Hotels logo

Hotels with a Pool in Healdsburg

October 2026
November 2026

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Hotels with a Pool in Healdsburg

A swimming pool with lounge chairs and a covered seating area, surrounded by a white building with arches and a flagpole.
A kitchen with a wooden table, two stools, a large mirror, and white cabinetry.
A courtyard with a stone balustrade and arches covered in ivy.
A kitchen with a white countertop, wooden stools, and a large mirror above the sink.

1. Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
Healdsburg
  • Outdoor pool
  • Pool loungers
$135
$157 total
includes taxes & fees
Oct 25 - Oct 26
Dry Creek Inn MOD Collection by Sonesta
A swimming pool with lounge chairs and umbrellas, surrounded by multi-story buildings with balconies.
A hotel sign with illuminated text and a leaf design, surrounded by outdoor seating and a covered area.
An outdoor seating area with a fire feature, cushioned seating, and umbrellas.
A modern cafe with wooden chairs and tables, large windows, and a view of the outdoors.

2. Hotel Trio Healdsburg

Hotel Trio Healdsburg
Healdsburg
  • Outdoor pool
$149
$194 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Trio Healdsburg
A swimming pool with lounge chairs, a pergola, and a gazebo.
A spacious indoor area with multiple round tables and chairs, large windows with curtains, and a stone wall.
A spacious room with a large window, a chandelier, and a balcony with a balustrade.
A bedroom with a fireplace, a sofa, a bed, a desk, and a large window with blinds.

3. The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
Healdsburg
  • Outdoor pool
  • Pool loungers
  • 2 hot tubs
$159
$185 total
includes taxes & fees
Oct 4 - Oct 5
The Lodge at Healdsburg, Tapestry Collection by Hilton
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and balconies.
A covered outdoor seating area with a sofa and two round tables, surrounded by greenery and a stone wall.
A spacious hotel lobby with a seating area, a dining section, and a large window providing natural light.
A hotel with a prominent entrance, a well-lit facade, and a landscaped front garden.

4. Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country
Windsor
  • Outdoor pool
  • Hot tub
$147
$168 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Windsor - Sonoma Wine Country
A poolside area with a tiled deck, a pool with a depth marker, and outdoor seating with chairs and tables.
A modern lounge area with a wooden ceiling, a large window, and a seating arrangement including sofas and ottomans.
A modern outdoor seating area with three wooden benches and a central table, set against a backdrop of vertical wooden slats and a cityscape view.
A modern building with multiple balconies and a staircase leading to an upper level.

5. Harmon Guest House

Harmon Guest House
Healdsburg
  • Outdoor pool
  • Full-service spa
$359
$458 total
includes taxes & fees
Oct 25 - Oct 26
Harmon Guest House
A swimming pool area with lounge chairs and a no diving sign.
A hotel room with a bed, a TV, a desk, a chair, a table, and a dining area with a table set for two.
An outdoor patio area with round tables and chairs, umbrellas, and potted plants.
A modern kitchen with dark cabinets, stainless steel appliances, a microwave, and a dishwasher.

6. Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG
Windsor
  • Indoor pool
$135
$154 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Windsor Wine Country by IHG
A pool area with lounge chairs, umbrellas, and a clear view of the surrounding forest.
A living room with a brown leather sofa, a wooden coffee table with a candle and a plant, a window with blinds, and a colorful abstract painting on the wall.
A hotel room with a large bed, a desk, a chair, a TV, and a bathroom.
A modern living room with a brown leather sofa, a coffee table with a bottle and glasses, and a large abstract painting on the wall.

7. Fairview Inn and Suites

Fairview Inn and Suites
Healdsburg
  • Outdoor pool
  • Pool loungers
  • Hot tub
$146
$169 total
includes taxes & fees
Sep 28 - Sep 29
Fairview Inn and Suites
A swimming pool area with lounge chairs, a glass wall with plants, and a modern interior design.
A modern lobby with a central reception desk, a seating area with a patterned sofa, and a bookshelf filled with books.
A modern interior with a bar area, wooden ceiling, and a wall decorated with sunflowers.
A bar with a sign indicating it's open, patio seating, and a Spoonbar sign.

