Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
The price is €829
includes taxes & fees
14 May - 15 May
Windsor Home with Sauna & Outdoor Fire Pit

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 €316
includes taxes & fees
12 May - 13 May
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

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 €316
includes taxes & fees
12 May - 13 May
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

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 €316
includes taxes & fees
12 May - 13 May
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

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 €316
includes taxes & fees
12 May - 13 May
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

Two Separate 2BR Condos w/Pool & Hot Tub

Two Separate 2BR Condos w/Pool & Hot Tub
Windsor
The price is €4,091
includes taxes & fees
23 May - 24 May
Two Separate 2BR Condos w/Pool & Hot Tub

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is €297
includes taxes & fees
12 May - 13 May
Tranquil Redwood Retreat

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (13 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 €285
includes taxes & fees
12 May - 13 May
Enchanting Retreat in the heart of Redwoods

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (20 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is €297
includes taxes & fees
18 May - 19 May
Creekside Under the Redwoods

Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For
Cobb
9.6 out of 10, Exceptional, (18 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is €164
includes taxes & fees
17 May - 18 May
Cobb Mountain Chalet Main For

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 €311
includes taxes & fees
12 May - 13 May
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills

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 €231
includes taxes & fees
17 May - 18 May
2 Hidden Wine Country Gem Upstairs Unit

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 €207
includes taxes & fees
12 May - 13 May
Rouge Cobb Mountain Hotel - Cabin 3

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 €302
includes taxes & fees
19 May - 20 May
Peaceful, charming, cottage in wine country. Beautiful yard!

Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
10.0 out of 10, Exceptional, (32 reviews)
"Very nice, extremely well equpped home. Very quiet with great nlback patio. Would defistay here again."
United States
Bill F.
The price is €408
includes taxes & fees
14 May - 15 May
Somms Rest ⎮ Designed. Curated. Peaceful.

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (21 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is €432
includes taxes & fees
15 May - 16 May
Bright and modern - Water views - Close to beach

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
8.6 out of 10, Excellent, (4 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 €216
includes taxes & fees
12 May - 13 May
Sebastopol Lux Walk toTown Guest Suite

Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (37 reviews)
"Clean and comfortable place to stay, easy-check in, good amenities and location. Would definitely stay again."
United States
Scott W.
The price is €455
includes taxes & fees
12 May - 13 May
Serenity at the Russian River

Ocean & Golf Fairway view

Ocean & Golf Fairway view
Bodega Bay
8.6 out of 10, Excellent, (32 reviews)
"Gorgeous home with stunning view! Perfect for couple or a few friends. "
United States
Christine T.
Ocean & Golf Fairway view

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 €348
includes taxes & fees
12 May - 13 May
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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 €77 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?

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.