Holiday Homes in Healdsburg

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Featured Holiday Homes in Healdsburg

Property grounds
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
Pool
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
10.0 out of 10, Exceptional, (57)
"Beautiful quiet property surrounded by trees with sunny deck and hot tub. Great for a weekend getaway from the city to relax."
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
Fridge, microwave, oven, stovetop
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
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Fridge, microwave, oven, stovetop
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
Property grounds
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, (88)
"Could not have had a better experience"
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
A heated pool
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!
Interior
Guerneville Getaway: Craftsman Retreat! Fun! Game Room / Hot Tub! 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! Game Room / Hot Tub! Wineries!
Property grounds
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (78)
"Great property that is close to hiking and wine country. Enjoyed our stay and would recommend."
Cottage home near the Russian River; county parks; numerous wineries
Towels
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
7.6 out of 10, Good, (8)
"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
Golf
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (156)
"We had a great experience at Fitch Mountain Lookout. The home has a great view, is a short walk downhill to the river, and only a short drive to town. We most enjoyed watching the birds come to the feeders in the morning while we started our day in the hot tub!"
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Property grounds
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
Fridge, microwave, oven, stovetop
Santa Rosa Serenity: Cozy 1bd Perch Amidst Wine Country
9.4 out of 10, Exceptional, (12)
"We picked Santa Rosa because there was dog show that we wanted to attend with our dog. We stayed for 3 nights in this lovely dog friendly property. There were also people staying downstairs with their dogs who were also attending the dog show. They were very quiet. We also went wine tasting and visited a cheese factory. The location was great. We would happily stay in this property again."
The price is AU$493
includes taxes & fees
28 May - 29 May
Santa Rosa Serenity: Cozy 1bd Perch Amidst Wine Country
Pool
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
9.8 out of 10, Exceptional, (46)
"This beautiful home was wonderful for our extended families. The large open living area with a huge table and open kitchen made being together, talking and catching up so enjoyable while we cooked, and celebrated two birthdays. The outdoor area is lovely with plenty of seating, outdoor grills and pool with hot tub. Exquisite!"
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
Exterior
Lazy Bear Lodge- Enchanting Upscale Cabin! Cozy/Private/HotTub/Decks/PupOk
9.6 out of 10, Exceptional, (36)
"This was our first time visiting Guerneville. The town is nice and quaint— cute shops and local restaurants to eat, and only a short drive to the coast with lots of hikes and beaches that were dog friendly. The house itself is gorgeously tucked against the redwood forest. It is a nice modern home with all the amenities you would want. We absolutely loved the deck and hot tub. Property management was quick to respond as our reservation was booked only the day before."
Lazy Bear Lodge- Enchanting Upscale Cabin! Cozy/Private/HotTub/Decks/PupOk
Property grounds
Luxurious Wine Country Estate
10.0 out of 10, Exceptional, (1)
"We recently stayed at this place and it was wonderful for a large group. Geyserville is a fun little town and Hope Merrill mansion was perfect. Audra the owner is a pleasure too! We will be back"
Luxurious Wine Country Estate
Fridge, microwave, oven, stovetop
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
Outdoor pool
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
10.0 out of 10, Exceptional, (14)
"For a girls weekend, we stayed at this gorgeous home in Healdsburg. We were greeted by Adam who'd kindly set up a private wine tasting next door, where we enjoyed a wonderful history of the property, while tasting delicious wines... (and purchasing quite a few:) The home itself was bright, an open layout and comfortably housed five ladies. Every detail was impressive, from the gas fireplace, yoga mats, and even earplugs, just in case. Location was close to town, easy freeway access (without the...
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
TV, DVD player
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach
9.4 out of 10, Exceptional, (8)
"We had a wonderful time at Villa Eileen. The house was clean, in a great location and had a stellar view of the river. The kitchen was very well stocked and we were able to easily make dinner for all seven of us. We didn’t get to enjoy the yard and beach access because of rain and flooding but it looked awesome. The home seemed bigger in the photos. The walls were also a bit thin so we could hear grandpa snoring in the next room. But all in all it was a great home and we’d stay here again."
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach
Property grounds
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
Property grounds
NEW! Local Winemaker's 6 BDRM & VIP Wine Tasting!
9.6 out of 10, Exceptional, (13)
"This home is very clean and comfortable. Real plus is the 6 bedrooms. Good location, very close to shopping, restaurants and Starbucks. Nice neighborhood, felt very safe. I'm only giving it a 4 star rating because communication with the host was disappointing. It took 1 VRBO message and 1 phone call to receive our check-in instructions - 24 hours prior to check-in. Took 3 hours to fix a smoke detector beeping every 5 minutes. She also didn't respond to a message requesting reservations at their...
The price is AU$801
includes taxes & fees
27 May - 28 May
NEW! Local Winemaker's 6 BDRM & VIP Wine Tasting!
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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

Property grounds
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (148)
"Wonderful property, perfect for a get away. All amenities are top notch! Thank you!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Golf
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (156)
"We had a great experience at Fitch Mountain Lookout. The home has a great view, is a short walk downhill to the river, and only a short drive to town. We most enjoyed watching the birds come to the feeders in the morning while we started our day in the hot tub!"
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Exterior
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"
Chalk Hill Cottage Close to Wineries
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.

Healdsburg Holiday Homes information

Number of reviews
979
Accommodation
195 Holiday Homes
Lowest Price
Highest Price

Recent Reviews in Healdsburg
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