--- title: "Chalk Hill Vacation Packages 2026 from $481 | Expedia" description: "Bundle Chalk Hill flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Chalk-Hill.d736342871657291776.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-15T21:00:04Z --- ![A group of large hot air balloons, including a yellow one with a face, and a white van with cartoon characters.](https://images.trvl-media.com/place/9542/b4ccdb92-b048-45af-b643-5a9cc297deeb.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Rick Alvarez # Chalk Hill Vacations from $481 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### Your Chalk Hill Vacation With a Chalk Hill vacation package, you can forget about planning hassles and simply focus on experiencing all this exciting destination has to offer. Not sure where to stay? [Windsor](https://www.expedia.com/Windsor.d9542.Destination-Travel-Guides) is one of the most popular cities to explore during a trip to Chalk Hill. Whether you're traveling for a couple of days or a couple of weeks, Expedia are here to help you customize your next Chalk Hill vacation. ## The Latest Chalk Hill Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A spacious lobby with modern furniture, large windows, and a high ceiling with hanging lights.](https://images.trvl-media.com/lodging/42000000/41510000/41504800/41504735/43ef19cb.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A pathway leading to a building labeled "LEGACY Hotel."](https://images.trvl-media.com/lodging/42000000/41510000/41504800/41504735/0bbd67f4.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 1 - Feb 6** ### [Legacy Resort Hotel & Spa + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-01/2027-02-06/?FromAirport=DEN&Destination=SAN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=41504735&dealMarker=&paandie=true&cabinClass=e) Mission Valley 5 nights **9.2/10** \- Wonderful (3,103 reviews) Roundtrip • Denver (DEN) - San Diego (SAN) DEN - SAN • Nonstop SAN - DEN • Nonstop [~~$881~~](https://www.expedia.com/) **$481** per traveler found 1 day ago - ![An outdoor seating area with tables and chairs, surrounded by a brick building with a glass entrance.](https://images.trvl-media.com/lodging/2000000/1580000/1573900/1573807/e14bea95.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A multi-story hotel with a brick facade, multiple windows, and a fire escape.](https://images.trvl-media.com/lodging/2000000/1580000/1573900/1573807/81065b81.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 1 - Feb 6** ### [The Sofia Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-01/2027-02-06/?FromAirport=DEN&Destination=SAN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1573807&dealMarker=&paandie=true&cabinClass=e) Downtown San Diego 5 nights **8.8/10** \- Excellent (2,785 reviews) Roundtrip • Denver (DEN) - San Diego (SAN) DEN - SAN • Nonstop SAN - DEN • Nonstop [~~$1,119~~](https://www.expedia.com/) **$543** per traveler found 1 day ago - ![A modern outdoor area with a bench, a planter, and a view of a lush green forest.](https://images.trvl-media.com/lodging/7000000/6120000/6117200/6117111/ebd066d1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern building with a wooden facade, a green awning, and a staircase leading to the entrance.](https://images.trvl-media.com/lodging/7000000/6120000/6117200/6117111/1ab57535.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 30 - Feb 5** ### [SIRTAJ - Beverly Hills + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-30/2027-02-05/?FromAirport=DAL&Destination=LAX&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6117111&dealMarker=&paandie=true&cabinClass=e) South of Wilshire 6 nights **8.2/10** \- Very good (1,004 reviews) Roundtrip • Dallas (DAL) - Los Angeles (LAX) DAL - LAX • Nonstop LAX - DAL • Nonstop [~~$1,505~~](https://www.expedia.com/) **$739** per traveler found 1 day ago - ![A modern living room with a fireplace, a round coffee table, and a sofa.](https://images.trvl-media.com/lodging/116000000/115910000/115904800/115904724/2fd260a2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern bedroom with a large bed, a wall mural, a hanging light fixture, and a window with curtains.](https://images.trvl-media.com/lodging/116000000/115910000/115904800/115904724/ed9ef0f4.