We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Windsor Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
30 rentals in Windsor.
Sort by:
Tripadvisor Sort
Spacious Cottage on Gorgeous Wine Country Estate, holiday rental in Windsor

Spacious Cottage on Gorgeous Wine Country Estate

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Russian River Valley Wine Country right outside of your door!, holiday rental in Windsor

Russian River Valley Wine Country right outside of your door!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful 4BR Home in the Heart of the Sonoma Wine Country, holiday rental in Windsor

Beautiful 4BR Home in the Heart of the Sonoma Wine Country

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Comfortable Home In The Heart Of The Wine Country., holiday rental in Windsor

Spacious Comfortable Home In The Heart Of The Wine Country.

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stunning home w/ pool, hot tub, decks, & gourmet kitchen - close to wineries!, holiday rental in Windsor

Stunning home w/ pool, hot tub, decks, & gourmet kitchen - close to wineries!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Sonoma Wine Nest - Location! Location! Location!, holiday rental in Windsor

Sonoma Wine Nest - Location! Location! Location!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor 2BR 2Bath Condo weekly/monthly nice resort Setting! Fire Housing, holiday rental in Windsor

Windsor 2BR 2Bath Condo weekly/monthly nice resort Setting! Fire Housing

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor Triathlon /Wine Country, holiday rental in Windsor

Windsor Triathlon /Wine Country

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Historic Queen Anne Victorian in the Heart of Windsor, holiday rental in Windsor

Historic Queen Anne Victorian in the Heart of Windsor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor - Wine Country/Triathlon, holiday rental in Windsor

Windsor - Wine Country/Triathlon

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Windsor rentals sent straight to your email!
Worldmark Wine Country Windsor/Healdsburg Resort Condo 2BR2Ba sleeps6, NICE!!, holiday rental in Windsor

Worldmark Wine Country Windsor/Healdsburg Resort Condo 2BR2Ba sleeps6, NICE!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor 2BR 2Bath Condo weekly/monthly nice resort Setting! Sleeps6, holiday rental in Windsor

Windsor 2BR 2Bath Condo weekly/monthly nice resort Setting! Sleeps6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Worldmark Windsor Wine Country 2BR/2Ba Last Minute Bookings, Short Stays!, holiday rental in Windsor

Worldmark Windsor Wine Country 2BR/2Ba Last Minute Bookings, Short Stays!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor home on Golf Course, holiday rental in Windsor

Windsor home on Golf Course

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Worldmark Windsor/Healdsburg Wine country resort Condos 3BEDROOM 2BATH Sleeps8, holiday rental in Windsor

Worldmark Windsor/Healdsburg Wine country resort Condos 3BEDROOM 2BATH Sleeps8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
COZY COUNTRY BARN: A world of peace and quiet with 200 wineries nearby, holiday rental in Windsor

COZY COUNTRY BARN: A world of peace and quiet with 200 wineries nearby

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Worldmark Windsor,  Wine Country 2BR 2Bath Sleeps6 Last Minute Availability!, holiday rental in Windsor

Worldmark Windsor, Wine Country 2BR 2Bath Sleeps6 Last Minute Availability!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
YOUR OWN FIVE STAR VACATION, holiday rental in Windsor

YOUR OWN FIVE STAR VACATION

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor/Healdsburg Wine country resort Condos 3BEDROOM!! 2BA Sleeps8 NICE!!, holiday rental in Windsor

Windsor/Healdsburg Wine country resort Condos 3BEDROOM!! 2BA Sleeps8 NICE!!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor, CA: Sonoma 1 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!, holiday rental in Windsor

Windsor, CA: Sonoma 1 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Windsor, CA: Sonoma 3 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!, holiday rental in Windsor

Windsor, CA: Sonoma 3 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Elegant Creek-Side Home with Large Deck, Fenced Yard & Private Hot Tub, holiday rental in Windsor

Elegant Creek-Side Home with Large Deck, Fenced Yard & Private Hot Tub

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Spacious Wine Country Getaway w/ Private Backyard, Updated Kitchen & AC, holiday rental in Windsor

Spacious Wine Country Getaway w/ Private Backyard, Updated Kitchen & AC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!, holiday rental in Windsor

Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Windsor, CA: Sonoma 2 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!, holiday rental in Windsor

Windsor, CA: Sonoma 2 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Corner-Lot Beauty | Gourmet Kitchen | Fenced Yard with Private Hot Tub, holiday rental in Windsor

Corner-Lot Beauty | Gourmet Kitchen | Fenced Yard with Private Hot Tub

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Superbowl 50; February 3-10, holiday rental in Windsor

Superbowl 50; February 3-10

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sonoma Wine Nest - Location! Location! Location!, holiday rental in Windsor

Sonoma Wine Nest - Location! Location! Location!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Windsor - Wine Country, holiday rental in Windsor

Windsor - Wine Country

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Relaxing comfortable 3 bedroom

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Windsor