8. H2Hotel

H2Hotel
Healdsburg
  • Outdoor pool
  • Pool loungers
  • Full-service spa
$332
$427 total
includes taxes & fees
Sep 27 - Sep 28
H2Hotel
A swimming pool with a fence, lounge chairs, and a building with columns.
A multi-story building with a central entrance, large windows, and a covered walkway.
A modern kitchen with a breakfast bar, a coffee station, and a sign indicating breakfast service.
A large building with a central fountain and flower planters.

9. Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Windsor
  • Outdoor pool
  • Hot tub
$115
$131 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
A swimming pool with a curved edge, surrounded by a deck with lounge chairs and a covered seating area.
A row of cabins with outdoor seating areas, surrounded by a well-maintained garden and a forested backdrop.
A courtyard with a fire pit surrounded by blue chairs, a stone pathway, and a lawn leading to a house.
A bedroom with a wooden dresser, a bed, a nightstand, a framed picture, a round mirror, and a bathroom visible through an open door.

10. Cottages on River Road

Cottages on River Road
Guerneville
  • Outdoor pool
$102
$122 total
includes taxes & fees
Oct 1 - Oct 2
Cottages on River Road
A poolside area with lounge chairs, a flamingo float, and a wooden fence in the background.
A historic building with a prominent arched entrance, a sign reading "Cambria Inn," and a well-maintained garden with red flowers and pathway lighting.
A grand entrance with a white staircase, a chandelier, and a stained glass door with a floral design.
A spacious dining area with wooden flooring, white walls, and a chandelier. There are multiple dining tables and chairs arranged for guests.

11. Camellia Inn

Camellia Inn
Healdsburg
  • Pool loungers
  • Full-service spa
$247
$287 total
includes taxes & fees
Oct 25 - Oct 26
Camellia Inn
A swimming pool with a metal safety rail, two red lounge chairs, and a wooden fence.
A two-story house with a gabled roof, a front entrance, and a driveway leading to a gated parking area.
A room with a large window, a round table, and two blue armchairs.
A dining area with a table set for two, a window with a view of a deck and trees, and two chairs with cushions.

12. Grape Leaf Inn

Grape Leaf Inn
Healdsburg
  • Outdoor pool
  • Pool loungers
$301
$349 total
includes taxes & fees
Sep 27 - Sep 28
Grape Leaf Inn
A poolside area with lounge chairs, a table, and a potted plant.
A modern hotel with a central courtyard, large windows, and a well-maintained lawn.
A dining area with wicker chairs and tables, large windows with curtains, and a chandelier.
A swimming pool with lounge chairs and a building with ivy-covered walls.

13. Hotel Healdsburg

Hotel Healdsburg
Healdsburg
  • Outdoor pool
  • Hot tub
$499
$632 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Healdsburg
A person floating in a pool with a colorful unicorn float, a building with balconies, and a clear blue sky.
A loft-style room with a large window, a bench, two armchairs, and a small table.
A bedroom with a large bed, a desk, a chair, a TV, and a ceiling fan.
A tiered stone fountain in an outdoor seating area with wicker furniture and potted plants.

14. Geyserville Inn

Geyserville Inn
Geyserville
  • Outdoor pool
  • Pool loungers
  • Hot tub
$179
$218 total
includes taxes & fees
Sep 28 - Sep 29
Geyserville Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.
A Wine Country Inn & Suites with a large entrance, American flags, and well-lit exterior.
A hotel room with two beds, a red armchair, a large window with a view, and abstract wall art.
An outdoor patio area with multiple tables and chairs, string lights, and a covered section with a pergola.

15. Best Western Plus Wine Country Inn & Suites

Best Western Plus Wine Country Inn & Suites
Santa Rosa
  • Outdoor pool
  • Pool loungers
$124
$144 total
includes taxes & fees
Sep 27 - Sep 28
Best Western Plus Wine Country Inn & Suites
A hotel pool area with a hot tub, lounge chairs, and a building in the background.
A modern hotel lobby with a large seating area, a wooden reception desk, and large windows offering a view of the outdoors.
A bar area with a wooden counter, bar stools, and a wine display.
A modern kitchen with a large island, bar stools, and a view of a pool.

