Find Hotels with Connecting Rooms in Healdsburg, CA

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Top Healdsburg Hotels with Connecting Rooms

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 star property
Windsor
9.2 out of 10, Wonderful, (1255)
"Super nice! And friendly staff "
United States
Georgina
$95 nightly
The price is $108
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
Windsor
9.2 out of 10, Wonderful, (1001)
"Great staff and vibe"
United States
Curtis
$110 nightly
The price is $126
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hampton Inn & Suites Windsor - Sonoma Wine Country

Dry Creek Inn MOD Collection by Sonesta

3.0 star property
Healdsburg
8.0 out of 10, Very Good, (1007)
"Clean room, staff was very friendly and checking in was easy"
United States
Benjamin
$144 nightly
The price is $167
Dec 10 - Dec 11
Total with taxes and fees
Dry Creek Inn MOD Collection by Sonesta

Fairview Inn and Suites

3.0 star property
Healdsburg
7.8 out of 10, Good, (1002)
"Rooms are always clean and well maintained and staff are always friendly."
United States
Nicholas
$118 nightly
The price is $137
Dec 14 - Dec 15
Total with taxes and fees
Fairview Inn and Suites

Best Western Plus Wine Country Inn & Suites

2.5 star property
Santa Rosa
7.8 out of 10, Good, (1003)
"Very good breakfast. Lots of choices!"
United States
Linda
$102 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
Best Western Plus Wine Country Inn & Suites

Hilton Garden Inn Sonoma County Airport

3.0 star property
Santa Rosa
9.2 out of 10, Wonderful, (1003)
"Our go-to place when we're in Santa Rosa. Clean, quiet and a great breakfast. "
United States
Lisa
$111 nightly
The price is $127
Dec 15 - Dec 16
Total with taxes and fees
Hilton Garden Inn Sonoma County Airport

Vinarosa Resort & Spa

4.0 star property
Santa Rosa
9.4 out of 10, Exceptional, (804)
"Amazing place"
United States
Robert
$306 nightly
The price is $349
Dec 22 - Dec 23
Total with taxes and fees
Vinarosa Resort & Spa

Hotel Healdsburg

4.0 star property
Healdsburg
9.2 out of 10, Wonderful, (431)
"Lovely hotel in the heart of Healdsburg. Wonderful stay. "
United States
Erica
$444 nightly
The price is $516
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hotel Healdsburg

Cottages at Little Saint

4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (68)
"It was very easy to check in and our cottage was very comfortable. "
United States
Glenn
$326 nightly
The price is $379
Dec 17 - Dec 18
Total with taxes and fees
Cottages at Little Saint

Montage Healdsburg

5.0 star property
Healdsburg
9.6 out of 10, Exceptional, (115)
"Clean room, kind and helpful staff. Nice ambiance in vineyard. "
United States
Arthur
$698 nightly
The price is $812
Jan 5 - Jan 6, 2026
Total with taxes and fees
Montage Healdsburg
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.

Find out more about Healdsburg

Discover top Healdsburg attractions

Healdsburg, California, a gem in Sonoma County, offers an unforgettable experience for travelers. Start your adventure at the Healdsburg Plaza, where charming boutiques and gourmet restaurants surround a picturesque park, perfect for a family picnic. Just a short stroll away, the Healdsburg Museum showcases the town's rich history, providing fascinating insights into the region's wine culture. For wine enthusiasts, a visit to the nearby Dry Creek Valley is a must; here, you can explore world-class vineyards, many of which offer exclusive tastings and behind-the-scenes tours. Adventurous families can embark on a kayaking excursion along the Russian River, enjoying breathtaking views and the chance to spot local wildlife. Finally, unwind at one of Healdsburg's luxurious hotels, like the Hotel Healdsburg, where modern elegance meets top service, and indulge in a rejuvenating spa day or enjoy a meal at the acclaimed farm-to-table restaurant. Staying in the vibrant downtown area allows for easy access to all these experiences, ensuring that your family enjoys a memorable getaway filled with quality and convenience.

