Chalk Hill Vacation Packages for 2025
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.
City24 Hotel Little Italy Mission Hills
Middletown
Save 100% on your flight
Price was $774, price is now $488 per person
$488
per person
Jan 17 - Jan 21
found 11 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
Stay at this 4.5-star luxury aparthotel in San Diego. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Popular attractions Port of San Diego and San Diego Zoo are located nearby.
The Sofia Hotel
Downtown San Diego
Save 100% on your flight
Price was $1,722, price is now $888 per person
$888
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Stay at this 3.5-star 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 USS Midway Museum are located nearby.
Margaritaville Hotel San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,425, price is now $780 per person
$780
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Stay at this 4-star hotel in San Diego. Enjoy a rooftop terrace, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Petco Park and Port of San Diego are located nearby.
Sand Castle Inn
Save 100% on your flight
Price was $1,093, price is now $619 per person
$619
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach motel in Imperial Beach. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions San Diego Bay and Las Americas Premium Outlets are located nearby.
Palihotel San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,391, price is now $864 per person
$864
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Stay at this 4-star hotel in San Diego. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Petco Park and Port of San Diego are located nearby.
Hilton San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,061, price is now $666 per person
$666
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
Stay at this 4-star business-friendly hotel in San Diego. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Petco Park and USS Midway Museum 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
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
3421 Cleveland Ave, Santa Rosa, CA
10.62 km from city center
Stay at this 3-star business-friendly hotel in Santa Rosa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the bar in our reviews. ...
Oxford Suites Sonoma County
67 Golf Course Drive W., Rohnert Park, CA
23.09 km from city center
Stay at this 3-star business-friendly hotel in Rohnert Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
The Lodge at Bodega Bay
103 Coast Highway 1, Bodega Bay, CA
36.69 km from city center
Stay at this 4-star hotel in Bodega Bay. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
The Inn at the Tides
800 Coast Hwy One, Bodega Bay, CA
36.45 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 ...
Quality Inn Petaluma - Sonoma
5100 Montero Way, Petaluma, CA
33.43 km from city center
Book a stay at this business-friendly hotel in Petaluma. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton
5870 Labath Ave, Rohnert Park, CA
24.33 km from city center
Stay at this 4-star business-friendly hotel in Rohnert Park. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar ...
DoubleTree by Hilton Sonoma - Wine Country
1 Doubletree Dr, Rohnert Park, CA
23.02 km from city center
Stay at this 4-star golf hotel in Rohnert Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Hyatt Regency Sonoma Wine Country
170 Railroad Street, Santa Rosa, CA
15.09 km from city center
Stay at this 4-star hotel in Santa Rosa. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in ...
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
2777 4th St, Santa Rosa, CA
14.38 km from city center
Stay at this 4-star 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 ...
Budget Inn
6298 Redwood Dr., Rohnert Park, CA
24.68 km from city center
Stay at this motel in Rohnert Park. Enjoy free WiFi, free parking, and a 24-hour front desk. 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
Stay at this 5-star luxury hotel in Calistoga. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
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.
Tue, Dec 9 - Sun, Dec 14
PDX
Portland Intl.
STS
Sonoma County
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Sun, Dec 7 - Fri, Dec 12
PDX
Portland Intl.
STS
Sonoma County
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Wed, Dec 10 - Sat, Dec 13
PDX
Portland Intl.
STS
Sonoma County
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Tue, Dec 9 - Fri, Dec 12
PDX
Portland Intl.
STS
Sonoma County
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago