Healdsburg Holiday Rentals

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Check prices for these dates

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Holiday Rentals in Healdsburg

Fridge, microwave, oven, stovetop
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Holiday Home in Healdsburg

10.0 out of 10, Exceptional, (66)
"This place was beautiful and we had such a lovely stay. Would recommend and also stay here again! Hosts were communicative and Andy at the property’s winery (Limerick) was an absolute gem! 🥹"
United States
Alex D.
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
View from property
Clear Lake Cottages & Marina

Aparthotel in Clearlake

2.5 star property
9.0 out of 10, Wonderful, (326)
"Great stay!"
United States
Andrey and Irina
The price is HK$1,165
HK$1,298 total
includes taxes & fees
31 Dec - 1 Jan 2026
Clear Lake Cottages & Marina
Interior
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Cabin in Bodega Bay

9.8 out of 10, Exceptional, (466)
"View was amazing!"
United States
Liz T.
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Dining
Panoramic Ocean View--3 Min Walk To Beach

Cottage in Dillon Beach

9.6 out of 10, Exceptional, (331)
"Adorable house with a perfect location! Loved the short walk to the beach and comfortable amenities. "
United States
Sarah K.
Panoramic Ocean View--3 Min Walk To Beach
Outdoor pool, a heated pool
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Holiday Home in Glen Ellen

9.8 out of 10, Exceptional, (92)
"Fabulous location perched on the mountaintop. Home is modern and clean and has everything we needed to cook and enjoy our stay. Could not have been better! "
United States
Courtney S.
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Smart TV, fireplace, DVD player, books
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

Cottage in The Sea Ranch

10.0 out of 10, Exceptional, (404)
"Wonderful adventure,"
United States
Susan K.
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Outdoor spa tub
Oceanfront - Hot Tub - Newly Remodeled Cottage

Cottage in Bodega Bay

9.8 out of 10, Exceptional, (403)
"Great location and amenities here. Easy to get to local attractions we wanted to do. I'd stay here again."
United States
Tom B.
Oceanfront - Hot Tub - Newly Remodeled Cottage
Terrace/patio
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Cottage in Monte Rio

9.8 out of 10, Exceptional, (351)
"Lovely, comfortable getaway!"
United States
William H.
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Outdoor dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Holiday Home in Kenwood

10.0 out of 10, Exceptional, (243)
"Absolutely beautiful and fun getaway with family and friends. We can't wait to come back next year. "
United States
Judy W.
The price is HK$12,456
HK$18,916 total
includes taxes & fees
29 Dec - 30 Dec
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining
Casa Bella Estate in Wine Country w/ New Pool!

Holiday Home in Kenwood

9.6 out of 10, Exceptional, (136)
"Lovely property. Pool was perfect for families with small children. Outdoor amenities are first rate. Comfortable bedding, well-equipped kitchen. Perfect setting for a large family gathering."
United States
Nita R.
Casa Bella Estate in Wine Country w/ New Pool!
TV
Bright, quiet home with amazing ocean/bay view, private hot tub & beach access

Holiday Home in Bodega Bay

8.6 out of 10, Excellent, (59)
"Blue Horizon is a clean, comfortable place to stay for a family vacation. The dining room and living room have a great view of the ocean, and you can walk to the beach (less than a half-mile walk)."
United States
Susan H.
Bright, quiet home with amazing ocean/bay view, private hot tub & beach access
Interior
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Holiday Home in St Helena

10.0 out of 10, Exceptional, (252)
"Wonderful home, perfect place for a family of all ages! "
United States
Anonymous traveller
The price is HK$12,846
HK$16,540 total
includes taxes & fees
21 Dec - 22 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Outdoor dining
The Tiny Tipsy Turtle

Cabin in Guerneville

2.0 star property
10.0 out of 10, Exceptional, (40)
"Great location to walk to town!"
United States
Brenda R.
The price is HK$763
HK$1,524 total
includes taxes & fees
2 Dec - 3 Dec
The Tiny Tipsy Turtle
Front of property
The Ranch at Lake Sonoma

Camping in Geyserville

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
United States
Tamara
The price is HK$462
HK$527 total
includes taxes & fees
1 Dec - 2 Dec
The Ranch at Lake Sonoma
Interior
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Holiday Home in Bodega Bay

9.4 out of 10, Exceptional, (219)
"Great location "
United States
jerry d.
The price is HK$3,331
HK$6,069 total
includes taxes & fees
9 Dec - 10 Dec
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
On the beach
'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK

Holiday Home in Dillon Beach

9.6 out of 10, Exceptional, (155)
"Great location near Dillon Beach with gorgeous views!"
United States
Kathryn D.
'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK
Interior
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Holiday Home in Old Town Bodega Bay

9.4 out of 10, Exceptional, (352)
"Loved this property and the views. "
United States
anne
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Beach nearby, sun-loungers, beach towels
Bodega Bay on the Edge of Pacific Ocean

Holiday Home in Bodega Bay

9.6 out of 10, Exceptional, (164)
"Check-in was very easy, and our stay was comfortable. The house had everything we needed for our short 2-night stay. We had access to a beach and a trail within walking distance. It was amazing! "
United States
Ruth Y.
Bodega Bay on the Edge of Pacific Ocean
Dining
Clean & Spacious-Walk to the Fairmont, great restaurants, coffee shops and wine

Holiday Home in Boyes Hot Springs

4.0 star property
9.8 out of 10, Exceptional, (41)
"14 of us came here for my friend's bachellorette weekend. It was tight but perfect. We had good food, good wine, good hiking, and just a great weekend together."
United States
Martha L.
The price is HK$2,336
HK$4,897 total
includes taxes & fees
8 Dec - 9 Dec
Clean & Spacious-Walk to the Fairmont, great restaurants, coffee shops and wine
Outdoor pool
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

Holiday Home in Boyes Hot Springs

9.8 out of 10, Exceptional, (118)
"Incredibly responsive and beautiful backyard! "
United States
Tina & Danny Mathan
The price is HK$6,306
HK$10,909 total
includes taxes & fees
1 Dec - 2 Dec
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA
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

Best Western Dry Creek Inn

Best Western Dry Creek Inn

10/10 Excellent
"Clean room, close/by dining"
Marie 1-night trip
Posted 4 days ago
Best Western Dry Creek Inn

Find out more about Healdsburg

Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:

  • View our selection of featured holiday rentals in Healdsburg
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Look no further and take a look at our great range of rental properties in Healdsburg!

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 wineries and top-notch restaurants.

What are some of the best holiday rentals that Healdsburg has to offer?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Healdsburg is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Healdsburg?

Expedia has 138 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.