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 28 - Feb 2** ### [Marbella Lane - 3BR Designer Near Valley Fair + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-28/2027-02-02/?FromAirport=EWR&Destination=SJC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115904724&dealMarker=&paandie=true&cabinClass=e) San Jose 5 nights Roundtrip • New York (EWR) - San Jose (SJC) EWR - SJC • 1 stop SJC - EWR • 1 stop [~~$2,413~~](https://www.expedia.com/) **$1,385** per traveler found 1 day ago - ![A hotel with multiple floors, a rooftop pool, and a central courtyard.](https://images.trvl-media.com/lodging/2000000/1120000/1117700/1117693/0db99a00.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A restaurant with a glass enclosure, brick facade, and outdoor seating area.](https://images.trvl-media.com/lodging/2000000/1120000/1117700/1117693/7680d8f6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 1 - Feb 6** ### [Margaritaville Hotel San Diego Gaslamp Quarter + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-01/2027-02-06/?FromAirport=DEN&Destination=SAN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1117693&dealMarker=&paandie=true&cabinClass=e) Downtown San Diego 5 nights **9.0/10** \- Wonderful (1,598 reviews) "The room was very clean and daily service was much appreciated. The only complaint we had was the lighting in our bedroom room and bathroom were minimal." Reviewed November 14, 2026 Roundtrip • Denver (DEN) - San Diego (SAN) DEN - SAN • Nonstop SAN - DEN • Nonstop [~~$1,109~~](https://www.expedia.com/) **$647** per traveler found 1 day ago ## Discover the most popular places to visit in Chalk Hill ### Safari West Rating: 8.8/10 (257 reviews) Explore the lovely green spaces of Safari West and also enjoy the biking trails in Santa Rosa. Amble around this romantic area's riverfront and enjoy its top-notch restaurants. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6208250) ### Chalk Hill Estate Vineyard Rating: 8.4/10 (12 reviews) You can enjoy a tasting or tour at Chalk Hill Estate Vineyard during your travels to Healdsburg. Stroll along the area's riverfront, or simply savor its top-notch restaurants. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6240787) ### Windsor Oaks Vineyards Rating: 9.6/10 (5 reviews) 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 top-notch restaurants. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327443) ### Guerro Fernandez You can enjoy a tasting or tour at Guerro Fernandez during your travels to Windsor. Check out the wineries or top-notch restaurants in this family-friendly area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=873861854588559360) ## Chalk Hill Hotel Deals ### [Hampton Inn & Suites Windsor - Sonoma Wine Country](https://www.expedia.com/Windsor-Hotels-Hampton-Inn-Suites-Windsor-Sonoma-Wine-Country.h2292819.Hotel-Information) ![A hotel entrance with a stone facade, a sign for Hampton Suites, and bicycles parked outside.](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292819/664c2ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 8937 Brooks Road South, Windsor, CA, 95492, US - Location: 3 mi from Chalk Hill - Star rating: 2.5/5 - Guest rating: 9.2/10 (Wonderful, 1004 reviews) - Price: $122 nightly, $140 total, Nov 22 - Nov 23, Total with taxes and fees ### [Holiday Inn Express® Windsor Sonoma Wine Country by