A stone bridge over a calm river, a historic tower, and illuminated buildings at dusk.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Windsor vacation rentals

Outdoor pool, a heated pool

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 ￥32,348
￥61,118 total
includes taxes & fees
Jul 27 - Jul 28
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
A heated pool

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, (46 reviews)
"Nice location to base from when visiting multiple wineries in the area. Fit our needs well with 2 bedrooms plus the murphy bed. Pool and hot tub were nice as well. I don't need the long sell on attending a hotel club event and having to pay for wifi if you wanted it doesn't seem right in 2026."
United States
Matthew G.
The price is ￥32,348
￥61,118 total
includes taxes & fees
Jul 28 - Jul 29
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor pool, a heated pool

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
10.0 out of 10, Exceptional, (1 review)
The price is ￥32,348
￥60,795 total
includes taxes & fees
Jul 23 - Jul 24
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Outdoor pool, a heated pool

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 ￥32,348
￥61,118 total
includes taxes & fees
Jul 28 - Jul 29
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Exterior

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.6 out of 10, Exceptional, (4 reviews)
"Nice camping spot "
United States
Evelyn
The price is ￥12,810
￥14,603 total
includes taxes & fees
Jun 28 - Jun 29
The Ranch at Lake Sonoma
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (28 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is ￥10,335
￥27,382 total
includes taxes & fees
Jun 30 - Jul 1
Cobb Mountain Chalet King Size Suite
Outdoor pool

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 ￥18,079
￥42,985 total
includes taxes & fees
Jul 20 - Jul 21
2 Hidden Wine Country Gem Upstairs Unit
TV

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is ￥16,178
￥32,841 total
includes taxes & fees
Jul 14 - Jul 15
Emerald Lodge quiet efficiency
Outdoor dining

Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and location!"
United States
Brandi K.
The price is ￥24,455
￥56,761 total
includes taxes & fees
Jun 28 - Jun 29
Peaceful, charming, cottage in wine country. Beautiful yard!
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (114 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is ￥23,516
￥26,809 total
includes taxes & fees
Jul 27 - Jul 28
Wildhaven Sonoma Glamping
Interior

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Lovely spot for a weekend in Russian River"
United States
Emily F.
The price is ￥24,495
￥70,682 total
includes taxes & fees
Jun 29 - Jun 30
2BR Bungalow | Russian River & Wine Country
Room, 1 Bedroom | Living area | Smart TV

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"Quaint mountain cabin, relaxing, clean, pet friendly, easy check in"
United States
Bethany
The price is ￥23,312
￥46,156 total
includes taxes & fees
Jun 28 - Jun 29
Rouge Cobb Mountain Hotel - Cabin 1
Terrace/patio

Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (34 reviews)
"Very nice, extremely well equpped home. Very quiet with great nlback patio. Would defistay here again."
United States
Bill F.
The price is ￥42,699
￥98,512 total
includes taxes & fees
Jul 7 - Jul 8
Somms Rest ⎮ Designed. Curated. Peaceful.
Terrace/patio

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Healdsburg
10.0 out of 10, Exceptional, (14 reviews)
"Great location!"
United States
Riley F.
The price is ￥27,664
￥65,423 total
includes taxes & fees
Jun 30 - Jul 1
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Exterior

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
8.6 out of 10, Excellent, (4 reviews)
"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.
The price is ￥28,878
￥49,816 total
includes taxes & fees
Jul 13 - Jul 14
Sebastopol Lux Walk toTown Guest Suite
Game room

Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (22 reviews)
"The location was perfect if you enjoy the Russian River Wineries and the Healdsburg area. The house itself is full of charm and character. It was nice to be able to unwind with friends at the dining table and play cards after a collaboratively cooked meal. The little town of Graton has a couple of good little restaurants, too!"
United States
Jeff D.
The price is ￥27,077
￥86,644 total
includes taxes & fees
Jun 30 - Jul 1
Relaxing Vineyard View, Rooftop Deck & Game Room
Dining

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (11 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is ￥32,348
￥80,870 total
includes taxes & fees
Jun 29 - Jun 30
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
2 bedrooms, desk, iron/ironing board, free WiFi

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (77 reviews)
"Overall a good place to stay in downtown Santa Rosa. "
United States
Stan R.
The price is ￥33,480
￥69,684 total
includes taxes & fees
Jul 1 - Jul 2
Wine Country Cottage in downtown Santa Rosa, CA
Beach

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (59 reviews)
"Really great place. Highly recommend!!!"
United States
Jennifer
The price is ￥27,826
￥47,020 total
includes taxes & fees
Jul 8 - Jul 9
The Tiny Tipsy Turtle
Beach

Modern House w. Fast Internet in 1 Acre Land

Modern House w. Fast Internet in 1 Acre Land
Occidental
8.6 out of 10, Excellent, (21 reviews)
"We loved this location, with hiking trails just around the corner, the ocean 15 minutes away, and very comfortable accommodation. "
United States
Sabrina R.
The price is ￥38,560
￥76,315 total
includes taxes & fees
Jun 29 - Jun 30
Modern House w. Fast Internet in 1 Acre Land
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

Calistoga Motor Lodge and Spa

Calistoga Motor Lodge and Spa

10/10 Excellent
"Location is great, staff very friendly."
Cecilia 3-night trip
Posted 2 hours ago
Calistoga Motor Lodge and Spa

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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 wineries and top-notch restaurants. 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?

Bird Watcher Paradise 2 Bedroom 2 Bath with Beautiful View: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 31 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. Pacific Coast Air Museum and Windsor Golf Club 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.