16. The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
Santa Rosa
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$101
$118 total
includes taxes & fees
Oct 25 - Oct 26
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
A swimming pool with lounge chairs and a sunshade, surrounded by large windows.
A spacious lobby with a large fireplace, a sofa, a coffee table, and a bookshelf.
An outdoor patio with stone walls, wooden pergola, and multiple tables and chairs under beige umbrellas.
A breakfast bar with various food items and a waffle batter station.

17. Hilton Garden Inn Sonoma County Airport

Hilton Garden Inn Sonoma County Airport
Santa Rosa
  • Indoor pool
$131
$150 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Garden Inn Sonoma County Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped area and buildings.
A modern outdoor patio with a wooden ceiling, a dining area with chairs and a table, and a view of vineyards in the background.
A rooftop terrace with wicker chairs and a railing overlooking a vineyard.
A restaurant interior with a long wooden counter, hanging pendant lights, and a view of the outdoors.

18. Appellation Healdsburg

Appellation Healdsburg
Healdsburg
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • 2 hot tubs
$353
$480 total
includes taxes & fees
Oct 22 - Oct 23
Appellation Healdsburg
A poolside area with a fire pit, outdoor seating, and umbrellas.
A dining room with a piano, a table set for six, and a view of greenery outside.
A covered outdoor seating area with a white railing, surrounded by lush greenery and palm trees.
A modern bathroom with a freestanding bathtub, a large mirror, and a marble countertop.

19. The Madrona

The Madrona
Healdsburg
  • Outdoor pool
  • Pool loungers
$446
$551 total
includes taxes & fees
Oct 7 - Oct 8
The Madrona
A Hampton Inn & Suites with a pool area, outdoor seating, and a clear blue sky.
A modern breakfast area with a central table, coffee machines, and a sign that reads "Happy Breakfast Starts Here".
A modern waiting area with a blue cushioned bench, wooden storage compartments, and artwork on the walls.
A Hampton Inn & Suites hotel with a modern design, featuring a covered entrance and a well-lit facade.

20. Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Hampton Inn & Suites Santa Rosa Sonoma Wine Country
Santa Rosa
  • Outdoor pool
$142
$164 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn & Suites Santa Rosa Sonoma Wine Country
See more properties

Discover your perfect hotel with a pool in Healdsburg

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and free breakfast in Healdsburg

A hotel with a modern design, featuring a prominent entrance, multiple balconies, and a well-maintained outdoor area with trees and seating.
An outdoor seating area with a fire feature, cushioned seating, and umbrellas.
A modern cafe with wooden chairs and tables, large windows, and a view of the outdoors.
A hotel sign with the name "HOTEL TRIO" and a logo of three leaves.

Hotel Trio Healdsburg

Hotel Trio Healdsburg
Healdsburg
$149
$194 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Trio Healdsburg
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and balconies.
A covered outdoor seating area with a sofa and two round tables, surrounded by greenery and a stone wall.
A spacious hotel lobby with a seating area, a dining section, and a large window providing natural light.
A hotel with a prominent entrance, a well-lit facade, and a landscaped front garden.

Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country
Windsor
$147
$168 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Windsor - Sonoma Wine Country
A dining area with wicker chairs and tables, large windows with curtains, and a chandelier.
A poolside area with lounge chairs, a table, and a potted plant.
A swimming pool with lounge chairs and a building with ivy-covered walls.
A pool area with lounge chairs and umbrellas, surrounded by trees and greenery.

Hotel Healdsburg

Hotel Healdsburg
Healdsburg
$499
$632 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Healdsburg
A spacious room with a large window, a chandelier, and a balcony with a balustrade.
A spacious indoor area with multiple round tables and chairs, large windows with curtains, and a stone wall.
An outdoor patio area with seating, a fire feature, and a sign reading 'Piazza.'
A bedroom with a fireplace, a sofa, a bed, a desk, and a large window with blinds.

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
Healdsburg
$159
$185 total
includes taxes & fees
Oct 4 - Oct 5
The Lodge at Healdsburg, Tapestry Collection by Hilton
A multi-story hotel with a central archway, balconies, and a parking area.
A kitchen with a wooden table, two stools, a large mirror, and white cabinetry.
A courtyard with a stone balustrade and arches covered in ivy.
A kitchen with a white countertop, wooden stools, and a large mirror above the sink.

