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4- and 5-star hotels in Healdsburg
A shortlist of 12 four- and five-star hotels in Healdsburg, California, chosen from the stays our site lists. It is for travellers who want wine-country comfort in town or just outside it, from a 5-star resort to small guesthouses.
Staying in Healdsburg
Healdsburg sits at the heart of Sonoma County wine country, within easy reach of the Russian River and the vineyards of Dry Creek and Alexander valleys. Visitors come for tasting rooms around the plaza, vineyard drives, and the mix of inns, small hotels and resort-style estates that dot the town and its outskirts.
The stays on this list fall into two groups. Several sit on or just off Healdsburg Avenue and nearby streets in the centre — Hotel Healdsburg on Matheson St, H2Hotel and Two Thirty Five on Healdsburg Avenue, 27 North on North St, Grape Leaf Inn on Johnson Street, Healdsburg Modern Cottages on Foss Street and Honor Mansion on Grove Street — so the plaza, shops and restaurants are close at hand. Others, such as Montage Healdsburg on Montage Way, The Madrona on Westside Road and Bella Villa Messina on Burgundy Rd, are set slightly out of town amid gardens and vineyards. Couples on a wine-country break, families who want pools and family rooms, and business travellers needing meeting space and Wi-Fi are all catered for.
The shortlist
Ranked by hotel class, then guest rating and number of reviews.
Montage Healdsburg
100 Montage Way, Healdsburg, United States
Best for: Families · Drivers
- Kids pool
- Sauna
- Parking
Why stay hereMontage Healdsburg is a 5-star resort with a 4.6 guest rating across 409 reviews, set on Montage Way. Guests can spend the day at archery, then unwind in the fitness centre, the jacuzzi or the kids pool. Bars, a market and a beauty salon sit alongside family rooms and a concierge, so longer stays with children are easy to arrange. It suits travellers who want a full-service resort with plenty to do on site.
See Montage HealdsburgThe Madrona
1001 Westside Road, Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Car parking
- Breakfast
Why stay hereThe Madrona earns a 4.9 guest rating from 133 reviews, the strongest on this list, on Westside Road. An outdoor pool and a garden terrace give the 4-star property room to breathe, while the fitness centre and restaurant cover everyday needs. Multilingual staff, a business centre and wedding services make it work for both leisure trips and small events. Couples and celebrations are the natural fit here.
See The MadronaHotel Healdsburg
25 Matheson St, Healdsburg, United States
Best for: Families · Drivers
- Outdoor pool
- Spa
- Free car parking
Why stay hereHotel Healdsburg sits on Matheson St, steps from the town's plaza, a 4-star address with a 4.6 rating from 306 guests. An outdoor pool and a fitness centre cover the active side of a stay, and the restaurant and bar mean dinner is an easy walk from your room. Bikes are available for riding out into the surrounding vineyards, and pets are welcome. Couples on a wine-country weekend and families taking the larger rooms both fit comfortably here.
See Hotel HealdsburgH2Hotel
219 Healdsburg Ave, Healdsburg, United States
Best for: Families · Drivers
- Outdoor pool
- Spa
- Parking
Why stay hereH2Hotel on Healdsburg Ave is a 4-star hotel with a 4.6 rating from 185 reviews. A salt water outdoor pool and a spa anchor the stay, with yoga and a golf course among the options for active guests. Pets are welcome, family rooms are available and valet parking is offered. The mix of spa time and outdoor activity suits couples and families who want downtime and movement in equal measure.
See H2HotelHonor Mansion
891 Grove Street Healdsburg, Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Spa
- Free car parking
Why stay hereHonor Mansion is a 4-star property on Grove Street with a 4.7 guest rating from 89 reviews. A garden and picnic area pair with an outdoor pool, and both a spa and a tennis court are on hand for guests. Breakfast and a buffet are provided, and free car parking keeps arrivals simple. The setting appeals to travellers who prefer a quieter house-style stay with sport and spa facilities close by.
See Honor MansionDowntown Suites One
415A Healdsburg Avenue, Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Free car parking
- Breakfast
Why stay hereDowntown Suites One on Healdsburg Avenue is a 4-star option rated 4.4 by 27 guests. The draw is the combination of an outdoor pool, free wifi and free car parking, with breakfast included and a meeting room available. It is wheelchair accessible. With this few reviews it remains something of an undiscovered choice, and it fits guests who need parking and a central address without extra frills.
