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Windsor Vacation Rentals

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Nov 2 - Nov 3
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Nov 7 - Nov 9
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Nov 14 - Nov 16

Vacation Rentals in Windsor

Outdoor spa tub
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Luxury Estate Awaits: Your Ultimate Vineyard Escape
10.0 out of 10, Exceptional, (2)
"Beautiful home and property. Great location, close to so many vineyards and other places we wanted to visit. Cynthia was so great to work with! Would definitely stay here again. "
United States
Denise F.
$1,024 nightly
The price is $1,132
Nov 3 - Nov 4
Total with taxes and fees
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Exterior
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43)
"Great location near brewing restaurant, great amenities for kids. Place was bigger than expected and fit adults and kids comfortably. Easy parking and access.Only complaint was that the timeshare staff spent 15 mins with me after checkin trying to get me to signup for a time share meeting, when I was alone trying to watch my two young children who did not want to sit still. I didn’t realize it was a timeshare facility and that might be my fault. "
United States
Nicole D.
$506 nightly
The price is $560
Nov 24 - Nov 25
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Front of property
The Ranch at Lake Sonoma
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 !"
United States
Tamara
$79 nightly
The price is $90
Nov 3 - Nov 4
Total with taxes and fees
The Ranch at Lake Sonoma
Interior
Tranquil Redwood Retreat
Tranquil Redwood Retreat
8.8 out of 10, Excellent, (10)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
$307 nightly
The price is $340
Nov 3 - Nov 4
Total with taxes and fees
Tranquil Redwood Retreat
Meeting facility
Mandala Springs Wellness Retreat Center
Mandala Springs Wellness Retreat Center
3.5 star property
8.6 out of 10, Excellent, (27)
"Everything was great ... except the people staying next door in the cabin to me intruded in my space. This had nothing to do with the property though just rude bad manner people. The property folks were amazing about communicating. The site is very nice and the new cabins are terrific."
United States
Lisa
$244 nightly
The price is $272
Nov 3 - Nov 4
Total with taxes and fees
Mandala Springs Wellness Retreat Center
Property grounds
Backyard Garden Oasis
Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51)
"Greta was an amazing host, which made for a restful couple of days. Enjoyed the homemade goodies each morning"
United States
les
$194 nightly
The price is $216
Nov 3 - Nov 4
Total with taxes and fees
Backyard Garden Oasis
Property grounds
Sebastopol Lux Walk toTown Guest Suite
Sebastopol Lux Walk toTown Guest Suite
10.0 out of 10, Exceptional, (1)
"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.
$241 nightly
The price is $257
Nov 3 - Nov 4
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
Exterior detail
Cobb Mountain Chalet Main For
Cobb Mountain Chalet Main For
9.6 out of 10, Exceptional, (14)
"Just what we needed while visiting our family."
United States
Jason O.
$176 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
Cobb Mountain Chalet Main For
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
10.0 out of 10, Exceptional, (1)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
$488 nightly
The price is $549
Nov 3 - Nov 4
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Outdoor dining
The Tiny Tipsy Turtle
The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (37)
"Our stay at the Tipsy Turtle was wonderful. The property is right in the downtown area which makes it very easy to walk to dinners, or stroll around town.The property owner was incredible, and helped us with parking and check in.All in all a great stay! "
United States
Steve W.
$182 nightly
The price is $194
Nov 6 - Nov 7
Total with taxes and fees
The Tiny Tipsy Turtle
Beach
Wine Country Cottage in downtown Santa Rosa, CA
Wine Country Cottage in downtown Santa Rosa, CA
9.8 out of 10, Exceptional, (60)
"Wonderful and charming cottage! Great location ... shops and restaurants close by within casual walking distance. Super clean with every amenity we needed. Hosts were communicative and very responsive to questions upon our arrival. Thank you, Tim and Caroline!"
United States
Raymond L.
$363 nightly
The price is $384
Nov 3 - Nov 4
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Outdoor dining
Garden house with gas fireplace
Garden house with gas fireplace
10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
$203 nightly
The price is $223
Nov 3 - Nov 4
Total with taxes and fees
Garden house with gas fireplace
Terrace/patio
Escape to Wine County in your independant Cottage in Downtown Calistoga
Escape to Wine County in your independant Cottage in Downtown Calistoga
9.6 out of 10, Exceptional, (28)
"We were extremely pleased with the location and overall condition of the property! We will definitely look for this property the next time we are visiting Napa Valley!"
United States
Mike C.
$342 nightly
The price is $410
Nov 3 - Nov 4
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Outdoor dining
Lovely Russian River Bungalow-2BR 1 BA New Remodel
Lovely Russian River Bungalow-2BR 1 BA New Remodel
10.0 out of 10, Exceptional, (3)
"Darling small bungalow style home that was nicely decorated and comfortable. Bonus outdoor patio that we really enjoyed. Good location. Road to home had some twist and turns. Just be cautious and drive slowly. Definitely recommend! We loved our stay here."
United States
Kevin M.
$358 nightly
The price is $402
Nov 3 - Nov 4
Total with taxes and fees
Lovely Russian River Bungalow-2BR 1 BA New Remodel
Smart TV, books
Creekside Cozy 2BR 1BA + 2 Acres
Creekside Cozy 2BR 1BA + 2 Acres
2.0 star property
9.6 out of 10, Exceptional, (4)
"It was well set up. Enjoyed the stay very much. "
United States
Tabitha T.
$378 nightly
The price is $425
Nov 3 - Nov 4
Total with taxes and fees
Creekside Cozy 2BR 1BA + 2 Acres
Terrace/patio
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Escape to Wine Country in your independant Cottage in Downtown Calistoga
10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$342 nightly
The price is $410
Nov 3 - Nov 4
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Outdoor spa tub
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
9.8 out of 10, Exceptional, (7)
"The online description was accurate. Served as a nice base for exploring Sonoma County west of the 101. Very relaxed feel. Fun to see all of the farm animals on the surrounding properties."
United States
Kyle W.
$422 nightly
The price is $466
Nov 3 - Nov 4
Total with taxes and fees
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
Outdoor dining
Bright and modern - Water views - Close to beach
Bright and modern - Water views - Close to beach
10.0 out of 10, Exceptional, (16)
"Our stay at Kellie's Dillon Beach home was so very comfortable and had everything we needed. Super comfortable bed, awesome kitchen and loved the patios!"
United States
Nancy F.
$412 nightly
The price is $462
Nov 3 - Nov 4
Total with taxes and fees
Bright and modern - Water views - Close to beach
Room, 1 Bedroom | Property grounds
Rouge Cobb Mountain Hotel - Cabin 4
Rouge Cobb Mountain Hotel - Cabin 4
3.0 star property
$203 nightly
The price is $226
Nov 3 - Nov 4
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 4
Outdoor spa tub
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
2.0 star property
10.0 out of 10, Exceptional, (11)
"This home was absolutely stunning. Even better than the pictures! Can’t wait to come back."
United States
Merissa H.
$438 nightly
The price is $484
Nov 4 - Nov 5
Total with taxes and fees
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
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

The Inn at the Tides

The Inn at the Tides

10/10 Excellent
"Breakfast used to (years ago) include a proper meal (hot), but now is pretty basic. Times have changed, I know and it’s fine for what it is. Everything else was more than fantastic! Lovely king room, 2nd floor, with fireplace. Highly recommend!"
Sheryl 2-night trip
Posted 2 days ago
The Inn at the Tides

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Bodega Bay on the Edge of Pacific Ocean: Visitors like this Windsor vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Windsor?

Choose from 32 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 Windsor Oaks Vineyards 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.