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
Healdsburg
$135
$157 total
includes taxes & fees
Oct 25 - Oct 26
Dry Creek Inn MOD Collection by Sonesta
A poolside area with lounge chairs and a pink flamingo float.
A spacious dining area with wooden flooring, white walls, and a chandelier. There are multiple dining tables and chairs arranged for guests.
A traditional living room with a fireplace, leather sofas, a coffee table, and a bookshelf.
A grand entrance with a white staircase, a chandelier, and a stained glass door with a floral design.

Camellia Inn

Camellia Inn
Healdsburg
$247
$287 total
includes taxes & fees
Oct 25 - Oct 26
Camellia Inn
A modern kitchen with dark cabinets, stainless steel appliances, a microwave, and a dishwasher.
An outdoor patio area with round tables and chairs, umbrellas, and potted plants.
A conference room with multiple tables and chairs, a carpeted floor, and ceiling-mounted lighting fixtures.
A swimming pool area with lounge chairs and a no diving sign.

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG
Windsor
$135
$154 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Windsor Wine Country by IHG
A multi-story building with a central entrance, large windows, and a covered walkway.
A modern kitchen with a breakfast bar, a coffee station, and a sign indicating breakfast service.
A hotel room with a desk, chair, sofa, and a standing lamp.
A hotel room with two beds, a desk, a chair, a lamp, and a large window.

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Windsor
$115
$131 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
An aerial view of a resort with a large swimming pool surrounded by sun loungers and a vineyard.
A modern bar area with a large fireplace, seating, and a view of the outdoors.
An outdoor dining area with tables and chairs under trees, string lights, and a view of the landscape.
A vineyard with rows of grapevines, a modern building with a patio area, and a sunset in the background.

Montage Healdsburg

Montage Healdsburg
Healdsburg
$850
$1,077 total
includes taxes & fees
Oct 25 - Oct 26
Montage Healdsburg
A large, historic house with a prominent corner turret and a well-maintained garden.
A poolside area with a fire pit, outdoor seating, and umbrellas.
A dining room with a piano, a table set for six, and a view of greenery outside.
A hotel room with a large bed, a fireplace, a sofa, a dining table, and a view of the outdoors.

The Madrona

The Madrona
Healdsburg
$446
$551 total
includes taxes & fees
Oct 7 - Oct 8
The Madrona
View all properties

Hotels with pools and hot tubs in Healdsburg

A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and balconies.
A covered outdoor seating area with a sofa and two round tables, surrounded by greenery and a stone wall.
A spacious hotel lobby with a seating area, a dining section, and a large window providing natural light.
A hotel with a prominent entrance, a well-lit facade, and a landscaped front garden.

Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country
Windsor
$147
$168 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Windsor - Sonoma Wine Country
A spacious room with a large window, a chandelier, and a balcony with a balustrade.
A spacious indoor area with multiple round tables and chairs, large windows with curtains, and a stone wall.
An outdoor patio area with seating, a fire feature, and a sign reading 'Piazza.'
A bedroom with a fireplace, a sofa, a bed, a desk, and a large window with blinds.

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
Healdsburg
$159
$185 total
includes taxes & fees
Oct 4 - Oct 5
The Lodge at Healdsburg, Tapestry Collection by Hilton
A dining area with wicker chairs and tables, large windows with curtains, and a chandelier.
A poolside area with lounge chairs, a table, and a potted plant.
A swimming pool with lounge chairs and a building with ivy-covered walls.
A pool area with lounge chairs and umbrellas, surrounded by trees and greenery.

Hotel Healdsburg

Hotel Healdsburg
Healdsburg
$499
$632 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Healdsburg
A multi-story building with a central entrance, large windows, and a covered walkway.
A modern kitchen with a breakfast bar, a coffee station, and a sign indicating breakfast service.
A hotel room with a desk, chair, sofa, and a standing lamp.
A hotel room with two beds, a desk, a chair, a lamp, and a large window.

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Windsor
$115
$131 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
A restaurant interior with a long wooden counter, hanging pendant lights, and a view of the outdoors.
A vineyard with rows of grapevines, a building with the number 45, and outdoor seating areas.
A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped area and buildings.
A modern outdoor patio with a wooden ceiling, a dining area with chairs and a table, and a view of vineyards in the background.

