Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
The price is CA $166
CA $1,053 total
includes taxes & fees
Mar 25 - Mar 26
Windsor Home with Sauna & Outdoor Fire Pit

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 CA $274
CA $516 total
includes taxes & fees
Apr 8 - Apr 9
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)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is CA $649
CA $1,448 total
includes taxes & fees
Mar 29 - Mar 30
Elegant Vineyard Living at a Private Wine Country Estate

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 CA $343
CA $602 total
includes taxes & fees
Apr 8 - Apr 9
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

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
The price is CA $343
CA $602 total
includes taxes & fees
Apr 8 - Apr 9
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 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 CA $343
CA $602 total
includes taxes & fees
Apr 8 - Apr 9
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (18 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is CA $208
CA $443 total
includes taxes & fees
Mar 25 - Mar 26
Creekside Under the Redwoods

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 CA $208
CA $445 total
includes taxes & fees
Mar 30 - Mar 31
Tranquil Redwood Retreat

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (25 reviews)
"Wonderful spot! Clean, quiet, great, shower and lovely deck. "
United States
Chloe K.
The price is CA $78
CA $206 total
includes taxes & fees
Mar 30 - Mar 31
Cobb Mountain Chalet King Size Suite

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 CA $287
CA $320 total
includes taxes & fees
Apr 10 - Apr 11
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, (19 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is CA $225
CA $639 total
includes taxes & fees
Mar 31 - Apr 1
Bright and modern - Water views - Close to beach

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is CA $235
CA $592 total
includes taxes & fees
Mar 25 - Mar 26
Russian River Retreat! Woodsy Guerneville Bungalow

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (5 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is CA $162
CA $540 total
includes taxes & fees
Apr 8 - Apr 9
2BR Bungalow | Russian River & Wine Country

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 CA $184
CA $400 total
includes taxes & fees
Mar 29 - Mar 30
2 Hidden Wine Country Gem Upstairs Unit

Luxury Sonoma Wine Country Retreat Near Healdsburg • Fire Pit • 2-for-1 Tastings

Luxury Sonoma Wine Country Retreat Near Healdsburg • Fire Pit • 2-for-1 Tastings
Healdsburg
10.0 out of 10, Exceptional, (9 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is CA $283
CA $599 total
includes taxes & fees
Mar 31 - Apr 1
Luxury Sonoma Wine Country Retreat Near Healdsburg • Fire Pit • 2-for-1 Tastings

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (71 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
The price is CA $261
CA $562 total
includes taxes & fees
Mar 25 - Mar 26
Wine Country Cottage in downtown Santa Rosa, CA

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
The price is CA $173
CA $357 total
includes taxes & fees
Mar 26 - Mar 27
Rouge Cobb Mountain Hotel - Cabin 1

Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #2 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (162 reviews)
"Absolutely loved our time at the Glen Ellen retreat. The home is so cozy and welcoming. "
United States
Amanda D.
The price is CA $343
CA $708 total
includes taxes & fees
Mar 25 - Mar 26
Glen Ellen Retreat #2 King Beds

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (50 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is CA $135
CA $266 total
includes taxes & fees
Mar 29 - Mar 30
The Tiny Tipsy Turtle

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, (84 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
The price is CA $343
CA $708 total
includes taxes & fees
Mar 25 - Mar 26
Glen Ellen Retreat #1 Hot Tub and King Beds
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Top Windsor Hotel Reviews

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers 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's the top vacation rental that Windsor has to offer?

Waterfront Home in Bodega Bay! 3Beds, 2Baths & panoramic ocean views.: Visitors like this Windsor vacation home rental. It is located on the beach and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

Choose from 26 Expedia vacation rentals in Windsor for a memorable vacation.

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 vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.