Holiday rentals in Windsor

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Popular amenities for Windsor holiday rentals

Stay near Windsor's top sights

Luther Burbank Center for the Arts71 locals recommend
John Ash & Co.65 locals recommend
Kendall-Jackson Wine Estate & Gardens46 locals recommend
J Vineyards & Winery43 locals recommend
Marla Bakery & Catering38 locals recommend
Oliver's Market - Windsor37 locals recommend

Other great holiday rentals in Windsor

Top guest favourite
Home in Sebastopol
5 out of 5 average rating, 41 reviews

Pixel Place - A Private Arcade + Outdoor Sanctuary

JeffreyRating, 5 stars2 weeks ago
My family and I had such a great stay at Michael and Edna’s place! The house was easy to find and check in was smooth. We had an absolute blast in the game room! So many fun arcade games to keep the whole family having fun and entertained! I’m not sure if the kids or adults had more fun! The backyard was secluded and beautifully landscaped. The house is a short drive to downtown Sebastopol so it was super easy to explore. We would look for this place again if we’re ever back in the area. Thanks for a great stay!
Guest favourite
Home in Windsor
4.88 out of 5 average rating, 97 reviews

Escape to Paradise: Stunning Home in Wine Country

CarolynRating, 5 stars1 week ago
Johnathan’s place was great. Well Appointed kitchen. The master is really nice and a very big master bath too. The other bathroom for our guests was fine just no where near as nice as the master bath. Kitchen had everything you could possibly need. Great neighborhood. Felt very safe.
Superhost
Home in Healdsburg
4.81 out of 5 average rating, 145 reviews

Spectacular Vineyard View!! SPA, Close to Plaza!

ZakRating, 5 stars2 weeks ago
Loved our stay and would be happy to come back on our next trip
Guest favourite
Home in Bodega Bay
4.77 out of 5 average rating, 48 reviews

Beautiful South Harbor Home With Great Ocean Views

CoryRating, 5 stars7 months ago
Fantastic views of the local coast, Tomales Point and Pt. Reyes from the house. Easy access down to some quiet beaches via the trail across the street. The kitchen was the best equipped rental I've ever used, which was perfect since we were planning to cook up an epic seven course dinner! All around a great stay in beautiful Bodega Bay.
Guest favourite
Home in Bodega Bay
4.92 out of 5 average rating, 175 reviews

Bodega Bay-Magical Ocean Front and Coastal View!

GillianRating, 5 stars1 week ago
We thoroughly enjoyed our stay at Deja Blu. The location is perfection! Private, with beautiful gardens, only a hop, skip and a jump from the ocean. Falling asleep to the sound of crashing waves at night was divine. The home was clean and comfortable, and Barr was a lovely, helpful host. If you are looking to unwind in serenity, I highly recommend this home.
Guest favourite
Guest house in Middletown
4.86 out of 5 average rating, 163 reviews

Countryside Cottage

BethRating, 5 stars3 weeks ago
Nice and convenient to Harbin Hot springs. close to grocery and a few restaurants. Nice country area with great view of mountains and horses. Peaceful except for a bit of road noise, but it wasn't too bothersome. We would have appreciated some better quality bathroom towels, washcloths, more dishtowels etc. Jakob responded right away to questions about heater and lack of washcloths. He brought some wash cloths over with an hour. overall, very nice stay. Would recommend this place as good value.
Top guest favourite
Home in Sonoma
4.98 out of 5 average rating, 110 reviews

Sonoma 14Acres, 2BR 2BA, Pool HotTub, Plaza 3 mi.

AndreaRating, 5 stars3 weeks ago
Mike and Jefferson have created such a lovely sanctuary with this home. The beautifully landscaped garden area, outdoor living space, and fantastic amenities all made it feel like our very own private retreat. The property is quite expansive, with multiple areas for gathering, as well as several private spots for quietude. Whether swimming in the fantastic pool, relaxing in the hot tub, grilling dinner in the outdoor kitchen/dining area, or just gathering around the fire table, we looked forward to just being outside at home most of the time and didn't want to leave! Inside, however, was really just as cozy, with a well-stocked kitchen, including an espresso machine that made excellent cappuccinos that I looked forward to each day. This home is perfect for families -- our kids loved not just the pool but also all the other "toys" like the tire swing, table tennis, and basketball hoop. Would love to return and will recommend this property to others without any hesitation!
Guest favourite
Home in Dillon Beach
4.94 out of 5 average rating, 285 reviews

Classic Bungalow at Dillon Beach

AndiRating, 5 stars3 weeks ago
This home is a gem in the Dillon Beach area. It is updated, clean and comfortable. Less than 5 minutes walk to the beach or general store that has anything you might need (plus soft serve!). The general store is part of the Dillon Beach Resort which also has a great restaurant with stunning views of the beach.

Quick stats about holiday rentals in Windsor

  • Total rentals

    350 properties

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    260 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    260 properties have a pool

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Destinations to explore

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  2. United States
  3. California
  4. Sonoma County
  5. Windsor