Find the best hotels with connecting rooms in Healdsburg

For travelers seeking accommodations that offer connecting rooms in Healdsburg, California, here are some top hotel options that provide the perfect environment for families or groups of friends. Each hotel features connecting room options to enhance your stay.

The River Belle Inn

  • Why it's great for extra space: The River Belle Inn is a charming choice with a perfect review rating of 10.0, making it an ideal accommodation for travelers who require connecting rooms. This Victorian-style hotel offers a beautiful and serene environment while ensuring guests have the space they need for relaxation and connection.
  • Other amenities: Guests are welcomed with free breakfast options and can enjoy the stunning river views from the terrace. Additional features include self-parking, daily housekeeping, and complimentary designer toiletries. The hotel also offers an onsite concierge service, access to kayaking, and nearby hiking and biking trails for outdoor enthusiasts.
  • Nearby attractions: Russian River - 0.0 miles, Healdsburg Museum - 0.6 miles, Pezzi King Winery - 0.06 miles

27 North

  • Why it's great for extra space: With a stellar review rating of 9.6, 27 North stands out as a chic option for travelers who need connecting rooms. This boutique hotel not only offers stylish accommodations but also provides connecting room availability, making it perfect for groups seeking a modern stay in Healdsburg.
  • Other amenities: Guests are treated to premium bedding, designer toiletries, and complimentary self-parking. The hotel features a concierge service to assist with local attractions and activities, as well as a cozy fireplace in select rooms. With a focus on luxury and comfort, the well-stocked minibar and daily housekeeping ensure a pleasant stay.
  • Nearby attractions: Healdsburg Plaza - 0.2 miles, Healdsburg Center for the Arts - 0.21 miles, Healdsburg Museum - 0.36 miles

Hotel Healdsburg

  • Why it's great for extra space: Hotel Healdsburg is an excellent choice for travelers needing connecting rooms, a remarkable review rating of 9.2. This upscale hotel offers a seamless experience with connecting room options, ensuring guests have the space they need while enjoying luxurious amenities like a full-service spa, outdoor pool, and complimentary breakfast.
  • Other amenities: Guests can indulge in manicures and pedicures, relax in the hot tub, or enjoy the beautiful terrace. The hotel features a concierge service, self-parking, and electric car charging stations for added convenience. With nearby golf options and spa treatments like Swedish massages and body wraps, guests will find plenty of ways to unwind during their stay.
  • Nearby attractions: Healdsburg Plaza - 0.1 miles, Healdsburg Center for the Arts - 0.21 miles, Healdsburg Museum - 0.26 miles

Best Western Dry Creek Inn

  • Why it's great for extra space: The Best Western Dry Creek Inn is a solid option for travelers looking for connecting rooms, with a guest review rating of 8.0. This welcoming hotel offers spacious rooms with connecting room options, making it ideal for families or groups seeking comfort and convenience at a reasonable price.
  • Other amenities: Guests can enjoy an outdoor pool and spa access, along with free cribs for younger travelers. A patio area provides a relaxing space to unwind, while the hotel also features a restaurant with kids' meals, free parking, and electric car charging stations. Outdoor activities, including winery tours nearby and golf options, enhance the overall experience.
  • Nearby attractions: Seghesio Family Vineyards - 0.72 miles, Simi Winery - 1.24 miles

Fairview Inn and Suites

  • Why it's great for extra space: Fairview Inn and Suites is a budget-friendly option for travelers needing connecting rooms, with a review rating of 7.6. This hotel provides comfortable accommodations and the flexibility of connecting room options, making it a practical choice for families and larger groups.
  • Other amenities: Travelers can enjoy an outdoor pool and hot tub, complemented by free onsite parking. The kitchenette in select suites adds convenience for longer stays, while the nearby winery tours and museums provide excellent local exploration opportunities. Free toiletries and a late check-out option enhance the overall experience.
  • Nearby attractions: Russian River - 0.53 miles, Healdsburg Plaza - 0.53 miles, Healdsburg Center for the Arts - 0.64 miles

