Windsor Castle

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

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 AED 735
AED 1,388 total
includes taxes & fees
21 Jun - 22 Jun
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, (45 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is AED 735
AED 1,370 total
includes taxes & fees
24 Jun - 25 Jun
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 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 AED 735
AED 1,388 total
includes taxes & fees
21 Jun - 22 Jun
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 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 AED 735
AED 1,388 total
includes taxes & fees
21 Jun - 22 Jun
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Pool

Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.0 out of 10, Wonderful, (4 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
The price is AED 3,089
AED 6,014 total
includes taxes & fees
25 Jun - 26 Jun
Eastside Eden - Pool, Hot Tub and Tastings Included
Fridge, microwave, oven, stovetop

1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!

1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!
Downtown St. Helena
10.0 out of 10, Exceptional, (274 reviews)
"Great stay in a great location. The home was comfortable, had all the amenities for comfort, and was an easy walk into town. Scenic, quiet neighborhood. We would love to come back!"
United States
Margaret L.
The price is AED 4,408
AED 5,873 total
includes taxes & fees
23 Jun - 24 Jun
1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Downtown St. Helena
10.0 out of 10, Exceptional, (264 reviews)
"Amazing house, great location, hosts were very responsive. "
United States
Kevin C.
The price is AED 6,060
AED 7,803 total
includes taxes & fees
14 Jun - 15 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Towels

Downtown Cottage House

Downtown Cottage House
Downtown St. Helena
9.6 out of 10, Exceptional, (25 reviews)
"The location of the property is the best. "
United States
Kim B.
The price is AED 2,994
AED 4,541 total
includes taxes & fees
30 Jun - 1 Jul
Downtown Cottage House
Property grounds

Ambrose Bierce House

Ambrose Bierce House
Downtown St. Helena
9.8 out of 10, Exceptional, (29 reviews)
"The innkeepers were outstanding. The facility is wonderful - easy location to enjoy St. Helena and Napa Valley."
United States
Steve H.
Ambrose Bierce House
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 AED 404
AED 790 total
includes taxes & fees
30 Jun - 1 Jul
Emerald Lodge quiet efficiency
Porch

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 AED 768
AED 856 total
includes taxes & fees
3 Jul - 4 Jul
Backyard Garden Oasis
Exterior

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (40 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is AED 1,098
AED 1,506 total
includes taxes & fees
15 Jun - 16 Jun
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
The price is AED 988
AED 1,356 total
includes taxes & fees
15 Jun - 16 Jun
Escape to wine country in your independent cottage in downtown Calistoga
Outdoor dining

WineCountry Retreat + Casita,Bocce & Sunset Views!

WineCountry Retreat + Casita,Bocce & Sunset Views!
Glen Ellen
9.4 out of 10, Exceptional, (15 reviews)
"The owner was easy to talk to and checked in daily if we had any issues or help needed. "
United States
Christopher L.
The price is AED 970
AED 2,619 total
includes taxes & fees
28 Jun - 29 Jun
WineCountry Retreat + Casita,Bocce & Sunset Views!
Exterior

Luxury Napa Estate With Pool/Hot-tub/Concierge

Luxury Napa Estate With Pool/Hot-tub/Concierge
Calistoga
10.0 out of 10, Exceptional, (59 reviews)
"En suite rooms were perfect for group travel. The house was beautiful and comfortable. Hosts were very attentive and helpful. "
United States
Caylin E.
The price is AED 5,951
AED 9,566 total
includes taxes & fees
30 Jun - 1 Jul
Luxury Napa Estate With Pool/Hot-tub/Concierge
Dining

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is AED 657
AED 844 total
includes taxes & fees
22 Jun - 23 Jun
Comfort and Style in Our Queen Cottage
TV, fireplace, books

Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (33 reviews)
"This cozy place was exactly as pictured and spotless. Communication with the owners was easy and responsive. We really enjoyed our stay and would happily return."
United States
Summer S.
The price is AED 1,392
AED 1,799 total
includes taxes & fees
22 Jun - 23 Jun
Napa Valley Retreat in Calistoga!
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is AED 268
AED 659 total
includes taxes & fees
16 Jun - 17 Jun
Cobb Mountain Chalet King Size Suite
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 AED 462
AED 951 total
includes taxes & fees
15 Jun - 16 Jun
Rouge Cobb Mountain Hotel - Cabin 1
TV, fireplace, stereo

Sonoma Creek Haven - Creekside Hot Tub Retreat

Sonoma Creek Haven - Creekside Hot Tub Retreat
Kenwood
10.0 out of 10, Exceptional, (15 reviews)
"This place was amazing! Close to wineries, but private and felt like an escape! "
United States
Ellie R.
Sonoma Creek Haven - Creekside Hot Tub Retreat
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

WorldMark Windsor

WorldMark Windsor

10/10 Excellent
"Spacious accommodations, clean, friendly staff and full kitchen."
Marc 2-night trip
Posted 1 hour ago
WorldMark Windsor

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Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Powell's Sweet Shoppe - Windsor, 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 32 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Family-friendly attractions include Powell's Sweet Shoppe - Windsor and Dom Whitney Tasting Lounge, 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.