Appellation Healdsburg

Appellation Healdsburg
Healdsburg
$353
$480 total
includes taxes & fees
Oct 22 - Oct 23
Appellation Healdsburg
A swimming pool with lounge chairs and umbrellas, surrounded by modern buildings.
A modern living room with a fireplace, wooden ceiling, and large windows.
A balcony with a pool view, outdoor seating, and a railing.
A person holding a shopping bag with 'BON TON STUDIO' text, standing in a room with woven wall decorations.

Duchamp Healdsburg

Duchamp Healdsburg
Healdsburg
$500
$581 total
includes taxes & fees
Sep 27 - Sep 28
Duchamp Healdsburg
An aerial view of a resort with a large swimming pool surrounded by sun loungers and a vineyard.
A modern bar area with a large fireplace, seating, and a view of the outdoors.
An outdoor dining area with tables and chairs under trees, string lights, and a view of the landscape.
A vineyard with rows of grapevines, a modern building with a patio area, and a sunset in the background.

Montage Healdsburg

Montage Healdsburg
Healdsburg
$850
$1,077 total
includes taxes & fees
Oct 25 - Oct 26
Montage Healdsburg
A modern living room with a brown leather sofa, a coffee table with a bottle and glasses, and a large abstract painting on the wall.
A living room with a brown leather sofa, a wooden coffee table with a candle and a plant, a window with blinds, and a colorful abstract painting on the wall.
A pool area with lounge chairs, umbrellas, and a clear view of the surrounding forest.
A hotel room with a large bed, a desk, a chair, a TV, and a bathroom.

Fairview Inn and Suites

Fairview Inn and Suites
Healdsburg
$146
$169 total
includes taxes & fees
Sep 28 - Sep 29
Fairview Inn and Suites
A fountain surrounded by a brick pathway, with a building featuring a tiled roof and ivy-covered walls in the background.
A spacious living room with a high ceiling, wooden beams, a large window, and a view of the outdoors.
A resort with a large pool surrounded by lounge chairs and umbrellas, set in a landscaped area with buildings in the background.
A bar setting with a glass of red wine on a tiled surface.

Vinarosa Resort & Spa

Vinarosa Resort & Spa
Santa Rosa
$340
$453 total
includes taxes & fees
Oct 25 - Oct 26
Vinarosa Resort & Spa
A hotel room with a fireplace, two beds, a large TV, and a balcony with a view.
A spacious living room with a fireplace, a flat-screen TV, a comfortable sofa, a small round table, and a balcony with a view of greenery.
A loft-style room with a large window, a bench, two armchairs, and a small table.
A bedroom with a large bed, a desk, a chair, a TV, and a ceiling fan.

Geyserville Inn

Geyserville Inn
Geyserville
$179
$218 total
includes taxes & fees
Sep 28 - Sep 29
Geyserville Inn
View all properties

4-star hotels with pools in Healdsburg

A dining area with wicker chairs and tables, large windows with curtains, and a chandelier.
A poolside area with lounge chairs, a table, and a potted plant.
A swimming pool with lounge chairs and a building with ivy-covered walls.
A pool area with lounge chairs and umbrellas, surrounded by trees and greenery.

Hotel Healdsburg

Hotel Healdsburg
Healdsburg
$499
$632 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Healdsburg
A swimming pool area with lounge chairs, a glass wall with plants, and a modern interior design.
A modern lobby with a central reception desk, a seating area with a patterned sofa, and a bookshelf filled with books.
A modern interior with a bar area, wooden ceiling, and a wall decorated with sunflowers.
A bar with a sign indicating it's open, patio seating, and a Spoonbar sign.

H2Hotel

H2Hotel
Healdsburg
$332
$427 total
includes taxes & fees
Sep 27 - Sep 28
H2Hotel
A restaurant interior with a long wooden counter, hanging pendant lights, and a view of the outdoors.
A vineyard with rows of grapevines, a building with the number 45, and outdoor seating areas.
A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped area and buildings.
A modern outdoor patio with a wooden ceiling, a dining area with chairs and a table, and a view of vineyards in the background.