Top Healdsburg Hotel Reviews

Frequently asked questions

How much do hotels with connecting rooms in Healdsburg cost?
Hotels with connecting rooms in Healdsburg range from $108 to $812 per night. This means lots of space for your entire crew at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with connecting rooms in Healdsburg?
A favorite is Hotel Les Mars. Kick back at this 4-star property which comes with hypo-allergenic bedding and a spa. H2Hotel is another hotel with connecting rooms worth a look. Spend your break at this 4-star option and make the most of conveniences such as mountain views and a terrace. You can choose from multiple hotels with connecting rooms in Healdsburg with a total average guest review rating of 8.8.
How many hotels with adjoining rooms are there in Healdsburg?
Pack your suitcase and pick from 4 hotels with adjoining rooms in Healdsburg. For a work-related trip, a weekend escape and everything in between, Expedia will help you find the ideal space in a few easy clicks.
What are the best cheap hotels with connecting rooms in Healdsburg?
Hampton Inn & Suites Windsor - Sonoma Wine Country is one of the most economical hotels with connecting rooms in Healdsburg and includes hypo-allergenic bedding and premium bedding. Another top choice that's budget friendly is Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel. Conveniences here include a sauna and WiFi. Rates for hotels with connecting rooms start at just $108 per night. Exploring free attractions in Healdsburg makes your vacation budget stretch even further. Dry Creek Vineyard and Mazzocco Winery are on the itineraries of many tourists. With the money you save, you can keep on sightseeing! This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the top motels with connecting rooms in Healdsburg?
Fairview Inn and Suites is a popular option, located around 0.4 mi south of downtown Healdsburg. With pool sun loungers and a swimming pool, this motel with connecting rooms is a great budget-friendly place to recharge your batteries between adventures.When you're ready to slip into some comfy sneakers and discover your surroundings, head for Dry Creek Vineyard. Mazzocco Winery is another terrific attraction worth seeing in Healdsburg.
Are there any family-friendly hotels with connecting rooms in Healdsburg?
Spend your family vacay at Hotel Les Mars, a 4-star option just a quick drive from town. Conveniences here include complimentary breakfast and laundry facilities. Another family-friendly hotel with connecting rooms is Hampton Inn & Suites Windsor - Sonoma Wine Country. Complimentary breakfast and laundry facilities help make this 2.5-star escape a favorite among guests. Once you've checked in and unpacked your bags, there are plenty of family-friendly attractions to discover in and around Healdsburg. Healdsburg Museum and Pacific Coast Air Museum guarantee a good time for young and old.
Are there any 5-star hotels with connecting rooms in Healdsburg?
Healdsburg unfortunately doesn't have any 5-star hotels with connecting rooms — but you and the crew can still enjoy a stylish getaway! Why not try Hotel Les Mars? Located around 0.2 miles from the downtown area, this 4-star favorite offers connecting rooms, as well as designer toiletries and concierge services. H2Hotel is another great choice just 0.1 miles from central Healdsburg. Also holding a 4-star rating, it features a terrace and a swimming pool, in addition to connecting rooms.
Why book your hotel with connecting rooms in Healdsburg with Expedia?
Booking a hotel with connecting rooms in Healdsburg is as easy as entering your travel dates and picking a place that checks your boxes. Want something affordable or luxurious, or a stay that also comes with a kitchen and laundry? Use Expedia's search filters to narrow your results even further and find your ideal pad.
How can I find cheap hotels with connecting rooms in Healdsburg?
Expedia is here to help you search for cheap hotels with connecting rooms in Healdsburg. To book the perfect stay in a couple of clicks, use our convenient filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Healdsburg near my hotel with connecting rooms?
Whatever you love doing, Healdsburg has plenty to keep you busy. Dry Creek Vineyard, Mazzocco Winery and Matrix Winery are on many travelers' lists. Don't forget to explore Chalk Hill Estate Vineyard, Hanna Winery and Vineyards and Wilson Winery either. With Expedia's Healdsburg hotel deals, you can discover more neat attractions like these with the cash you save.

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