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.
Claremont Resort & Club
Claremont Hills
Price was CA $2,598, price is now CA $1,540 per person
CA $1,540
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Oakland (OAK)
9/10 Wonderful! (1,023 reviews)
Staff was not welcoming to hotel guests treated regulars much better.
Reviewed on Jul 8, 2026
Grand Reserve at The Meritage
Soscol Gateway South
Price was CA $6,015, price is now CA $4,507 per person
CA $4,507
per person
Sep 16 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
8.4/10 Very good! (611 reviews)
Our stay was only one night to attend a concert. We have never paid this much for a room. We believed we booked a room in the building where the concert was. However, we were not placed in that building. We were given a room at the very end of another building overlooking a construction staging area. The elevator did not work so we had to carry bags up the stairs. The food at the bar/pub area was pretty bad. The sauces were very watered down. The calamari was overcooked like rubber. Our stay in no way reflected the $700 paid. Do not recommend.
Reviewed on Jul 5, 2026
Milliken Creek Inn
Alta Heights
Price was CA $6,888, price is now CA $5,200 per person
CA $5,200
per person
Sep 16 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
9.2/10 Wonderful! (522 reviews)
Walked on the property and was amazed by the scenery. Top the views with friendly, welcoming and accommodating staff just made the stay amazing. Free breakfast was the icing on the cake. Ontime and surpassed our expectations for a "free meal." The views from the rooms were surreal. It's easy to pass while driving to the location, but once you're on the property, it's every part of a 5 star stay.
Reviewed on Jun 17, 2026
White House Napa
Napa Abajo
Price was CA $2,695, price is now CA $2,036 per person
CA $2,036
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
9.2/10 Wonderful! (630 reviews)
If you’re looking for an upmarket bed and breakfast this is a good spot
Reviewed on Jul 5, 2026
Windsor Hotel Deals
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 19 to Jul 20
CA $208
CA $238 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Nice and clean"
Reviewed on Jul 8, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
The price is CA $185 per night from Aug 2 to Aug 3
CA $185
CA $210 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (1,348 reviews)
"I received a $70 charge for a “stained towel” my son got some Gatorade on a towel. That in no way should be a charge let alone $70! Hoping they will make it right but when I talked to the people at the front desk no manager was on duty and couldn’t help me."
Reviewed on Jul 7, 2026
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $185 per night from Aug 2 to Aug 3
CA $185
CA $210 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,063 reviews)
"Nice"
Reviewed on Jul 6, 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.
Stay near popular Windsor attractions
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $71
per adult
86% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
CA $197
per adult
96% of travellers recommend
Frequently asked questions
Explore a world of travel with Expedia
- Flights from Toronto (YYZ) to Santa Rosa (STS)
- Flights from Liberia (LIR) to Santa Rosa (STS)
- Flights from Calgary (YYC) to Santa Rosa (STS)
- Flights from Vigo (VGO) to Santa Rosa (STS)
- Flights from Lake Havasu City (HII) to Santa Rosa (STS)
- Flights from Fort Lauderdale (FLL) to Santa Rosa (STS)
- Flights from Ottawa (YOW) to Santa Rosa (STS)
- Flights from Texarkana (TXK) to Santa Rosa (STS)
- Flights from Portland (PDX) to Santa Rosa (STS)
- Flights from Victoria (YYJ) to Santa Rosa (STS)
- Flights from Montreal (YUL) to Santa Rosa (STS)
- Flights from Buffalo (BUF) to Santa Rosa (STS)
- Flights from San Francisco (SFO) to Santa Rosa (STS)
- Flights from Hagerstown (HGR) to Santa Rosa (STS)
- Flights from Joplin (JLN) to Santa Rosa (STS)
- Flights from Moab (CNY) to Santa Rosa (STS)
- Flights from Vancouver (YVR) to Santa Rosa (STS)
- Flights from Halifax (YHZ) to Santa Rosa (STS)
- Flights from Seattle (SEA) to Santa Rosa (STS)
- Flights from Saskatoon (YXE) to Santa Rosa (STS)
- Flights from Jackson Hole (JAC) to Santa Rosa (STS)
- Flights from Bellingham (BLI) to Santa Rosa (STS)
- Flights from Grand Island (GRI) to Santa Rosa (STS)
- Flights from Spokane (GEG) to Santa Rosa (STS)
- Flights from Palm Springs (PSP) to Santa Rosa (STS)
- Flights from Fargo (FAR) to Santa Rosa (STS)
- Flights from Clarksville (CKV) to Santa Rosa (STS)
- Flights from Bangor (BGR) to Santa Rosa (STS)
- Flights from San Carlos (SQL) to Santa Rosa (STS)
- Flights from Toronto (YTO) to Santa Rosa (STS)
- Flights from Penticton (YYF) to Santa Rosa (STS)
- Flights from Orange County (SNA) to Santa Rosa (STS)
- Flights from Appleton (ATW) to Santa Rosa (STS)
- Flights from Prince George (YXS) to Santa Rosa (STS)
- Flights from Phoenix (PHX) to Santa Rosa (STS)
- Alaska Airlines Vancouver (YVR) to Santa Rosa (STS) flights
- Flights from Nanaimo (YCD) to Santa Rosa (STS)
- Flights from Seattle Paine Field Intl. Airport (PAE) to Santa Rosa (STS)
- Flights from Edmonton (YEG) to Santa Rosa (STS)
- Flights from Morelia (MLM) to Santa Rosa (STS)
- Flights from Abbotsford (YXX) to Santa Rosa (STS)
- Flights from Kalispell (FCA) to Santa Rosa (STS)
- Flights from Kelowna (YLW) to Santa Rosa (STS)
- Flights from Winnipeg (YWG) to Santa Rosa (STS)
- Flights from Comox (YQQ) to Santa Rosa (STS)
- Flights to San Francisco
- Flights to Healdsburg
- Flights from Reading (RDG) to Santa Rosa (STS)
- Flights from Rhinelander (RHI) to Santa Rosa (STS)
- Flights from Los Angeles (LAX) to Santa Rosa (STS)
- Flights from Detroit (DTW) to Santa Rosa (STS)
- Visit Windsor
- River Rock Casino
- Sonoma County Vacations
- Yountville Vacations
- San Francisco Vacations
- Sonoma Vacations
- Charles Krug Winery
- Armstrong Redwoods State Park
- Sharpsteen Museum
- Chateau Montelena Winery
- Sonoma Coast State Park
- Ledson Winery and Vineyards
- V. Sattui Winery
- Santa Rosa Vacations
- Occidental Vacations
- Napa Valley Balloons
- Osmosis Day Spa Sanctuary
- Golden Gate Bridge
- Windsor Oaks Vineyards
- Castello di Amorosa
- Robert Mondavi Winery
- St. Helena Vacations
- Doran Beach
- Dry Creek Vineyard
- Petaluma Vacations
- Alcatraz Island
- Calistoga Hot Springs
- Calistoga Vacations
- Bohemian Grove
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