Appellation Healdsburg

Appellation Healdsburg
Healdsburg
$353
$480 total
includes taxes & fees
Oct 22 - Oct 23
Appellation Healdsburg
A large, historic house with a prominent corner turret and a well-maintained garden.
A poolside area with a fire pit, outdoor seating, and umbrellas.
A dining room with a piano, a table set for six, and a view of greenery outside.
A hotel room with a large bed, a fireplace, a sofa, a dining table, and a view of the outdoors.

The Madrona

The Madrona
Healdsburg
$446
$551 total
includes taxes & fees
Oct 7 - Oct 8
The Madrona
An outdoor patio with a wooden deck, two wooden chairs, a table, and a large vase.
A room with a large window, a round table, and two blue armchairs.
A bedroom with a wooden ceiling, a large bed with white bedding, a bench at the foot of the bed, and a window with a view.
A dining room with a piano, a long table set for a meal, and a staircase in the background.

Grape Leaf Inn

Grape Leaf Inn
Healdsburg
$301
$349 total
includes taxes & fees
Sep 27 - Sep 28
Grape Leaf Inn
A fountain surrounded by a brick pathway, with a building featuring a tiled roof and ivy-covered walls in the background.
A spacious living room with a high ceiling, wooden beams, a large window, and a view of the outdoors.
A resort with a large pool surrounded by lounge chairs and umbrellas, set in a landscaped area with buildings in the background.
A bar setting with a glass of red wine on a tiled surface.

Vinarosa Resort & Spa

Vinarosa Resort & Spa
Santa Rosa
$340
$453 total
includes taxes & fees
Oct 25 - Oct 26
Vinarosa Resort & Spa
View all properties

Top landmarks in Healdsburg

Dry Creek Vineyard

9.4/10 (126 reviews)
Travelers might want a tour of Dry Creek Vineyard, just one of the places to visit, and located 4.2 mi (6.8 km) from central Healdsburg. Why not take a stroll along the riverfront and watch the sunset while you're here?
See properties

Healdsburg Plaza

9.4/10 (657 reviews)
If you're planning a bit of sightseeing during your trip, head to Healdsburg Plaza— just one of the monuments in central Healdsburg. Why not take a stroll along the riverfront and watch the sunset while you're here?
See properties

Jordan Vineyard & Winery

10.0/10 (11 reviews)
Travelers might want a tour of Jordan Vineyard & Winery, just one of the places to visit, and located 3.4 mi (5.5 km) from central Healdsburg.
See properties

Mazzocco Winery

8.6/10 (24 reviews)
Travelers might want a tour of Mazzocco Winery, just one of the places to visit, and located 3.6 mi (5.7 km) from central Healdsburg. Why not take a stroll along the riverfront and watch the sunset while you're here?
See properties

Ridge Vineyards - Lytton Springs

Travelers might want a tour of Ridge Vineyards - Lytton Springs, just one of the places to visit, and located 3.5 mi (5.6 km) from central Healdsburg.
See properties

Wilson Winery

8.6/10 (38 reviews)
Travelers might want a tour of Wilson Winery, just one of the places to visit, and located 2.6 mi (4.2 km) from central Healdsburg. Why not take a stroll along the riverfront and watch the sunset while you're here?
See properties

SingleThread Farm at Dry Creek

SingleThread Farm at Dry Creek is 3.5 mi (5.7 km) from central Healdsburg, why not stop by during your stay. If you have fun at SingleThread Farm at Dry Creek, you'll love Healdsburg Center for the Arts and Raven Performing Arts Theater, both located nearby.
See properties

Chalk Hill Estate Vineyard

8.4/10 (12 reviews)
Travelers might want a tour of Chalk Hill Estate Vineyard, just one of the places to visit, and located 6 mi (9.7 km) from central Healdsburg. Why not take a stroll along the riverfront and watch the sunset while you're here?
See properties

About the destination

Healdsburg is a walkable location known for its wineries and restaurants. Activities like biking give you a chance to enjoy the outdoors while you're in town. Nature lovers can visit Russian River and Healdsburg Ridge Open Space Preserve. There's plenty more to see, including sights like Healdsburg Plaza and Jordan Vineyard & Winery.