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Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (342)
"We enjoyed our stay at this well equipped and designed cottage. We loved the decks and location on the river. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

7 Bedroom Oceanfront in Dillon Beach with spa

9.4 out of 10, Exceptional, (162)
"We have a group of four families that stay here once a year. It's always a pleasure, and every time we stay we see a few more things are improved from the last time we were there... which is always nice to see."
7 Bedroom Oceanfront in Dillon Beach with spa

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (393)
"This property is in a great location located on the ocean in bodega Bay. Great ocean views, gardens, very clean property 12 minutes from restaurants hiking trails everywhere. We had a wonderful stay."
Oceanfront - Hot Tub - Newly Remodeled Cottage

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (455)
"It was great as always"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is €57
includes taxes & fees
25 Sept - 26 Sept
The Ranch at Lake Sonoma

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

9.6 out of 10, Exceptional, (186)
"Perfect get away for my wifes 60th."
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

8.2 out of 10, Very good, (46)
"Walking distance to the beach and a warm and inviting space to return to. Perfect for our weekend getaway."
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

9.0 out of 10, Wonderful, (304)
"Ideal spot next to Dillon beach, which is dog friendly and close to so many other points of interest! We had a lovely time relaxing here and listening to the surf."
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway

9.0 out of 10, Wonderful, (94)
"Beautiful view, litterally on tge water."
Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway

Wine Country Getaway With Pool, Hot Tub, Garden, Views, Location!

9.8 out of 10, Exceptional, (132)
"We had an incredible stay at this lovely home in Glen Ellyn! The house easily and comfortably sleeps up to 12. Very clean with a beautiful kitchen. The grounds are incredible. The pool is delightful and so is the rock waterslide. We loved dining on the Tuscan inspired outdoor table each evening and listened to music around the pit fire afterward. The gardens are so pretty. Our host was just lovely to work with! We will be back next year."
Wine Country Getaway With Pool, Hot Tub, Garden, Views, Location!

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

10.0 out of 10, Exceptional, (242)
"Loved the house and location! "
The price is €2,077
includes taxes & fees
25 Sept - 26 Sept
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

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

9.4 out of 10, Exceptional, (346)
"The property was beautiful and perfect! We absolutely loved our stay here, and are looking forward to coming back again."
The price is €479
includes taxes & fees
29 Sept - 30 Sept
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (25)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is €353
includes taxes & fees
29 Sept - 30 Sept
Escape to Wine County in your independant Cottage in Downtown Calistoga

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (131)
"Cozy Location for a Corporate retreat!"
Casa Bella Estate in Wine Country w/ New Pool!

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

10.0 out of 10, Exceptional, (281)
"Lovely house, setting and host!"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs

9.8 out of 10, Exceptional, (97)
"Perfect yard for our tiny dogs. We even had 2 foxes visit up on the roof. Perfect location to walk to stores and quick drives to hikes."
Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs

Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach

10.0 out of 10, Exceptional, (21)
"The house was fantastic and in a great location. We'd definitely stay here again on future trips."
Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach

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

10.0 out of 10, Exceptional, (237)
"Truly one of the best rentals I’ve ever stayed in. The host is super responsive and easy to work with, the house is great and the views/outdoor space are absolutely incredible. Would love to return in the future! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

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

10.0 out of 10, Exceptional, (65)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (155)
"We had a great time hanging out at the pool with the family,"
Luxurious Large Home, Beautiful Pool, Extensive Gardens
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

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 €57 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 top-notch restaurants and wineries. 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?

7 Bedroom Oceanfront in Dillon Beach with spa: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 34 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.