with gas fireplace
Tangerine Cottage spacious home
Property grounds

Tangerine Cottage spacious home

The price is HK$832
HK$2,218 total
includes taxes & fees
13 Jul - 14 Jul
Tangerine Cottage spacious home
Charming 2-bedroom cabin with Wi-Fi included in Loch Lomond
Private kitchen

Charming 2-bedroom cabin with Wi-Fi included in Loch Lomond

The price is HK$1,672
HK$2,725 total
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom cabin with Wi-Fi included in Loch Lomond
Luxury King Room with Jetted bath, Small Private Deck. Walk to Calistoga Spas
Property grounds

Luxury King Room with Jetted bath, Small Private Deck. Walk to Calistoga Spas

The price is HK$1,727
HK$2,198 total
includes taxes & fees
13 Jul - 14 Jul
Luxury King Room with Jetted bath, Small Private Deck. Walk to Calistoga Spas
Expansive 2-Room King Suite, Full Kitchen, Walk to Downtown Calistoga
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Expansive 2-Room King Suite, Full Kitchen, Walk to Downtown Calistoga

The price is HK$3,493
HK$4,488 total
includes taxes & fees
15 Jul - 16 Jul
Expansive 2-Room King Suite, Full Kitchen, Walk to Downtown Calistoga
Napa Valley Retreat in Calistoga!
Fridge, microwave, oven, stovetop

Napa Valley Retreat in Calistoga!

9.8 out of 10, Exceptional, (28)
"The place was clean and in a convenient location. Couches were uncomfortable, no cleaning supplies to wash dishes, and uncertain of check-out instructions. Minor things but a good stay over all"
The price is HK$2,975
HK$4,076 total
includes taxes & fees
24 Jul - 25 Jul
Napa Valley Retreat in Calistoga!
Cobb Mountain Chalet King Size Suite
Smart TV

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (18)
"Perfect place to stay, nice and cozy!"
The price is HK$403
HK$1,131 total
includes taxes & fees
20 Jul - 21 Jul
Cobb Mountain Chalet King Size Suite
The Parlour House at the Fainting Couch
Fridge, oven, dishwasher, coffee/tea maker

The Parlour House at the Fainting Couch

2.0 star property
The price is HK$5,868
HK$7,382 total
includes taxes & fees
30 Jul - 31 Jul
The Parlour House at the Fainting Couch
Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi
Dining

Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi

The price is HK$2,600
HK$5,510 total
includes taxes & fees
15 Jul - 16 Jul
Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi
Glen Ellen Retreat #1 Hot Tub and King Beds
Fridge, microwave, oven, stovetop

Glen Ellen Retreat #1 Hot Tub and King Beds

10.0 out of 10, Exceptional, (62)
"Great place to relax. Nice backyard with hot tub. "
The price is HK$1,319
HK$3,253 total
includes taxes & fees
15 Jul - 16 Jul
Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen Retreat #2 King Beds
Outdoor dining

Glen Ellen Retreat #2 King Beds

10.0 out of 10, Exceptional, (141)
"Excellent property."
The price is HK$1,295
HK$3,226 total
includes taxes & fees
14 Jul - 15 Jul
Glen Ellen Retreat #2 King Beds
Glen Ellen Retreat #3 King Beds
Fridge, microwave, oven, stovetop

Glen Ellen Retreat #3 King Beds

10.0 out of 10, Exceptional, (55)
"This was a wonderful place to stay and I highly recommend!"
The price is HK$1,280
HK$3,201 total
includes taxes & fees
15 Jul - 16 Jul
Glen Ellen Retreat #3 King Beds
Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country
Terrace/patio

Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country

10.0 out of 10, Exceptional, (87)
"We met family for birthday celebration. Wine tours & wonderful food! Had a great time. The kitchen was well stocked with everything needed to cook for family. Too cold for pool but enjoyed hot tub, deck and yard. Location close to all 7 wineries we visited. Highly recommend."
The price is HK$5,102
HK$8,917 total
includes taxes & fees
3 Aug - 4 Aug
Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country
LUX Private Modern Villa | Pool, Spa, & Dogs OK
Terrace/patio

LUX Private Modern Villa | Pool, Spa, & Dogs OK

The price is HK$6,908
HK$13,588 total
includes taxes & fees
14 Jul - 15 Jul
LUX Private Modern Villa | Pool, Spa, & Dogs OK
heiter house- a kenwood gem, private, hot tub with views, and centrally located
Exterior

heiter house- a kenwood gem, private, hot tub with views, and centrally located

8.0 out of 10, Very good, (1)
"We had two couples head to Napa for a short trip. Such a cute cottage and perfect for Sonoma excursions. Napa requires going over or around the mountains but it’s not bad. Hot tub was great. Cottage was well appointed. Coffee pot is on the small side for 3 coffee drinkers. No complaints. Helpful binder of info. Bedrooms were spacious. Primary bath could be updated but certainly enough room. "
The price is HK$2,671
HK$5,289 total
includes taxes & fees
13 Jul - 14 Jul
heiter house- a kenwood gem, private, hot tub with views, and centrally located
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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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?

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!: This holiday home rental outside of Windsor is located on the waterfront, and offers a selection of books, WiFi and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 40 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.