Healdsburg Vacation Rentals

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Nov 8 - Nov 9
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Nov 9 - Nov 10
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Nov 14 - Nov 16
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Nov 21 - Nov 23

Vacation Rentals in Healdsburg

Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Guerneville
10.0 out of 10, Exceptional, (1)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Interior
Walk to Russian River - Casa Del Rio - Unit A

Walk to Russian River - Casa Del Rio - Unit A

Forestville
9.2 out of 10, Wonderful, (38)
"Lovely home for a holiday get away"
United States
Cleo C.
The price is ￥16,876
￥59,097 total
includes taxes & fees
Nov 17 - Nov 18
Walk to Russian River - Casa Del Rio - Unit A
Property grounds
Healdsburg Plaza Gem | A Wine Country Escape

Healdsburg Plaza Gem | A Wine Country Escape

Healdsburg
9.8 out of 10, Exceptional, (44)
"Clean, good location,"
United States
Carrie B.
The price is ￥43,309
￥118,618 total
includes taxes & fees
Nov 11 - Nov 12
Healdsburg Plaza Gem | A Wine Country Escape
Exterior
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Windsor
9.2 out of 10, Wonderful, (43)
"Great location near brewing restaurant, great amenities for kids. Place was bigger than expected and fit adults and kids comfortably. Easy parking and access.Only complaint was that the timeshare staff spent 15 mins with me after checkin trying to get me to signup for a time share meeting, when I was alone trying to watch my two young children who did not want to sit still. I didn’t realize it was a timeshare facility and that might be my fault. "
United States
Nicole D.
The price is ￥34,520
￥86,051 total
includes taxes & fees
Nov 24 - Nov 25
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor spa tub
Redwood River House | A Wine Country Escape

Redwood River House | A Wine Country Escape

Healdsburg
9.4 out of 10, Exceptional, (65)
"Great location, close to wineries and downtown Healdsburg. Would highly recommend this place to others. We thoroughly enjoyed our stay! We went with another couple and both bedrooms were great!"
United States
Alyssa E.
The price is ￥34,796
￥111,547 total
includes taxes & fees
Nov 23 - Nov 24
Redwood River House | A Wine Country Escape
Exterior
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

Guerneville
9.4 out of 10, Exceptional, (3)
"Nice, quiet stay."
United States
Adam M.
The price is ￥33,955
￥49,684 total
includes taxes & fees
Nov 20 - Nov 21
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Terrace/patio
Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard

Guerneville
10.0 out of 10, Exceptional, (1)
"The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative."
United States
Beth G.
The price is ￥23,891
￥62,058 total
includes taxes & fees
Nov 20 - Nov 21
Redwoods getaway w/ decks & fenced yard
Terrace/patio
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Guerneville
10.0 out of 10, Exceptional, (43)
"A great place to stay if you want access to redwoods, ocean and wineries! Lexi was a super host and the stay was clean, organized and charming. We enjoyed the deck and hot tub in the evenings. Perfect for a long weekend!"
United States
Angie B.
The price is ￥35,943
￥70,571 total
includes taxes & fees
Nov 20 - Nov 21
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Wineries & Wine: A Comforting Getaway in Wine Country

Northwest Santa Rosa
9.4 out of 10, Exceptional, (22)
"Residence matches online description. Hosts are communicative. We found the location to be easy to get to/from when exploring wine country. "
United States
Meg H.
The price is ￥31,508
￥69,785 total
includes taxes & fees
Nov 19 - Nov 20
Wineries & Wine: A Comforting Getaway in Wine Country
TV, fireplace
Russian River Brew-cation Home

Russian River Brew-cation Home

Northwest Santa Rosa
10.0 out of 10, Exceptional, (54)
"There were 3 couples with us and the property was perfect for our group. Each bedroom had an attached bathroom, so we each had private space as well as common space to hang out. Great location close to everything."
United States
Andrea S.
The price is ￥32,578
￥77,833 total
includes taxes & fees
Nov 19 - Nov 20
Russian River Brew-cation Home
Property grounds
Rivers Breeze | A Wine Country Escape

