Book Holiday Homes in Windsor

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Windsor

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

Bodega Bay
When you a stay at this vacation home in Bodega Bay, you'll be on the waterfront, within a 5-minute walk of Bodega Harbour and Sonoma Coast State Park.
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

Bodega Bay
With a stay at this vacation home in Bodega Bay, you'll be on the beach, within a 10-minute drive of Russian River and Sonoma Coast State Park.
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Dillon Beach
Located in Dillon Beach, this vacation home is by the ocean, a 1-minute drive from Dillon Beach and 9 minutes from Tomales City Park.
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine
Save an average of 15% on thousands of hotels when you're signed in
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Healdsburg
With a stay at this vacation home in Healdsburg, you'll be within a 10-minute drive of Russian River and Pezzi King Winery.
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

Bodega Bay
When you stay at this vacation home in Bodega Bay, you'll be on the beach, within a 10-minute walk of Bodega Harbour Golf Links and Links at Bodega Harbour.
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Bodega Bay
Located in Bodega Bay, this vacation home is by the ocean, within a 5-minute drive of Bodega Harbour Golf Links and Links at Bodega Harbour.
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

Guerneville
When you stay at this vacation home in Guerneville, you'll be on the waterfront, just steps from Russian River and a 2-minute drive from Pee Wee Golf and ...
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #2 King Beds

Glen Ellen
The price is AU$683 per night from 17 Mar to 18 Mar
AU$683
includes taxes & fees
17 Mar - 18 Mar
With a stay at this vacation home in Glen Ellen, you'll be a 4-minute walk from Sonoma Valley Regional Park and within a 5-minute drive of Jack London ...
Glen Ellen Retreat #2 King Beds
Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley

Santa Rosa
With a stay at this vacation home in Santa Rosa (Northwest Santa Rosa), you'll be a 4-minute drive from Kendall-Jackson Wine Estate and Gardens and 5 minutes ...
Winemaker's Delight: 3BD/3BA Russian River Valley
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windsor Holiday Homes essential information

Accommodation
930 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$683
Popular accommodation
COZY Bungalow--Dog-Friendly—Perfect for Couples!!! , Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!, Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine, Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi, 4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave', ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH, ~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~, Glen Ellen Retreat #2 King Beds, Winemaker's Delight: 3BD/3BA Russian River Valley

Top trending hotels in Windsor

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is AU$194 per night from 23 Mar to 24 Mar
AU$194
includes taxes & fees
23 Mar - 24 Mar
Located in Windsor, Holiday Inn Windsor Wine Country by IHG is within a 10-minute drive of Kendall-Jackson Wine Estate and Gardens and Kendall-Jackson ...
Holiday Inn Windsor Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 out of 5
8865 Conde Lane, Windsor, CA
Fully refundable
The price is AU$252 per night from 17 Mar to 18 Mar
AU$252
includes taxes & fees
17 Mar - 18 Mar
A stay at Holiday Inn Express® Windsor Sonoma Wine Country by IHG places you in the heart of Windsor, within a 15-minute walk of Powell's Sweet Shoppe - Windsor ...
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 out of 5
8937 Brooks Road South, Windsor, CA
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 23 Mar to 24 Mar
AU$238
includes taxes & fees
23 Mar - 24 Mar
When you stay at Hampton Inn & Suites Windsor - Sonoma Wine Country in Windsor, you'll be in a regional park, within a 5-minute drive of Powell's Sweet Shoppe ...
Hampton Inn & Suites Windsor - Sonoma Wine Country
Save an average of 15% on thousands of hotels when you're signed in
The Sandman, Ascend Hotel Collection

The Sandman, Ascend Hotel Collection

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 30 Mar to 31 Mar
AU$140
includes taxes & fees
30 Mar - 31 Mar
With a stay at The Sandman, Ascend Hotel Collection in Santa Rosa, you'll be near the airport, within a 10-minute drive of Graton Resort and Casino and Empire ...
The Sandman, Ascend Hotel Collection
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.