Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Windsor Vacation
Uncover the best parts of Windsor with a customized Windsor vacation package. From its lively atmosphere and cultural experiences to its spectacular views, you'll love experiencing this picturesque city the way you want to. Like to start exploring your surroundings? Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Windsor Oaks Vineyards are three of the top places to visit during a trip to Windsor. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windsor now.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort
Stonehouse
Price was CA $1,660, price is now CA $1,212 per person
CA $1,212
per person
Jul 24 - Jul 27
found 1 hour ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,377 reviews)
Nice enough for a short stay. 20 min walk to downtown. Bed was a little squeaky and not the most comfortable but it was clean and easy
Reviewed on May 17, 2026
the cottages of napa valley
Price was CA $2,311, price is now CA $1,595 per person
CA $1,595
per person
Jul 24 - Jul 27
found 1 hour ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
10/10 Exceptional! (19 reviews)
Beautiful cottage and amenities. LOVED the morning delivery of baked goods, and the jacuzzi tub. Truly the best romantic getaway in Napa.
Reviewed on Apr 12, 2026
Hotel Yountville
Price was CA $2,770, price is now CA $1,977 per person
CA $1,977
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.6/10 Exceptional! (1,002 reviews)
The room was lovely and recently upgraded, but the rest of the property, especially for the price, operates as a top notch motel. The front desk staff and check in assistance is less than helpful, there is no electric car charger, something almost mandatory these days at a hotel of this price. The restaurant operated on limited hours, no room service after 9, and I was looked on dumbfounded when I asked for breakfast on a Sunday at 11am! Overall, the feel is of a nice drive up motel and not a 5 star property in Yountville, but the price is the opposite.
I should say the cleaning staff was efficient and good, and the property was well maintained.
Reviewed on May 26, 2026
Lavender, A Four Sisters Inn
Price was CA $3,313, price is now CA $2,441 per person
CA $2,441
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.8/10 Excellent! (446 reviews)
Cozy and lovely. All the details of a perfect stay were thought of by the staff… it was absolutely wonderful.
Reviewed on May 19, 2026
Windsor Hotel Deals
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $180 per night from Jun 4 to Jun 5
CA $180
CA $205 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (1,062 reviews)
"Overall it was ok but the air conditioning was very noisy so I turned it off to sleep. The room had a stuffy smell which wasn’t pleasant!"
Reviewed on May 26, 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
The price is CA $191 per night from Jun 14 to Jun 15
CA $191
CA $219 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Room was clean. Location was close to shopping and gas. Easy highway access. Nice town."
Reviewed on May 25, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
The price is CA $180 per night from Jun 9 to Jun 10
CA $180
CA $205 total
Jun 9 - Jun 10
includes taxes & fees
9.2/10 Wonderful! (1,359 reviews)
"Bathroom didnt feel clean or properly maintained"
Reviewed on May 27, 2026
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.
Discover the most popular places to visit in Windsor
Windsor Oaks Vineyards
You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area, or check out its wineries.
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $68
per adult
86% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
CA $190
per adult
96% of travellers recommend
Explore a world of travel with Expedia
- Flights to Sonoma County
- Alaska Airlines Vancouver (YVR) to Santa Rosa (STS) flights
- Flights from San Rafael (AFA) to Santa Rosa (STS)
