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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Brannan Cottage Inn

Brannan Cottage Inn

3 out of 5
Save 100% on your flight
Price was $795, price is now $583 per person
$583
per person
Dec 7 - Dec 11
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
Stay at this inn in Calistoga. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Calistoga Hot Springs and Castello di Amorosa are located nearby.
Absolutely beautiful property! And perfect location. Wonderful staff, terrific amenities in each room. (M & M’s & Gummy Bears?!? Yes, please!). They even provide little packets of shaving cream! We will def be back!

Reviewed on Sep 21, 2026

Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Price was $858, price is now $603 per person
$603
per person
Dec 16 - Dec 19
found 22 hours ago
Roundtrip flight included
Denver (DEN) to Oakland (OAK)
Book a stay at this luxury hotel in Berkeley. Enjoy 3 outdoor pools, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Berkeley Marina and Jack London Square are located nearby.

Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

4 out of 5
Save 100% on your flight
Price was $1,318, price is now $933 per person
$933
per person
Dec 3 - Dec 7
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Oakland (OAK)
Book a stay at this spa resort in Sonoma. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Sonoma Plaza and Sonoma Golf Club are located nearby.

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $1,569, price is now $1,146 per person
$1,146
per person
Dec 3 - Dec 6
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
Book a stay at this luxury hotel in Calistoga. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Calistoga Hot Springs and Castello di Amorosa are located nearby.

North Block Hotel

North Block Hotel

4 out of 5
Save 100% on your flight
Price was $1,067, price is now $782 per person
$782
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Oakland (OAK)
Book a stay at this spa hotel in Yountville. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Maisonry Napa Valley and Yountville Park are located nearby.
Le site et la chambre sont très propre et l'accueil est très bien.

Reviewed on Sep 23, 2026

White House Napa - Adults Only

White House Napa - Adults Only

4 out of 5
Save 100% on your flight
Price was $1,403, price is now $1,038 per person
$1,038
per person
Dec 3 - Dec 7
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Oakland (OAK)
Book a stay at this boutique hotel in Napa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Napa Valley Wine Train and Uptown Theater are located nearby.

Meadowood Napa Valley

Meadowood Napa Valley

5 out of 5
Save 100% on your flight
Price was $2,127, price is now $1,592 per person
$1,592
per person
Dec 3 - Dec 6
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
Book a stay at this luxury hotel in St. Helena. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions V. Sattui Winery and Castello di Amorosa are located nearby.

R Inn Napa

R Inn Napa

3.5 out of 5
Price was $1,395, price is now $1,045 per person
$1,045
per person
Dec 3 - Dec 7
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Oakland (OAK)
Book a stay at this boutique hotel in Napa. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Napa Valley Wine Train and Uptown Theater are located nearby.
The best hotel I’ve ever stayed at. I don’t normally leave reviews but this place deserves one. I highly recommend. Thank you, R Inn. Our stay was excellent.

Reviewed on Sep 21, 2026

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Elm House Inn

Elm House Inn

2.5 out of 5
Central Napa
Save 100% on your flight
Price was $529, price is now $383 per person
$383
per person
Nov 20 - Nov 23
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
Price was $858, price is now $603 per person
$603
per person
Dec 16 - Dec 19
found 22 hours ago
Roundtrip flight included
Denver (DEN) to Oakland (OAK)
Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

4 out of 5
Boyes Hot Springs
Save 100% on your flight
Price was $1,318, price is now $933 per person
$933
per person
Dec 3 - Dec 7
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Oakland (OAK)
White House Napa - Adults Only

White House Napa - Adults Only

4 out of 5
Napa Abajo
Save 100% on your flight
Price was $1,525, price is now $1,097 per person
$1,097
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Oakland (OAK)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Mira Vista

Hotel Mira Vista

2 out of 5
Save 100% on your flight
Price was $499, price is now $358 per person
$358
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

4 out of 5
Boyes Hot Springs
Save 100% on your flight
Price was $1,452, price is now $896 per person
$896
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
Marina Village Inn

Marina Village Inn

2 out of 5
Save 100% on your flight
Price was $690, price is now $440 per person
$440
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
Save 100% on your flight
Price was $1,254, price is now $846 per person
$846
per person
Dec 18 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Alaska Airlines
Sat, Oct 17 - Tue, Oct 20
SAN
San Diego Intl.
STS
Sonoma County
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Oct 17 from San Diego Intl. to Sonoma County, returning Tue, Oct 20, priced at $119 found 1 day ago
Bargain Flight
Tue, Oct 6 - Sun, Oct 18
SAN
San Diego Intl.
OAK
Oakland Intl.
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Oct 6 from San Diego Intl. to Oakland Intl., returning Sun, Oct 18, priced at $151 found 4 days ago
Bargain Flight
Thu, Dec 31 - Tue, Jan 5
SEA
Seattle - Tacoma Intl.
OAK
Oakland Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Dec 31 from Seattle - Tacoma Intl. to Oakland Intl., returning Tue, Jan 5, priced at $157 found 1 day ago
Frontier Airlines
Thu, Oct 29 - Sun, Nov 1
LAX
Los Angeles Intl.
OAK
Oakland Intl.
$163 Roundtrip, found 13 hours ago
$163
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Los Angeles Intl. to Oakland Intl., returning Sun, Nov 1, priced at $163 found 13 hours ago