Search Vacation Homes in Healdsburg

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 195 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
10.0 out of 10, Exceptional, (59)
"Beautiful home and very well appointed. The neighborhood was quiet and easy access walking to local shops. Lovely trees for tranquility in the back yard."
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, (90)
"Fantastic home on the river with excellent private dock with easy access. Perfect spot as there are no homes across the river and it’s a short paddle to town and Johnson’s beach. We saw lots of birds, jumping fish, and deer. House has lots of comfortable outdoor seating, four kayaks and tons of floaties. Be sure to bring your own deck chairs for sitting by the river. Upgraded, remodeled home with all essential spices and great cookware. Charlie was an excellent host welcoming us with red...
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
8.0 out of 10, Very Good, (7)
"This funky, spacious property was just perfect for two couples for a cycling holiday. We loved hanging out in all the social spaces, inside and out. The river was great to cool off in. The routes inland, south in the forests, and west to the coast are excellent for road biking. The gardens were beautiful & the fencing made parking & setting up the bikes secure. We appreciated the hot tub after one misty ride. We had no problems with rodents, since we kept all our food in the fridge. We had a...
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
Save an average of 15% on thousands of hotels when you're signed in
Beautiful 4 bedroom home w/ luxurious furnishings
9.4 out of 10, Exceptional, (15)
"Very nice spacious house. Quiet neighborhood. Just what we all needed. Beds are SUPER comfy!"
Beautiful 4 bedroom home w/ luxurious furnishings
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (79)
"Our family had a wedding to attend in the area and the accommodations were perfect for us! Close to everything. We appreciated having some staples available too (coffee!). Would stay there again for sure!"
Cottage home near the Russian River; county parks; numerous wineries
Guerneville Getaway: Craftsman Retreat! Fun! GameRoom! Hot Tub! Near Wineries
9.4 out of 10, Exceptional, (3)
"A lovely, well-appointed property with almost everything you need. We had a relaxing stay and the house is in a quiet residential neighborhood. Downtown Guerneville is a quick drive away."
Guerneville Getaway: Craftsman Retreat! Fun! GameRoom! Hot Tub! Near Wineries
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
9.8 out of 10, Exceptional, (11)
"Cute little river house. Comfortable bed, newly remodeled, clean interior. Has most amenities for cooking (bring your own seasonings). Hot tub works well but turn it up when you arrive so it's hot when you want to use it. Tight driveway, don't recommend a full size truck. Definitely would stay here again."
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
7.6 out of 10, Good, (9)
"We loved the location as it was close to everywhere we planned on visiting and it was nice to have a location with a hot tub to enjoy. The pillows were amazing! The problem with this location is that it is right across from a vineyard and it was harvest season and we got little to no sleep due to the ongoing activity. Workers were driving up and down the road with tractors and in the vineyard there were harvesters with spotlights so it was very busy. The cabin furniture could use some...
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
9.6 out of 10, Exceptional, (12)
"We enjoyed the house very much! Backyard was great for cocktails and relaxing. The host was very responsive. Clean and well kept."
The price is SAR 2,382
SAR 4,663 total
includes taxes & fees
4 Jum. II - 5 Jum. II
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Windsor Wine Country Vacation Home
9.6 out of 10, Exceptional, (87)
"Property looked new, very clean, kitchen fully equipped, enough coffe, tea sugar for the family though we brought our own tea and coffee. Enough toiletries, towels in all bathrooms, good beds. I would highly recommend this property."
Windsor Wine Country Vacation Home
B - Wine Country Getaway
9.6 out of 10, Exceptional, (10)
"We were looking for a place to stay for a wine weekend, and this place was perfect. Cozy and great location, easy in/out."
B - Wine Country Getaway
Wood Chalet - Dazzling, bright & Upscale! Huge windows/ HotTub/ Near Wineries
9.8 out of 10, Exceptional, (18)
"this house was perfect for adult relatives to stay together because each of the three bedrooms has their own bathroom. the kitchen and common living room are open and modern with a vaulted ceiling and a massive window facing a forest of redwood trees. We enjoyed the very large and super clean hot tub. Everything was modern and clean. There are lots of steps from the road to the entrance, which was fine for us, but might be a challenge for some people."
Wood Chalet - Dazzling, bright & Upscale! Huge windows/ HotTub/ Near Wineries
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
10.0 out of 10, Exceptional, (98)
"Six of us get together every year and we all have a connection to Healdsburg. it was great being close to town but not in the middle of town. Thank you for sharing your home. We had a great time. Kathy Cross"
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (278)
"We were so impressed the first time that we stayed here, we had to come back again. The house is beautiful and perfect for two couples. And the view from the deck...amazing!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks
9.6 out of 10, Exceptional, (80)
"Nice quiet neighborhood with plenty of room for everyone."
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks
Wine country home base with dog-friendly fenced yard & alfresco patio
8.0 out of 10, Very Good, (5)
"Pros:This house was convenient to vineyards and does have a small back yard that was fine for our needs. Cons: Carpet needs cleaning, table in back is missing a top. Biggest issue was the heat. Temperature was in the upper 80s and there is no A/C. House was unbearably hot in the afternoons and evening especially upstairs where bedrooms are located. Vacasa was not helpful."
Wine country home base with dog-friendly fenced yard & alfresco patio
Private Vineyard Haven--walk to the HBG Square!
9.8 out of 10, Exceptional, (38)
"Fantastic location! Super clean, easy check in process. Had Evette needed and the house just truly completed and enhanced our visit to wine country!"
Private Vineyard Haven--walk to the HBG Square!
Hidden Oasis ~ a Private Luxury Home in Healdsburg
10.0 out of 10, Exceptional, (11)
"Property was a terrific place to use as a base to explore wine country. Outdoor space is great! Would definitely recommend it."
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Walk to Russian River - Casa del Rio - Unit B
9.8 out of 10, Exceptional, (6)
"The property is nicely done. People are very friendly that manager it. We enjoyed our stay ."
Walk to Russian River - Casa del Rio - Unit B
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
8.8 out of 10, Excellent, (3)
"Really nice private area on the property - for the review about the wifi - it worked wonderful - was gone during the day but relaxing and good vibe when I was there. Nice outside area as well."
The price is SAR 559
SAR 705 total
includes taxes & fees
4 Jum. II - 5 Jum. II
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
Don't see what you're looking for?
See all available properties in 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.

Other property types in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (278)
"We were so impressed the first time that we stayed here, we had to come back again. The house is beautiful and perfect for two couples. And the view from the deck...amazing!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
10.0 out of 10, Exceptional, (263)
"Our favorite place to stay for R&R. Private and peaceful, surrounded by vineyards. Close to town, but away from it all. Love it. Thanks again as always, Wayne and Pauline!"
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (148)
"We love staying at this property in Dry Creek! It is so clean and has everything you'd want.. the location is perfect, right in the middle of everything Dry Creek and Healdsburg."
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
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.

Recent reviews of Healdsburg hotels
Expedia verified reviews