Chalk Hill Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Jennifer Hill
Chalk Hill Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel
Downtown San Diego
Save 100% on your flight
Price was $1,345, price is now $695 per person
$695
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Book a stay at this historic hotel in San Diego. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Diego and Petco Park are located nearby.
Paradise Point Resort & Spa
Mission Bay
Save 100% on your flight
Price was $1,887, price is now $1,091 per person
$1,091
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Book a stay at this beach resort in San Diego. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Mission Bay and Port of San Diego are located nearby.
Sentral Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,147, price is now $698 per person
$698
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Petco Park and Port of San Diego are located nearby.
Pacific View Inn
Pacific Beach
Save 100% on your flight
Price was $1,447, price is now $934 per person
$934
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Book a stay at this beach hotel in San Diego. Enjoy free WiFi, a beach locale, and surfing/body boarding on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mission Bay and Mission Beach are located nearby.
San Diego Marriott La Jolla
University City
Save 100% on your flight
Price was $1,335, price is now $899 per person
$899
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Book a stay at this business-friendly hotel in La Jolla. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions La Jolla Beach and Torrey Pines Golf Course are located nearby.
The Beau Downtown San Diego Gaslamp Quar
Downtown San Diego
Save 100% on your flight
Price was $1,176, price is now $803 per person
$803
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Popular attractions Petco Park and Port of San Diego are located nearby.
Top Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
5.07 km from city center
Book a stay at this golf hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
4.9 km from city center
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
4.83 km from city center
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Oxford Suites Sonoma County
67 Golf Course Drive W. Rohnert Park CA
23.09 km from city center
Book a stay at this business-friendly hotel in Rohnert Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
3421 Cleveland Ave Santa Rosa CA
10.62 km from city center
Book a stay at this business-friendly hotel in Santa Rosa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ...
The Inn at the Tides
800 Coast Hwy One Bodega Bay CA
36.4 km from city center
Stay at this hotel in Bodega Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
DoubleTree by Hilton Sonoma - Wine Country
1 Doubletree Dr Rohnert Park CA
23.02 km from city center
Book a stay at this golf hotel in Rohnert Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
2777 4th St Santa Rosa CA
14.38 km from city center
Book a stay at this spa hotel in Santa Rosa. Enjoy 2 outdoor pools, a full-service spa, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
El Bonita Motel
195 Main Street St. Helena CA
27.39 km from city center
Stay at this motel in St. Helena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hyatt Regency Sonoma Wine Country
170 Railroad Street Santa Rosa CA
15.09 km from city center
Stay at this hotel in Santa Rosa. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Solage, Auberge Collection
755 Silverado Trl Calistoga CA
16.36 km from city center
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 ...
The Lodge at Bodega Bay
103 Coast Highway 1 Bodega Bay CA
36.69 km from city center
Stay at this hotel in Bodega Bay. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
La Quinta Inn & Suites Santa Rosa Sonoma
111 Commercial Court Santa Rosa CA
17.12 km from city center
Book a stay at this business-friendly hotel in Santa Rosa. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Dec 25 - Sun, Dec 28
SAN
San Diego Intl.
STS
Sonoma County
$542 Roundtrip, found 3 days ago
$542
Roundtrip
found 3 days ago
Thu, Dec 25 - Sun, Dec 28
SAN
San Diego Intl.
STS
Sonoma County
$562 Roundtrip, found 3 days ago
$562
Roundtrip
found 3 days ago
Thu, Dec 25 - Sun, Dec 28
SAN
San Diego Intl.
STS
Sonoma County
$562 Roundtrip, found 3 days ago
$562
Roundtrip
found 3 days ago
Thu, Dec 25 - Sun, Dec 28
SAN
San Diego Intl.
STS
Sonoma County
$572 Roundtrip, found 3 days ago
$572
Roundtrip
found 3 days ago