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Holiday Rentals in Windsor

"Property was perfect for me while I was taking care of my grandchildren"

"Another wonderful stay! Huge storm! Amazed we didn’t lose power! Thank you for sharing your beautiful family home. "

"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!"

includes taxes & fees

9 Feb - 10 Feb

"A cozy magical little spot where you feel like all the beauty around is just for you. All the amenities made for a relaxing stay. We miss it already!"

"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...

"We had a lovely relaxing stay at Jujube, and hope to be back again soon. Thank you Bridgette!"

"We loved the home and the location. The property met or exceeded our expectations. In a side note, wish laundry detergent was available. Overall we would stay here again."

"We loved our 2-night stay. We especially loved that each person in our group had their own bedroom (and bathroom). The house is beautifully designed with comfortable beds and couches. The living/dining room has gorgeous massive ceilings. We also loved the huge dining table for meals/games, etc. The aesthetic throughout the house was right up the alley of our group. Everything you need is provided and has been thoughtfully curated. Every room was well-appointed and very clean.The hot tub...

"This property is simply amazing from the special touches and decorations that welcomed us for my daughter‘s bachelorette weekend to the recommendations of chef Misty Phelps all the touches were just simply above and beyond. We thoroughly enjoyed ourselves and had a wonderful time."

includes taxes & fees

12 Feb - 13 Feb

"Loved the property, right on the water, very clean, well stocked for cooking in. Highly recommend.My only complaint is the laundry list of check out items… we were only there for a short weekend and had to launder all towels before leaving with incredibly specific instructions about cycle length and amount of detergent, etc. our checkout was at 11am… it was a little stressful to get it all done. if we’re paying a few hundred for a cleaning service, shouldn’t that include laundering towels? Or...

"We loved our stay at "365 Days", especially the professional kitchen appliances and the back patio/view. The downstairs suite is separate from the upstairs living quarters, which provided some extra privacy for our large group. The house was clean and well stocked, we would love to stay again in the future. "

"Everything went great. The location is very convenient for hiking and restaurants. Everything is a short drivee away. Pamela was very helpful and allowed us to come in earlier than the check in time. She had wonderful suggestions for restaurants and hikes in the area. The bed was very comfortable and the location was very quiet. The kitchen had all that we needed including a nice supply of spices. We had excellent meals at the following:Fisheterian - Lunch - We had the fish tacos and...

"Our family getaway to Lavender Hill was definitely one to remember. This was for a joint birthday celebration for sister and mom, the perfect coming together place for our three families, ages ranging from 3yo to 80yo. We enjoyed our time making meals together in the spacious kitchen and countless hours spent outdoors - on the swings, court, around the fire pit, in the hot tub, and exploring the overall grounds. William was a fantastic host, so incredibly kind and thoughtful. Extremely...

"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"

"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "

"Don’t hesitate to book this place! Amazing 360 views, gorgeous house that’s even bigger and nicer than the photos. The owner Per is super nice and communicative. Everything in the house is top of the line. We loved it!"

"One of a kind property in a beautiful location. The layout was super well suited for our group, with lots of spaces to relax and enjoy each other's time. The host is great - very responsive and kind, with all the amenities you need/expect. Would love to stay at this property again. Thank you so much!"

includes taxes & fees

6 Mar - 7 Mar

"Expedia communication was horrible. Did not list address or lodging name. Room was great once we called for details."

includes taxes & fees

4 Mar - 5 Mar

"Great house with lots of amenities. Also had a pool table and a video game console. Good location with an excellent view of the sunset when not foggy. Our family had a great time and we would stay there again in the future."

"This was our second time in Bodega Bay. This location was great. My husband was able to fish and go and I was able to relax. The owner is nice. It was clean and had every thing you need. Also close to restaurants and stores. I do not want to stay no where else when we return. We were right on the water. "

includes taxes & fees

9 Feb - 10 Feb

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"The staff are excellent! I've been staying in the suites visiting family in the area and the hotel is amazing. Clean, well laid out. The only thing is a i wish they would give a map out to find our way. Lol. Sunken bath tub is so relaxing. Great location. I REALLY ENJOYED THE PRICE! Less than 180 is unheard of!"

includes taxes & fees

19 Feb - 20 Feb

"Everything was nice but the bathroom fan did not work"

includes taxes & fees

7 Mar - 8 Mar

"Perfect location. Hot tub is a good size. Room was comfortable and plenty big for 4 people "

includes taxes & fees

23 Feb - 24 Feb

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 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?

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.

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Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

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

Oceanfront - Hot Tub - Newly Remodeled Cottage

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

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

Seaside Modern - Easy 3 min Walk to Beach!

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

Luxury Napa Estate With Pool/Hot-tub/Concierge

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

365 Days Great Views of Dillon Beach

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

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

Valley of the Moon Getaway

1 Acre with 3 homes in the heart of wine country with last minute specials!

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms

King Non-vaulted Ceiling

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

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

Other types of properties in Windsor you may be interested in

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Hampton Inn & Suites Windsor - Sonoma Wine Country

Find out more about Windsor

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