Windsor Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Windsor holiday rentals

A heated pool

Condo in Windsor

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43 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$1,559
HK$2,931 total
includes taxes & fees
19 Jan - 20 Jan
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining

Holiday Home in Windsor

Elegant Vineyard Living at a Private Wine Country Estate
8.4 out of 10, Very good, (6 reviews)
"Stayed here for a wedding "
United States
Lanna E.
The price is HK$4,078
HK$8,726 total
includes taxes & fees
19 Jan - 20 Jan
Elegant Vineyard Living at a Private Wine Country Estate
Front of property

Camping in Geyserville

The Ranch at Lake Sonoma
1.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Nice camping spot "
United States
Evelyn
The price is HK$463
HK$528 total
includes taxes & fees
19 Jan - 20 Jan
The Ranch at Lake Sonoma
Exterior

Mobile Home in Guerneville

Enchanting Retreat in the heart of Redwoods
8.8 out of 10, Excellent, (12 reviews)
"Beautiful, clean house nestled in the woods. Loved the hot tub and the fire pit in the AM. Super comfortable mattresses."
United States
Jennifer H.
The price is HK$1,095
HK$2,408 total
includes taxes & fees
19 Jan - 20 Jan
Enchanting Retreat in the heart of Redwoods
TV, fireplace

Mobile Home in Guerneville

Tranquil Redwood Retreat
8.8 out of 10, Excellent, (10 reviews)
"We had a lovely stay at the Tranquil Redwood Retreat! The cabin was clean, cozy, and beautifully decorated—just like the photos. The kitchen was fully stocked with everything we needed, and the check-in process was smooth and easy. It was the perfect spot for a peaceful getaway surrounded by nature. We made some great memories here and would definitely love to come back!"
United States
Stacie L.
The price is HK$1,179
HK$2,518 total
includes taxes & fees
19 Jan - 20 Jan
Tranquil Redwood Retreat
Porch

Cottage in Middletown

Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is HK$1,385
HK$1,544 total
includes taxes & fees
19 Jan - 20 Jan
Backyard Garden Oasis
Beach

Cabin in Guerneville

The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (45 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is HK$764
HK$1,503 total
includes taxes & fees
19 Jan - 20 Jan
The Tiny Tipsy Turtle
Living area

Aparthotel in Cobb

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
The price is HK$1,049
HK$2,104 total
includes taxes & fees
19 Jan - 20 Jan
Rouge Cobb Mountain Hotel - Cabin 1
Outdoor pool

Holiday Home in Scenic Brush Creek

2 Hidden Wine Country Gem Upstairs Unit
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$905
HK$2,102 total
includes taxes & fees
25 Jan - 26 Jan
2 Hidden Wine Country Gem Upstairs Unit
Meeting facility

Aparthotel in Cobb

Mandala Springs Wellness Retreat Center
3.5 star property
8.6 out of 10, Excellent, (27 reviews)
"Beautiful quiet retreat "
United States
Belwadi
Mandala Springs Wellness Retreat Center
Interior

Cottage in Guerneville

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
The price is HK$1,333
HK$3,366 total
includes taxes & fees
19 Jan - 20 Jan
Russian River Retreat! Woodsy Guerneville Bungalow
2 bedrooms, desk, iron/ironing board, free WiFi

Cottage in Santa Rosa

Wine Country Cottage in downtown Santa Rosa, CA
9.6 out of 10, Exceptional, (64 reviews)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
The price is HK$1,259
HK$2,892 total
includes taxes & fees
19 Jan - 20 Jan
Wine Country Cottage in downtown Santa Rosa, CA
Interior

Holiday Home in Cobb

Cobb Mountain Chalet Main For
9.6 out of 10, Exceptional, (14 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is HK$533
HK$1,359 total
includes taxes & fees
2 Feb - 3 Feb
Cobb Mountain Chalet Main For
Dining

Cottage in Calistoga

Comfort and Style in Our Queen Cottage
9.8 out of 10, Exceptional, (49 reviews)
"The cottage was very well appointed, very clean and comfortable. we really enjoyed our 2 night stay!Communication, check in and out were a breeze!Thank you!!"
United States
Kevin T.
The price is HK$1,240
HK$3,356 total
includes taxes & fees
19 Jan - 20 Jan
Comfort and Style in Our Queen Cottage
Fridge, microwave, oven, stovetop

Holiday Home in Northwest Santa Rosa

Wineries & Wine: A Comforting Getaway in Wine Country
9.4 out of 10, Exceptional, (22 reviews)
"This is a great location, and comfortable space for us to tour wine country! We enjoyed the condo, it was quite and clean."
United States
Gayle C.
The price is HK$850
HK$2,664 total
includes taxes & fees
19 Jan - 20 Jan
Wineries & Wine: A Comforting Getaway in Wine Country
Dining

Holiday Home in Guerneville

Cozy Riverfront Cabin - Beach Access & Wood Stove
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is HK$1,107
HK$3,905 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Riverfront Cabin - Beach Access & Wood Stove
Dining

Holiday Home in Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
10.0 out of 10, Exceptional, (6 reviews)
"Had a good time here, home is cozy and clean "
United States
James D.
The price is HK$1,170
HK$3,431 total
includes taxes & fees
20 Jan - 21 Jan
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Terrace/patio

Cottage in Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveller
The price is HK$1,941
HK$2,618 total
includes taxes & fees
19 Jan - 20 Jan
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

Aparthotel in Sebastopol

Sebastopol Lux Walk toTown Guest Suite
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 HK$1,064
HK$2,003 total
includes taxes & fees
21 Jan - 22 Jan
Sebastopol Lux Walk toTown Guest Suite
Exterior

Cottage in Calistoga

Charming King Cottage
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is HK$1,396
HK$3,571 total
includes taxes & fees
19 Jan - 20 Jan
Charming King 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

Hampton Inn & Suites Rohnert Park - Sonoma County

Hampton Inn & Suites Rohnert Park - Sonoma County

10/10 Excellent
"Great room , nice staff. "
SCOTT 1-night trip
Posted 1 day ago
Hampton Inn & Suites Rohnert Park - 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:

  • 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 30 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.