Winery Hotels in Healdsburg, CA
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Healdsburg Winery Hotels

Best Western Dry Creek Inn
198 Dry Creek Rd Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $138 total per night
$138 total
Dec 27 - Dec 28
Total with taxes and fees
Renovated in 2022, Dry Creek Inn MOD Collection by Sonesta offers an outdoor pool, free WiFi in public areas, and a business center. Self parking is available for USD 5.00 per day. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this family-friendly hotel include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Pool
Pet friendly

Healdsburg Inn on the Plaza, A Four Sisters Inn
112 Matheson Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$210 nightly
The price is $244 total per night
$244 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests of Healdsburg Inn on the Plaza, A Four Sisters Inn enjoy access to free WiFi in public areas, a business center, and coffee in a common area. If you plan to drive, free offsite parking is available. Front-desk staff can assist with securing valuables, tours or tickets, and luggage storage. Additional amenities include free use of bicycles, free newspapers, and a fireplace in the lobby.
Breakfast included
Free WiFi

The Madrona
1001 Westside Road Healdsburg CA
$562 nightly
The price is $642 total per night
$642 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Guests of The Madrona have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free valet parking if you drive. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, securing valuables, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Other amenities at this adults-only hotel include a seasonal outdoor pool, a meeting room, and express check-out.
Pool
Breakfast included

Calderwood Inn
25 West Grant Street Healdsburg CA
$181 nightly
The price is $210 total per night
$210 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
A local mainstay since 1903, Calderwood Inn offers free WiFi in public areas, a library, and a terrace. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a garden and a picnic area.
Breakfast included
Pet friendly

Fairview Inn and Suites
74 Healdsburg Ave Healdsburg CA
Free Cancellation
$118 nightly
The price is $137 total per night
$137 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Fairview Inn and Suites, guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. You can take advantage of free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Other amenities at this hot springs motel include a seasonal outdoor pool and express check-out.
Pool
Hot Tub

H2Hotel
219 Healdsburg Ave Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$266 nightly
The price is $309 total per night
$309 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
Guests of H2Hotel have access to a full-service spa, an outdoor pool, and conference space. Multilingual staff at the 24-hour front desk can assist with luggage storage, concierge services, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include a business center, express check-out, and free newspapers.
Pool
Spa

Grape Leaf Inn
539 Johnson Street Healdsburg CA
$219 nightly
The price is $254 total per night
$254 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Guests of Grape Leaf Inn enjoy an outdoor pool, free WiFi in public areas, and spa treatment rooms. You can take advantage of free parking if you drive. Helpful staff is there to provide concierge services, as well as offer insight about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this boutique bed & breakfast include a library, express check-in, and express check-out.
Pool
Spa

27 North
27 North St Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$640 nightly
The price is $744 total per night
$744 total
Dec 28 - Dec 29
Total with taxes and fees
At 27 North, guests have access to free WiFi in public areas, meeting rooms, and a library. If you plan to drive, free parking is available. The front desk is staffed 24/7 to help with securing valuables, concierge services, and luggage storage. Other amenities at this luxury hotel include free newspapers, laundry facilities, and a banquet hall.
Parking included
Free WiFi

Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza
Healdsburg CA
At this vacation home, guests enjoy features like an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly vacation home include laundry facilities and barbecue grills.
Pool
Hot Tub

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Healdsburg CA
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer

Hotel Vinea, a Travelodge by Wyndham
178 Dry Creek Rd Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $120 total per night
$120 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hotel Vinea, a Travelodge by Wyndham features free WiFi in public areas and a picnic area. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a vending machine and a garden.
Breakfast included
Parking included

Honor Mansion
891 Grove Street Healdsburg Healdsburg CA
Honor Mansion offers an outdoor pool, free WiFi in public areas, and an outdoor tennis court. Free parking is included with your stay. Staff members are on hand to provide concierge services and luggage storage. Additional amenities include a 24-hour business center, a garden, and a picnic area.
Pool
Breakfast included

Hotel Healdsburg
25 Matheson St Healdsburg CA
Free Cancellation
Reserve now, pay when you stay
$444 nightly
The price is $516 total per night
$516 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Hotel Healdsburg enjoy a full-service spa, an outdoor pool, and a gym. You can put free parking to good use if you drive. The front desk is staffed 24/7 to help with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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.
Healdsburg hotels essential information
Accommodation | 501 hotels |
|---|---|
Lowest Price | $120 |
Highest Price | $744 |
Popular hotels | Best Western Dry Creek Inn, Healdsburg Inn on the Plaza, A Four Sisters Inn, The Madrona, Calderwood Inn, Fairview Inn and Suites, H2Hotel, Grape Leaf Inn, 27 North, Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza, Modern Wine Country Cottage in Historic Healdsburg, Premiere Location, Hotel Vinea, a Travelodge by Wyndham, Honor Mansion, Hotel Healdsburg, Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards |
Recent Winery Hotels Reviews

Hotel Vinea, a Travelodge by Wyndham
5/5 Excellent
"♡"
A verified traveler stayed at Hotel Vinea, a Travelodge by Wyndham
Posted 7 days ago