IHG](https://www.expedia.com/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.Hotel-Information) ![A Holiday Inn Express sign with a landscaped area in front, including a fountain and flowering plants.](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/4f551039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 8865 Conde Lane, Windsor, CA, 95492, US - Location: 3.2 mi from Chalk Hill - Star rating: 2.5/5 - Guest rating: 9.2/10 (Wonderful, 1302 reviews) - Price: $99 nightly, $113 total, Dec 14 - Dec 15, Total with taxes and fees - Review: The coffee was exceptional, and the beds were incredibly comfortable ### [Holiday Inn Windsor Wine Country by IHG](https://www.expedia.com/Windsor-Hotels-Holiday-Inn-Windsor-Wine-Country.h13235845.Hotel-Information) ![A modern interior with a spiral staircase, a beige sofa, two armchairs, and a patterned rug.](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/18765525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 8755 Old Redwood Hwy, Windsor, CA, 95492, US - Location: 3 mi from Chalk Hill - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 1044 reviews) - Price: $111 nightly, $127 total, Dec 16 - Dec 17, Total with taxes and fees ### [La Quinta Inn & Suites Santa Rosa Sonoma](https://www.expedia.com/Santa-Rosa-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Santa-Rosa.h51310420.Hotel-Information) ![A modern hotel with a prominent sign, a covered entrance, and a parking area.](https://images.trvl-media.com/lodging/52000000/51320000/51310500/51310420/f3caac53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 111 Commercial Court, Santa Rosa, CA, 95407, US - Location: 10.6 mi from Chalk Hill - Star rating: 3/5 - Guest rating: 9/10 (Wonderful, 1191 reviews) - Price: $127 nightly, $147 total, Nov 22 - Nov 23, Total with taxes and fees ### [Hampton Inn & Suites Santa Rosa Sonoma Wine Country](https://www.expedia.com/Santa-Rosa-Hotels-Hampton-Inn-Suites-Santa-Rosa-Sonoma-Wine-Country.h83127055.Hotel-Information) ![A reception desk with a wooden and white design, a wall sign reading "WELCOME TO THE GOLDEN STATE," and a display of snacks and beverages.](https://images.trvl-media.com/lodging/84000000/83130000/83127100/83127055/b1eec51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3815 AIRWAY DR, Santa Rosa, CA, 95403, US - Location: 6 mi from Chalk Hill - Star rating: 2.5/5 - Guest rating: 9.4/10 (Exceptional, 638 reviews) - Price: $114 nightly, $132 total, Dec 5 - Dec 6, Total with taxes and fees - Review: The room was clean and breakfast was great! ### [Hilton Garden Inn Sonoma County Airport](https://www.expedia.com/Santa-Rosa-Hotels-Hilton-Garden-Inn-Sonoma-County-Airport.h1865821.Hotel-Information) ![A covered outdoor seating area with two lounge chairs and a stone fireplace.](https://images.trvl-media.com/lodging/2000000/1870000/1865900/1865821/96c44de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 417 Aviation Blvd, Santa Rosa, CA, 95403, US - Location: 4 mi from Chalk Hill - Star rating: 3/5 - Guest rating: 9.2/10 (Wonderful, 1000 reviews) - Price: $114 nightly, $130 total, Dec 5 - Dec 6, Total with taxes and fees - Review: The room was very clean and spacious.. The staff were also very helpful and friendly! ### [Holiday Inn Express Santa Rosa North by IHG](https://www.expedia.com/Santa-Rosa-Hotels-Holiday-Inn-Express-Santa-Rosa-North.h522532.Hotel-Information) ![A buffet with various food items, including omelets and other dishes, displayed in metal serving trays.](https://images.trvl-media.com/lodging/1000000/530000/522600/522532/eacda366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2632 Cleveland Ave, Santa Rosa, CA, 95403, US - Location: 7.5 mi from Chalk Hill - Star rating: 2.5/5 - Guest rating: 8.4/10 (Very good, 551 reviews) - Price: $105 nightly, $122 total, Dec 12 - Dec 13, Total