Rivers Breeze | A Wine Country Escape

Healdsburg
10.0 out of 10, Exceptional, (17)
"Great place to stay!"
United States
Kim M.
The price is ￥39,951
￥118,395 total
includes taxes & fees
Nov 24 - Nov 25
Rivers Breeze | A Wine Country Escape
Fridge, microwave, oven, stovetop
Creekside Under the Redwoods

Creekside Under the Redwoods

Guerneville
10.0 out of 10, Exceptional, (13)
"Options"
United States
Christine
The price is ￥25,769
￥52,202 total
includes taxes & fees
Nov 20 - Nov 21
Creekside Under the Redwoods
Outdoor dining
Riverside love shack

Riverside love shack

2.0 star property
Forestville
The price is ￥25,940
￥66,525 total
includes taxes & fees
Nov 20 - Nov 21
Riverside love shack
Outdoor dining
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Forestville
10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
The price is ￥30,684
￥75,882 total
includes taxes & fees
Nov 17 - Nov 18
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Fridge, microwave, oven, stovetop
Sonoma Getaway: Winemaker’s Home with Modern Amenities

Sonoma Getaway: Winemaker’s Home with Modern Amenities

Northwest Santa Rosa
10.0 out of 10, Exceptional, (76)
"The house was very clean and cozy in a cute neighborhood. Very nice backyard space and interior, would definitely recommend and stay again."
United States
Gary R.
The price is ￥34,980
￥80,236 total
includes taxes & fees
Nov 16 - Nov 17
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Exterior
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

2.5 star property
Geyserville
9.2 out of 10, Wonderful, (13)
"Great property, spacious & unique space for large groups! The house, while a bit dated, was comfortable for all our guests. The pool table was fun to have and although the pool is on the smaller side, it still worked out fine with our large group to mingle in & around. As another guest commented, the kitchen is a bit small for the size of the house but still worked out fine for us. The house features impressive, high ceilings throughout that add to its spacious, lodge like charm. We did notice...
United States
Joe V.
The price is ￥68,349
￥141,816 total
includes taxes & fees
Nov 10 - Nov 11
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley

Northwest Santa Rosa
9.8 out of 10, Exceptional, (70)
"The property was very nice and well equipped. We would definitely stay there again!"
United States
Terry E.
The price is ￥36,821
￥81,735 total
includes taxes & fees
Nov 24 - Nov 25
Winemaker's Delight: 3BD/3BA Russian River Valley
Fridge, microwave, oven, stovetop
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Healdsburg
10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
United States
Theresa C.
The price is ￥32,900
￥67,542 total
includes taxes & fees
Nov 19 - Nov 20
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10

Windsor
10.0 out of 10, Exceptional, (2)
"Beautiful home and property. Great location, close to so many vineyards and other places we wanted to visit. Cynthia was so great to work with! Would definitely stay here again. "
United States
Denise F.
The price is ￥79,472
￥168,173 total
includes taxes & fees
Nov 9 - Nov 10
Private Vineyard Estate | Sleeps 10
Terrace/patio
Dragonfly Healdsburg | A Wine Country Escape

Dragonfly Healdsburg | A Wine Country Escape

Healdsburg
10.0 out of 10, Exceptional, (6)
"I booked this house knowing it was more than I needed for this trip, but was comparing it to a suite at one of the nice hotels in the vicinity. This home feels like you’re staying at a family or friend’s home. I wish I would have had more time there. The kitchen was well-appointed, and worked well (I cooked in both nights). The furnishings are very nice and the instructions are easy to follow for the pool, fire pit, etc. I’ll be back with more friends or family next time! "
United States
Kevin H.
Dragonfly Healdsburg | A Wine Country Escape
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

Appellation Healdsburg

Appellation Healdsburg

10/10 Excellent
"Great new spot. Great staff. "
Noah 1-night trip
Posted 3 days ago
Appellation Healdsburg

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:

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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 vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, or you can choose a secluded option if you want 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's the top vacation rental that Healdsburg has to offer?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This vacation home rental outside of Healdsburg is located by the ocean and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Healdsburg?

Expedia has 136 vacation 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 vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.