Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

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, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is €326
includes taxes & fees
10 Feb - 11 Feb
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"Stayed here for a wedding "
United States
Lanna E.
The price is €779
includes taxes & fees
10 Feb - 11 Feb
Elegant Vineyard Living at a Private Wine Country Estate

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
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 €270
includes taxes & fees
10 Mar - 11 Mar
Tranquil Redwood Retreat

Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #2 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (159 reviews)
"Excellent place to stay with 4 people. The place was quiet, clean and spacious and we loved the back yard! We would definitely stay here again when visiting Sonoma,"
United States
Pam S.
The price is €349
includes taxes & fees
10 Feb - 11 Feb
Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen
10.0 out of 10, Exceptional, (82 reviews)
"Very clean and excellent location."
United States
carrie k.
The price is €359
includes taxes & fees
10 Feb - 11 Feb
Glen Ellen Retreat #1 Hot Tub and King Beds

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 €242
includes taxes & fees
5 Mar - 6 Mar
2 Hidden Wine Country Gem Upstairs Unit

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is €395
includes taxes & fees
10 Feb - 11 Feb
Charming King Cottage

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Old Town Bodega Bay
9.4 out of 10, Exceptional, (355 reviews)
"Loved this property and the views. "
United States
anne
The price is €468
includes taxes & fees
10 Feb - 11 Feb
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (28 reviews)
"Very clean room, friendly staff, great to walk around "
United States
Victoria
The price is €152
includes taxes & fees
11 Mar - 12 Mar
Mandala Springs Wellness Retreat Center

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 €168
includes taxes & fees
10 Feb - 11 Feb
Backyard Garden Oasis

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (18 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is €395
includes taxes & fees
10 Feb - 11 Feb
Bright and modern - Water views - Close to beach

The Sonoma Spyglass | Incredible Views + Sauna

The Sonoma Spyglass | Incredible Views + Sauna
Sebastopol
10.0 out of 10, Exceptional, (5 reviews)
"This stay exceeded our expectations. Absolutely stunning and such a nice place for a staycation! 5 Stars across the board for everything. Will definitely book this place again in the future."
United States
Michael
The price is €525
includes taxes & fees
10 Feb - 11 Feb
The Sonoma Spyglass | Incredible Views + Sauna

“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino

“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino
Southwest Santa Rosa
10.0 out of 10, Exceptional, (6 reviews)
"Myself and four guests thoroughly enjoyed our overnight stay! The home had everything we needed and more - clean, cozy, and beautifully equipped with wonderful amenities. The beds were incredibly comfortable, and our host was very welcoming and attentive. We couldn’t have asked for a better experience. Highly recommend!"
United States
JoAnn P.
The price is €305
includes taxes & fees
10 Feb - 11 Feb
“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
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 €372
includes taxes & fees
10 Feb - 11 Feb
Comfort and Style in Our Queen Cottage

Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (30 reviews)
"This Smart home is very comfortable and well equipped. Beds are super comfy! Perfect for our girls weekend!"
United States
Mary K.
The price is €593
includes taxes & fees
10 Feb - 11 Feb
Wine Country Getaway

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (63 reviews)
"This cottage was so cute! So close to the beach, super comfortable beds, and Valerie was an awesome host! This is a must stay if you are looking for a place in Dillon beach "
United States
Lauren S.
The price is €483
includes taxes & fees
11 Feb - 12 Feb
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
Emerald Lodge quiet efficiency

Harbor Kee Peaceful Escape By The Bay

Harbor Kee Peaceful Escape By The Bay
Bodega Bay
9.6 out of 10, Exceptional, (24 reviews)
"We really enjoyed the historic home. Centrally located, close the restaurants "
United States
Pati K.
Harbor Kee Peaceful Escape By The Bay

Norcal Hideaway

Norcal Hideaway
Guerneville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful setting "
United States
LouAnn O.
The price is €419
includes taxes & fees
10 Feb - 11 Feb
Norcal Hideaway

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (65 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
The price is €344
includes taxes & fees
10 Feb - 11 Feb
Wine Country Cottage in downtown Santa Rosa, CA
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €152 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Bodega Bay on the Edge of Pacific Ocean: This holiday home rental outside of Windsor is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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.