See Downtown Suites OneHealdsburg Modern Cottages
425 Foss Street Healdsburg California 95448, Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Free car parking
- Wheelchair accessible
Why stay hereHealdsburg Modern Cottages on Foss Street is a 4-star property with a 4.2 rating from 5 reviews, so it is a small-scale affair. Guests have an outdoor pool, a garden and a terrace, plus concierge service and housekeeping. Free car parking and a shuttle service are offered, and the property is wheelchair accessible. It suits travellers who want cottage-style privacy with a pool and terrace rather than a large hotel.
See Healdsburg Modern CottagesGrape Leaf Inn
539 Johnson Street, Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Spa
- Free car parking
Why stay hereGrape Leaf Inn sits on Johnson Street as a 4-star property. An outdoor pool and spa are the main amenities, backed by a garden, patio and picnic area. Breakfast can be taken in the room, bike rental is available, and pets are allowed. Concierge service, express check-in and special diets are also covered. It fits guests who want a relaxed garden setting with breakfast brought to the door.
See Grape Leaf Inn27 North
27 North St, Healdsburg, United States
Best for: Drivers · Breakfast
- Free car parking
- Breakfast
- Pets allowed
Why stay here27 North on North St is a 4-star hotel with a broad activity list: golf, canoeing, horse riding and bike rental are all offered, along with massage. Rooms come with air conditioning, and the property has a restaurant, bar and room service. Breakfast is served and can also be taken in the room, and pets are allowed. It suits guests who plan to be out doing things and want a comfortable base with dining on site.
See 27 NorthUrban Luxe Loft
224 Healdsburg Ave., Healdsburg, United States
Best for: Drivers · Pool and spa
- Outdoor pool
- Free car parking
- Breakfast
Why stay hereUrban Luxe Loft on Healdsburg Ave. is a 4-star property built around in-room cooking, with a kitchen or kitchenette plus microwave, oven and refrigerator. There is an outdoor pool, and breakfast, coffee and free wifi are provided alongside free car parking. A meeting room is available for work. It suits longer stays and guests who prefer to prepare their own meals while keeping hotel facilities close.
See Urban Luxe LoftTwo Thirty Five
235 Healdsburg Ave Healdsburg Ca 95448 Usa Healdsburg Healdsburg, Healdsburg, United States
Best for: Drivers · Business trips
- Parking
- Free Wifi
Why stay hereTwo Thirty Five on Healdsburg Ave is a 4-star hotel with a restaurant, room service and a conference hall. Concierge service and a reception area handle the practical side, with lifts, non-smoking rooms and parking on site. Free wifi and internet access are provided throughout. The conference facilities and central address make it a sensible pick for guests mixing business meetings with time in town.
See Two Thirty FiveBella Villa Messina
316 Burgundy Rd, Healdsburg, United States
Best for: Families · Drivers
- Outdoor pool
- Spa
- Free car parking
Why stay hereBella Villa Messina on Burgundy Rd is a 4-star property offering an outdoor pool, a jacuzzi and a spa, with massage available. A gymnasium and aerobics cover exercise, while horse riding and a nearby beach widen the options. Rooms have air conditioning, fireplaces and kitchen facilities, and family rooms are offered. It suits families and groups who want space, cooking facilities and a pool to come back to.
See Bella Villa Messina
The shortlist side by side
| Hotel | Class | Parking | Breakfast | Pool or spa | Pets |
|---|---|---|---|---|---|
| Montage Healdsburg | ★★★★★ | Yes | Yes | Yes | Yes |
| The Madrona | ★★★★ | Yes | Yes | Yes | – |
| Hotel Healdsburg | ★★★★ | Yes | – | Yes | Yes |
| H2Hotel | ★★★★ | Yes | – | Yes | Yes |
| Honor Mansion | ★★★★ | Yes | Yes | Yes | – |
| Downtown Suites One | ★★★★ | Yes | Yes | Yes | – |
| Healdsburg Modern Cottages | ★★★★ | Yes | – | Yes | – |
| Grape Leaf Inn | ★★★★ | Yes | Yes | Yes | Yes |
| 27 North | ★★★★ | Yes | Yes | – | Yes |
| Urban Luxe Loft | ★★★★ | Yes | Yes | Yes | – |
| Two Thirty Five | ★★★★ | Yes | – | – | – |
| Bella Villa Messina | ★★★★ | Yes | Yes | Yes | – |
From each hotel's own listing on this site; a dash means it is not listed.
