Photo by Jennifer Hill

Windsor Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
19 Feb - 20 Feb
Tomorrow
20 Feb - 21 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in Windsor

Cottage home near the Russian River; county parks; numerous wineries
Property grounds

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Beach

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (416)
"Cozy home overlooking the ocean. We loved sitting by the warm gas fireplace and looking at the scenic ocean view. Quiet and private. A very special place that I hope to return to!"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (361)
"The views from this house are insane!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
Valley of the Moon Getaway
Outdoor dining

Valley of the Moon Getaway

10.0 out of 10, Exceptional, (223)
"The property and location were beautiful! The pictures of the outside and landscape were not fake! The pictures of the inside of the home did not do it justice. Very clean and had everything you could need. Host was readily available to assist and answer any questions we could have"
Valley of the Moon Getaway
Panoramic Ocean View--3 Min Walk To Beach
Dining

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (291)
"What a great property. Rainy, windy weather, cozy house with everything we needed. Can’t wait to return. "
Panoramic Ocean View--3 Min Walk To Beach
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Interior

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

9.2 out of 10, Wonderful, (188)
"We really enjoyed the cozy spaciousness of this clean home, with multiple rooms to choose from, ample space to relax and a super functional kitchen. The host was very considerate of our needs, and left us welcome goodies on the counter which was an unexpected treat. We enjoyed the fireplace and wood was even provided. Could not have asked for more for a memorable weekend getaway!"
The price is AU$1,295
includes taxes & fees
24 Feb - 25 Feb
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
TV, fireplace, DVD player, books

Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

10.0 out of 10, Exceptional, (246)
"Cherry's house is so comfy and welcoming, and has such a great view of the ocean. We didn't even mind that the weather wasn't so great, we were more than happy to spend lots of time in the house. Lovely artwork everywhere you look, comfy beds, lots of kitchen equipment, the best location. PLUS handmade chocolates to welcome you! We had a lovely time and really look forward to staying here again. "
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Fridge, microwave, oven, stovetop

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Beach

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

9.6 out of 10, Exceptional, (162)
"Excellent location to be near bodega bay restaurants and The headlands -very nice and approachable host, very dog friendly place. "
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Double Queen Room Non-vaulted with Ocean View!
1 bedroom

Double Queen Room Non-vaulted with Ocean View!

9.0 out of 10, Wonderful, (4)
"Very nice modern room. Loved the fireplace and the view of the bay. Close to Bodega Bay restaurants and marina. "
The price is AU$415
includes taxes & fees
2 Mar - 3 Mar
Double Queen Room Non-vaulted with Ocean View!
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
Outdoor spa tub

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

10.0 out of 10, Exceptional, (67)
"We thoroughly enjoyed our second stay at this property. The River is gorgeous, the house is clean, all amenities readily available, close to hiking, beach, wine tasting. Quiet and serene area, neighborhood is great. Property management team was fantastic and helpful. Easy check in and out. One of my favorite VRBOs. "
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
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, (78)
"This is a lovely property with a great location! Great communication with property manager. Would definitely stay again!"
Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country
Calistoga Vineyard House
Smart TV, fireplace, stereo

Calistoga Vineyard House

10.0 out of 10, Exceptional, (34)
"Nice new place with great kitchen."
Calistoga Vineyard House
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, (222)
"This is a beautiful home in a quaint location to build special memories. We will definitely return!!"
The price is AU$3,252
includes taxes & fees
3 Mar - 4 Mar
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!
Miscellaneous

Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

9.8 out of 10, Exceptional, (159)
"Every year my husband and I plan a long weekend for our grown kids and their signficant others. Our favorite location is Bodega Bay and this is our favorite house! The views are amazing, the layout of the house is perfect for three couples and it is always clean and ready for us! We can't wait to come back!"
The price is AU$1,900
includes taxes & fees
3 Mar - 4 Mar
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!
The Tiny Tipsy Turtle
Outdoor dining

The Tiny Tipsy Turtle

2.0 star property
10.0 out of 10, Exceptional, (11)
"This was a comfortable and small perch in Guerneville. Very clean and perfectly adequate for our stay. We'd come again if we are in the area."
The price is AU$334
includes taxes & fees
23 Feb - 24 Feb
The Tiny Tipsy Turtle
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (219)
"Lavender Hill was the perfect spot for a weekend reunion with a bunch of friends to celebrate a milestone birthday! The home is beautiful and has everything you need for a great stay. The panoramic views were breathtaking and our group spent the majority of our stay in the living area soaking up the beauty. We had grand plans for making more use of the sport court and would've loved to use the pool (it was too cold), but this just makes it easier to plan a return stay in the future. Thanks to...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Wine Country Harvest Vacation Home
Outdoor dining

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (69)
"Very private large house and yard perfect!"
Wine Country Harvest Vacation Home
Vineyard and garden views, large open kitchen Space for play and meditaion
Terrace/patio

Vineyard and garden views, large open kitchen Space for play and meditaion

10.0 out of 10, Exceptional, (84)
"My family of four (two teenagers) and my brother and sister-in-law hand a wonderful stay over New Years Eve and Day. The location was convenient, quiet, with great views. We loved the modern kitchen, extremely well equipped, enjoyed the garden, and made for an amazing place to enjoy the wine country and just being lazy and enjoying the surrounding hills and scenery. Home has a great modern design with upscale finishes. "
Vineyard and garden views, large open kitchen Space for play and meditaion
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
Outdoor spa tub

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

8.4 out of 10, Very good, (22)
"The place and weather was perfect. The house was clean, organized and had plenty of towels. I love the jacuzzi. The neighbors were really nice. I am a computer person and the wifi was off and on but ita ok, its good to have some nature time also. "
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Windsor you may be interested in

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Courtyard

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Very clean"
The price is AU$208
includes taxes & fees
7 Mar - 8 Mar
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Holiday Inn Windsor Wine Country by IHG
Exterior

Holiday Inn Windsor Wine Country by IHG

3.0 star property
9.0 out of 10, Wonderful, (864)
"Great place to stay when visiting family "
The price is AU$166
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Windsor Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country
Exterior

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (999)
"Perfect location. Hot tub is a good size. Room was comfortable and plenty big for 4 people "
The price is AU$235
includes taxes & fees
27 Feb - 28 Feb
Hampton Inn & Suites Windsor - Sonoma Wine Country
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.

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 46 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 Sonoma-Cutrer Vineyards Cutrer Vineyard 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.