with taxes and fees ### [Hampton Inn & Suites Rohnert Park - Sonoma County](https://www.expedia.com/Rohnert-Park-Hotels-Hampton-Inn-Suites-Rohnert-Park-Sonoma-County.h1747239.Hotel-Information) ![A Hampton Inn & Suites hotel with a modern facade, a flag, and a well-maintained entrance.](https://images.trvl-media.com/lodging/2000000/1750000/1747300/1747239/50e5b27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 6248 Redwood Dr, Rohnert Park, CA, 94928, US - Location: 15.3 mi from Chalk Hill - Star rating: 2.5/5 - Guest rating: 8.8/10 (Excellent, 1002 reviews) - Price: $86 nightly, $99 total, Nov 20 - Nov 21, Total with taxes and fees - Review: "My family and I were here for my son's soccer tournament as soon as we arrived we could not wait to check in, and Lisa was beyond amazing! I appreciated how easy going and the process flow just to check in and get my room key within 5minutes. She was very helpful and sweet. Once we got to our rooms our beds and bathroom was spotless! We had breakfast in the morning and their buffet menu from eggs, sausages, pastries and 4 different flavors of juice was sooo yummy!! The best part was the 24/7... 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. 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[Fort Point National Historical Site](https://www.expedia.com/Fort-Point-National-Historical-Site-San-Francisco.d6069421.Vacation-Attraction) - [Windsor Vacations](https://www.expedia.com/Windsor.d9542.Destination-Travel-Guides) - [Old Faithful Geyser of California](https://www.expedia.com/Old-Faithful-Geyser-Of-California-Calistoga.d6065829.Vacation-Attraction) - [Ferryboat Eureka](https://www.expedia.com/Ferryboat-Eureka-Fishermans-Wharf.d6155184.Vacation-Attraction) - [University of California](https://www.expedia.com/University-Of-California-Oakland.d6069427.Vacation-Attraction) - [Safari West](https://www.expedia.com/Safari-West-Santa-Rosa.d6208250.Vacation-Attraction) - [Powell's Sweet Shoppe - Windsor](https://www.expedia.com/Powells-Sweet-Shoppe-Windsor-Windsor.d553248621532640709.Vacation-Attraction) - [Letterman Digital and New Media Arts Center](https://www.expedia.com/Letterman-Digital-And-New-Media-Arts-Center-Presidio.d553248633956255817.Vacation-Attraction) - [Columbus Tower](https://www.expedia.com/Columbus-Tower-Downtown-San-Francisco.d553248621533114313.Vacation-Attraction) - [Berkeley Marina](https://www.expedia.com/Berkeley-Marina-Berkeley-Marina.d6063227.Vacation-Attraction) - [Pacific-Union Club](https://www.expedia.com/Pacific-Union-Club-Downtown-San-Francisco.d553248621533114844.Vacation-Attraction) - [Historic Berkeley](https://www.expedia.com/Historic-Berkeley-Downtown-Berkeley.d6335740.Vacation-Attraction) - [Castello di Amorosa](https://www.expedia.com/Castello-Di-Amorosa-Calistoga.d6208243.Vacation-Attraction) - [Coastal Trail](https://www.expedia.com/Coastal-Trail-Sea-Cliff.d553248621533113746.Vacation-Attraction) - [Walter S. Johnson Park](https://www.expedia.com/Walter-S-Johnson-Park-Marina-District.d6155712.Vacation-Attraction) - [Westfield San Francisco Centre](https://www.expedia.com/Westfield-San-Francisco-Centre-Downtown-San-Francisco.d6132591.Vacation-Attraction) - [Hanna Winery and Vineyards](https://www.expedia.com/Hanna-Winery-And-Vineyards-Healdsburg.d6240834.Vacation-Attraction) - [Presidio Army Museum](https://www.expedia.com/Presidio-Army-Museum-Marina-District.d6155409.Vacation-Attraction) - [Uc Theatre Taube Family Music Hall](https://www.expedia.com/UC-Theatre-Taube-Family-Music-Hall-Downtown-Berkeley.d553248633894912029.Vacation-Attraction) - [Golden Gate Fields](https://www.expedia.com/Golden-Gate-Fields-Oakland.d502579.Vacation-Attraction) - [Emeryville Marina](https://www.expedia.com/Emeryville-Marina-Oakland.d553248621532640482.Vacation-Attraction) - [Kendall-Jackson