How to choose
For couples
The Madrona, Honor Mansion, Bella Villa Messina and Grape Leaf Inn all offer gardens, spas or massage and quiet settings for two; The Madrona scores 4.9 out of 5 from 133 reviews, while Honor Mansion and Grape Leaf Inn combine outdoor pools and picnic areas with breakfast and concierge service.
The Madrona · Honor Mansion · Bella Villa Messina · Grape Leaf Inn
For families
Montage Healdsburg, Hotel Healdsburg and H2Hotel all list family rooms, and Montage adds a kids pool and babysitting service; Urban Luxe Loft has kitchens and kitchenettes with an outdoor pool, useful for a longer family stay in town.
Montage Healdsburg · Hotel Healdsburg · H2Hotel · Urban Luxe Loft
For business
The Madrona, Hotel Healdsburg and Honor Mansion each list business centres, and The Madrona, Honor Mansion and Two Thirty Five have meeting rooms or conference space. Two Thirty Five on Healdsburg Avenue is a compact town address with restaurant, room service and lifts.
The Madrona · Hotel Healdsburg · Honor Mansion · Two Thirty Five
For town-centre access
Hotel Healdsburg, H2Hotel, 27 North, Downtown Suites One and Healdsburg Modern Cottages have addresses on Matheson St, Healdsburg Avenue, North St and Foss Street, putting guests within walking distance of the plaza — though each hotel's data alone should guide your pick.
Hotel Healdsburg · H2Hotel · 27 North · Downtown Suites One · Healdsburg Modern Cottages
Where to stay in Healdsburg
Grove Street
Honor Mansion sits on Grove Street just away from the plaza, a 4-star property rated 4.7 out of 5 by 89 guests, listing a garden, outdoor pool, spa, tennis court and breakfast — a quieter base for exploring town on foot.
Our picks here: Honor Mansion
Westside Road
The Madrona stands on Westside Road, out among the vines rather than in the centre, with a 4.9 out of 5 rating from 133 reviews. Its listed facilities include a restaurant, outdoor pool, fitness centre, garden and terrace for a wine-country stay away from the bustle.
Our picks here: The Madrona
Questions, answered
Which Healdsburg hotels are best rated?
The Madrona holds the highest guest rating on this list at 4.9 out of 5 from 133 reviews, followed by Honor Mansion at 4.7 from 89. Montage Healdsburg and Hotel Healdsburg each score 4.6, with 409 and 306 reviews respectively.
Is there a 5-star hotel in Healdsburg?
Yes — Montage Healdsburg on Montage Way is the only 5-star property on this list, rated 4.6 out of 5 from 409 reviews. Its facilities include a fitness centre, kids pool, Jacuzzi, spa treatments and bike rental.
Which hotels have outdoor pools?
The Madrona, Hotel Healdsburg, H2Hotel, Honor Mansion, Downtown Suites One, Healdsburg Modern Cottages, Grape Leaf Inn, Urban Luxe Loft and Bella Villa Messina all list an outdoor pool. Montage Healdsburg lists a kids pool alongside its fitness centre.
Can I bring a dog?
Hotel Healdsburg, H2Hotel, Grape Leaf Inn and 27 North list pets as allowed. Other properties on this list do not state a pet policy in their data, so confirm directly before booking.
Do the hotels have parking?
Most do: The Madrona, Hotel Healdsburg, Honor Mansion, Downtown Suites One, Healdsburg Modern Cottages, Grape Leaf Inn, 27 North, Urban Luxe Loft, Two Thirty Five and Bella Villa Messina all list free or on-site parking. H2Hotel lists valet parking.
Which hotels suit a business trip?
The Madrona, Hotel Healdsburg and Honor Mansion each list a business centre, and The Madrona, Honor Mansion and Two Thirty Five have meeting or conference space. All four-star properties here list Wi-Fi, so working from the room is straightforward.
Are there hotels with a spa?
H2Hotel, Honor Mansion, Grape Leaf Inn and Bella Villa Messina list spa facilities, and Montage Healdsburg, Hotel Healdsburg, Grape Leaf Inn and Bella Villa Messina list massage among their services.