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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Healdsburg holiday rentals

Villa, 6 Bedrooms | Pool | Outdoor pool
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
Geyserville
The price is 14.623.538 ₫
33.417.112 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
Front of property
The Ranch at Lake Sonoma

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
10.0 out of 10, Exceptional, (2)
"Nice camping spot "
United States
Evelyn
The price is 1.563.170 ₫
1.782.014 ₫ total
includes taxes & fees
27 Dec - 28 Dec
The Ranch at Lake Sonoma
Property grounds
Backyard Garden Oasis

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is 4.675.037 ₫
5.212.673 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Backyard Garden Oasis
View from property
Clear Lake Cottages & Marina

Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.0 out of 10, Wonderful, (327)
"Great stay!"
United States
Andrey and Irina
The price is 4.184.244 ₫
4.665.432 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Clear Lake Cottages & Marina
Meeting facility
Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
United States
Belwadi
The price is 4.239.508 ₫
4.727.052 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Mandala Springs Wellness Retreat Center
House (2 Bedrooms) | Interior
Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
The price is 2.842.128 ₫
6.046.890 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Room, 1 Bedroom | Terrace/patio
Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
The price is 3.767.135 ₫
7.428.217 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Rouge Cobb Mountain Hotel - Cabin 1
House, 3 Bedrooms | Property grounds
Lakeside Retreat With Private Boat Ramp 3 Bedroom Home by RedAwning

Lakeside Retreat With Private Boat Ramp 3 Bedroom Home by RedAwning

Lakeside Retreat With Private Boat Ramp 3 Bedroom Home by RedAwning
3.0 star property
Clearlake
The price is 4.022.927 ₫
14.228.009 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Lakeside Retreat With Private Boat Ramp 3 Bedroom Home by RedAwning
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is 4.500.036 ₫
11.359.301 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Russian River Retreat! Woodsy Guerneville Bungalow
Room, 1 Bedroom | Outdoor dining
Rouge Cobb Mountain Hotel - Cabin 2

Rouge Cobb Mountain Hotel - Cabin 2

Rouge Cobb Mountain Hotel - Cabin 2
2.0 star property
Cobb
The price is 3.568.186 ₫
7.142.162 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
Rouge Cobb Mountain Hotel - Cabin 2
Studio | Exterior
Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3
2.0 star property
Cobb
The price is 3.710.293 ₫
7.346.375 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
Rouge Cobb Mountain Hotel - Cabin 3
Room, 2 Bedrooms | Terrace/patio
Rouge Cobb Mountain Hotel - Cabin 5

Rouge Cobb Mountain Hotel - Cabin 5

Rouge Cobb Mountain Hotel - Cabin 5
2.0 star property
Cobb
The price is 5.017.672 ₫
9.226.916 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
Rouge Cobb Mountain Hotel - Cabin 5
Room, 1 Bedroom | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Rouge Cobb Mountain Hotel - Cabin 4

Rouge Cobb Mountain Hotel - Cabin 4

Rouge Cobb Mountain Hotel - Cabin 4
2.0 star property
Cobb
The price is 4.562.931 ₫
8.572.963 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
Rouge Cobb Mountain Hotel - Cabin 4
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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Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"Terrific staff and very nice rooms. Felt clean, maintained, and elevated. Balcony and fireplace both nice options. Staff were beyond excellent. Elliot and Brook checked us in and were really great. Brook text to check on us and Elliot helped us with check in and later food/drinks. Great locations. "
Reid 1-night trip
Posted 3 days ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the top-notch restaurants and wineries.

How many holiday rentals are there in Healdsburg?

Expedia has 140 holiday rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Healdsburg Ridge Open Space Preserve, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.