
Cottage vacation rentals in Healdsburg
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Top-rated cottage rentals in Healdsburg
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Vacation rentals for every style
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Popular amenities for Healdsburg cottage rentals
Cottage rentals with a pool

Luxury Sonoma Cottage: Sanctuary with Pool!
Sarah is a great host, very respectful, communicative and generous. Would stay in this place again if we get to visit Sonoma.

Deluxe Cottage - Single Queen/Double Twin
Loved it! Easily clean, I’d book here again.

Romantic Sonoma Creek Cottage With Pool & Spa
This is it if you are looking for privacy, comfort, and everything all in one place. We literally had to make ourselves leave the property… the babbling brook provided such serenity, and the pool, hot tub, and outdoor shower were amazing!!!

Farm Cottage With Private Pool
I can’t say enough positive things about this beautiful home. It was a little bit of magic in Sonoma county, very close to the town center but private and in the valley surrounded by fields. The home was gorgeous with beautiful linens and towels and a perfectly stocked kitchen.

Cozy Creekside Cottage near Lake Berryessa & Napa
Very relaxing and staff was extremely friendly and helpful

The Cabernet Cabin
This is our second time back to the Cabernet Cottage at Isis Oasis. We so much appreciate the funky nature of the place with its rich history. All of the wild animals are amazing and so fun to stroll the grounds with our boy. We are so impressed with the good work they do, funding their transitional housing with the proceeds from their rentals. Di Tracy and Justin were super generous and just very kind people.

Country 1BR Mountainview | Private Pool | Hot Tub
Wonderful cottage! Cozy, clean and peaceful. It was a perfect stay with all the amenities for a relaxing getaway in wine country. Even more beautiful than the pictures.

Idyllic Sonoma Vineyard Farmhouse With Pool
The most incredible home and location!! So far exceeded our expectations!! The setting was gorgeous and serene and perfectly located - short drive to amazing restaurants and vineyards!! We’re already searching for our next opportunity to visit this amazing property!! Couldn’t recommend it more!!!
Cottage rentals with a hot tub

Hillside Retreat in the Redwoods w/ Hot Tub
David's home in the Guerneville redwoods was a magical place for a solo retreat. The beauty and attention to detail was wonderful - from the art to the amenities to the guidebook! David was very responsive and kind in his communications. Would stay again.

WiLD Vines Winery and Farm Cottage
Magnificent gardens and setting, immaculate interior and super attention to character and detail, bery welcoming and homey, terrific outdoor spaces for sitting and dining

Story-Book Cottage in the Heart of Wine Country
This is a charming place, beautifully kept with lovely furnishings. We really enjoyed the well appointed kitchen as we cooked every day. The yard and gardens are beautifully kept, peaceful and serene. Oranges growing right outside the house! We were in town for a wedding, and Santa Rosa is right in the middle of so many enjoyable things to do. We hiked on the CCT out past Bodega Bay, enjoyed restaurants in Healdsburg, visited the redwoods and shopped at the Barlow in Sebastopol. Thank you Cheryl for sharing your lovely home. We had a fabulous time!

Riverfront Remodel | Hot Tub | Stunning Views
This is a perfect location for a tranquil getaway on the Russian River. Quiet neighborhood, easy walk to the store and to the welcoming, relaxing community coffeeshop- so good! The house was perfect: very clean and well cared for, kitchen well stocked for cooking, plenty of linens, so comfortable- we loved it! The location could not be better and the kindness of having river gear to use, plus the convenience of the outdoor shower- superb.

Red Door Retreat
This was our second time staying at Red Door Retreat and we had another great visit. As before everything was exactly as pictured and described. Checkin was very smooth and communication with Brett was great. We particularly enjoyed the several nice outdoor spaces and the hot tub. Quiet setting but short drive to local attractions and Guerneville town center. Highly recommended!

Napa Wine Country Retreat - Villa
My family and I had an enjoyable weekend stay at Peter’s cottage. The location was beautiful and home was cozy. The kitchen had everything we needed and I appreciated a clean porta-crib that was provided.

Riverwood Cottage - Hot Tub, Direct River Access!
Beautiful property! It was breathtaking to sit on the lawn and just hang out. So welcoming and had everything you could need

Alpine Ranch Farmhouse ~ Wine Country
Everything was great the location was amazing, the place was clean and the host was very responsive. Thanks for the great stay.
Pet-friendly cottage rentals

Cute Wine Country Cottage
Beautiful, quiet, and cozy. Super responsive hosts. Would love to come back someday.

Historic Cuneo Cottage Downtown Sonoma
We had a wonderful girls’ weekend in Sonoma staying at this lovely cottage! The location is super walkable to both the square and to nice hiking trails. Everything was spotless and the beds were comfortable. Highly recommend!

Seaside Sanctuary • Perched Over the Bay • Dogs OK
Fabulous stay with my mom and brothers! We were celebrating my mom's 70th but in a peaceful, quiet, getaway as we all needed a break from work badly...this cute waterfront cozy home did the trick! We had such a lovely time together and hope to come back one day. We visited for 4 nights in May. A little chilly at night so pack layers. The days were warm and sunny! We even had one day of light rain. Well worth it. Hidden gem in Marshall/Tomales Bay :)

Garden house with gas fireplace
A wonderful, fun place to stay! Super comfy & looking forward to visiting again, soon!!

Guerneville Cabin Among the Redwoods + Wineries
We loved Sarah and Keith’s house! Great location, close to everything, quiet, great neighborhood. We would definitely stay here again.

Dillon Beach Surf Cottage
We had a wonderfully relaxing stay at Dennis and Dan’s amazing cottage! The view was amazing and the beach less than a 5 mins walk away. We walked down to the beach for long walks with our dogs twice daily, they had a ball! It’s wonderful to be able to let your dogs run off leash on a beach, there are so few places in CA that you can. We had planned on venturing out but found ourselves glued to the deck people watching, listening to the waves and chilling out. The cottage was immaculate! We’ve never stayed in a place that is so well stocked with everything you could possibly need. The hosts have literally thought of everything! We couldn’t leave without first booking for next year.

Cozy Creekside Retreat in Sonoma Wine Country
Amazing stay! Very peaceful, beautifully surrounded by nature, nice and quiet. Very spacious and super clean, great for travelers with dogs. Only advice: bring a flashlight as it gets very dark at night and it will help if you have to take the pups out around the vicinity and/or if you arrive late at night.

Gravenstein Cottage
I had the very BEST stay at Mark's place! Everything about the stay was magical - the cottage was quaint and lovely, surrounded by redwoods. Mark's hospitality was of the very best I have seen...he was so kind, helpful and caring and lovely to talk with during the stay. He cares so much and wants to make sure his guests have the best experience. And wow the baked goods are incredible! This was the best mini retreat I could have imagined..I will definitely be back!
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- Lake Berryessa
- Jenner Beach
- Bolinas Beach
- Clam Beach
- Drakes Beach
- Limantour Beach
- Six Flags Discovery Kingdom
- Point Reyes National Seashore
- Schoolhouse Beach
- Chandon
- Dominus Estate
- Santa Maria Beach
- Doran Beach
- Bowling Ball Beach
- Cooks Beach
- Safari West
- Caymus Vineyards
- Mayacama Golf Club
- Sonoma Coast State Park
- Pebble Beach
- Portuguese Beach
- North Salmon Creek Beach
- Silver Oak Cellars
- Sea Ranch Golf Links