- Flights from Albany (ALB) to Santa Rosa (STS)
- Flights from Napa (APC) to Santa Rosa (STS)
- Flights from Appleton (ATW) to Santa Rosa (STS)
- Flights from Bucaramanga (BGA) to Santa Rosa (STS)
- Flights from Bangor (BGR) to Santa Rosa (STS)
- Flights from Bellingham (BLI) to Santa Rosa (STS)
- Flights from Buffalo (BUF) to Santa Rosa (STS)
- Flights from Clarksville (CKV) to Santa Rosa (STS)
- Flights from Cheyenne (CYS) to Santa Rosa (STS)
- Flights from Detroit (DTW) to Santa Rosa (STS)
- Flights from Fargo (FAR) to Santa Rosa (STS)
- Flights from Kalispell (FCA) to Santa Rosa (STS)
- Flights from Fort Lauderdale (FLL) to Santa Rosa (STS)
- Flights from Guadalajara (GDL) to Santa Rosa (STS)
- Flights from Spokane (GEG) to Santa Rosa (STS)
- Flights from Grand Island (GRI) to Santa Rosa (STS)
- Flights from Grand Rapids (GRR) to Santa Rosa (STS)
- Flights from Hagerstown (HGR) to Santa Rosa (STS)
- Flights from Lake Havasu City (HII) to Santa Rosa (STS)
- Flights from Harlingen (HRL) to Santa Rosa (STS)
- Flights from Jackson Hole (JAC) to Santa Rosa (STS)
- Flights from Joplin (JLN) to Santa Rosa (STS)
- Flights from Lansing (LAN) to Santa Rosa (STS)
- Flights from Los Angeles (LAX) to Santa Rosa (STS)
- Flights from Liberia (LIR) to Santa Rosa (STS)
- Flights from Lancaster (LNS) to Santa Rosa (STS)
- Flights from Morelia (MLM) to Santa Rosa (STS)
- Flights from Moorea (MOZ) to Santa Rosa (STS)
- Flights from Seattle Paine Field Intl. Airport (PAE) to Santa Rosa (STS)
- Flights from Portland (PDX) to Santa Rosa (STS)
- Flights from Phoenix (PHX) to Santa Rosa (STS)
- Flights from Palm Springs (PSP) to Santa Rosa (STS)
- Flights from Murrieta (RBK) to Santa Rosa (STS)
- Flights from Redding (RDD) to Santa Rosa (STS)
- Flights from Roswell (ROW) to Santa Rosa (STS)
- Flights from Scottsdale (SCF) to Santa Rosa (STS)
- Flights from Seattle (SEA) to Santa Rosa (STS)
- Flights from Sanford (SFM) to Santa Rosa (STS)
- Flights from San Francisco (SFO) to Santa Rosa (STS)
- Flights from Salt Lake City (SLC) to Santa Rosa (STS)
- Flights from Orange County (SNA) to Santa Rosa (STS)
- Flights from San Carlos (SQL) to Santa Rosa (STS)
- Flights from Syracuse (SYR) to Santa Rosa (STS)
- Flights from Texarkana (TXK) to Santa Rosa (STS)
- Flights from Vigo (VGO) to Santa Rosa (STS)
- Flights from Nanaimo (YCD) to Santa Rosa (STS)
- Flights from Edmonton (YEG) to Santa Rosa (STS)
- Flights from Halifax (YHZ) to Santa Rosa (STS)
- Flights from Kelowna (YLW) to Santa Rosa (STS)
- Flights from Ottawa (YOW) to Santa Rosa (STS)
- Flights from Comox (YQQ) to Santa Rosa (STS)
- Flights from Toronto (YTO) to Santa Rosa (STS)
- Flights from Montreal (YUL) to Santa Rosa (STS)
- Flights from Vancouver (YVR) to Santa Rosa (STS)
- Flights from Winnipeg (YWG) to Santa Rosa (STS)
- Flights from Saskatoon (YXE) to Santa Rosa (STS)
- Flights from Prince George (YXS) to Santa Rosa (STS)
- Flights from Abbotsford (YXX) to Santa Rosa (STS)
- Flights from Calgary (YYC) to Santa Rosa (STS)
- Flights from Penticton (YYF) to Santa Rosa (STS)
- Flights from Victoria (YYJ) to Santa Rosa (STS)
- Flights from Toronto (YYZ) to Santa Rosa (STS)
- Armstrong Redwoods State Park
- Beaver Creek Vineyards
- Bennett Valley Vacations
- Bohemian Grove
- Calistoga Hot Springs
- Calistoga Vacations
- Castello di Amorosa
- Charles Krug Winery
- Chateau Montelena Winery
- Chateau St. Jean Winery
- Dry Creek Vineyard
- Francis Ford Coppola Winery
- Jenner Vacations
- Johnson's Beach
- Ledson Winery and Vineyards
- Mazzocco Winery
- Middletown Vacations
- Occidental Vacations
- Old Faithful Geyser of California
- Osmosis Day Spa Sanctuary
- River Rock Casino
- Robert Louis Stevenson Museum
- Santa Rosa Vacations
- Sharpsteen Museum
- Soda Rock Winery
- Sonoma Coast State Park
- Sonoma County Vacations
- Spring Lake Park
- Villa Grande Vacations
- Windsor Oaks Vineyards
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