Wine Estate and Gardens](https://www.expedia.com/Kendall-Jackson-Wine-Estate-And-Gardens-Fulton.d6068461.Vacation-Attraction) - [San Francisco Carousel](https://www.expedia.com/San-Francisco-Carousel-Fishermans-Wharf.d553248621533114439.Vacation-Attraction) - [Healdsburg Vacations](https://www.expedia.com/Healdsburg.d8322.Destination-Travel-Guides) - [The Cannery at Del Monte Square](https://www.expedia.com/The-Cannery-At-Del-Monte-Square-Fishermans-Wharf.d6192733.Vacation-Attraction) - [Paradise Beach Park](https://www.expedia.com/Paradise-Beach-Park-Tiburon.d6335102.Vacation-Attraction) - [Ss Jeremiah O'Brien](https://www.expedia.com/SS-Jeremiah-OBrien-Fishermans-Wharf.d6155490.Vacation-Attraction) - [San Francisco Maritime National Historical Park](https://www.expedia.com/San-Francisco-Maritime-National-Historical-Park-Fishermans-Wharf.d6155539.Vacation-Attraction) - [Van Ness Avenue](https://www.expedia.com/Van-Ness-Avenue-Downtown-San-Francisco.d3000663410.Vacation-Attraction) - [Saints Peter and Paul Church](https://www.expedia.com/Saints-Peter-And-Paul-Church-North-Beach.d6155492.Vacation-Attraction) - [Chickering American River Reserve](https://www.expedia.com/Chickering-American-River-Reserve-Oakland.d553248621532640497.Vacation-Attraction) - [China Beach](https://www.expedia.com/China-Beach-Sea-Cliff.d6155072.Vacation-Attraction) - [San Francisco Bay Model Visitor Center](https://www.expedia.com/San-Francisco-Bay-Model-Visitor-Center-Sausalito.d6335163.Vacation-Attraction) - [Golden Gate Bridge](https://www.expedia.com/Golden-Gate-Bridge-San-Francisco.d508803.Vacation-Attraction) - [Armstrong Redwoods State Park](https://www.expedia.com/Armstrong-Redwoods-State-Park-Guerneville.d6087093.Vacation-Attraction) - [Conservatory of Flowers](https://www.expedia.com/Conservatory-Of-Flowers-Golden-Gate.d6069419.Vacation-Attraction) - [Yerba Buena Gardens](https://www.expedia.com/Yerba-Buena-Gardens-Downtown-San-Francisco.d6155654.Vacation-Attraction) - [Simi Winery](https://www.expedia.com/Simi-Winery-Healdsburg.d6327412.Vacation-Attraction) - [University of California Museum of Paleontology](https://www.expedia.com/University-Of-California-Museum-Of-Paleontology-Oakland.d553248621532640498.Vacation-Attraction) - [Marina District Vacations](https://www.expedia.com/Marina-District.d130032.Destination-Travel-Guides) - [San Francisco National Cemetery](https://www.expedia.com/San-Francisco-National-Cemetery-Presidio.d6155707.Vacation-Attraction) - [Mrs. Doubtfire House](https://www.expedia.com/Mrs-Doubtfire-House-Pacific-Heights.d6227876.Vacation-Attraction) - [Albany Vacations](https://www.expedia.com/Albany.d179368.Destination-Travel-Guides) - [Fort Cronkhite](https://www.expedia.com/Fort-Cronkhite-Sausalito.d553248621558560594.Vacation-Attraction) - [Ripley's Believe It Or Not Museum](https://www.expedia.com/Ripleys-Believe-It-Or-Not-Museum-Fishermans-Wharf.d6151470.Vacation-Attraction) - [San Francisco Vacations](https://www.expedia.com/San-Francisco.d178305.Destination-Travel-Guides) - [Fort Mason](https://www.expedia.com/Fort-Mason-Marina-District.d6155188.Vacation-Attraction) - [Hawk Hill](https://www.expedia.com/Hawk-Hill-Sausalito.d553248621533114420.Vacation-Attraction) - [Robert Lowie Museum of Anthropology](https://www.expedia.com/Robert-Lowie-Museum-Of-Anthropology-Downtown-Berkeley.d553248621532640494.Vacation-Attraction) - [San Francisco Maritime Museum](https://www.expedia.com/San-Francisco-Maritime-Museum-Fishermans-Wharf.d6155465.Vacation-Attraction) - [Chateau Montelena Winery](https://www.expedia.com/Chateau-Montelena-Winery-Calistoga.d6239667.Vacation-Attraction) - [Bohemian Grove](https://www.expedia.com/Bohemian-Grove-Sebastopol.d6087095.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. 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