Cottage vacation rentals in Healdsburg

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Popular amenities for Healdsburg cottage rentals

Cottage rentals with a pool

Cottage in Sonoma
4.88 out of 5 average rating, 51 reviews

Luxury Sonoma Cottage: Sanctuary with Pool!

LushiRating, 5 stars5 months ago
Sarah is a great host, very respectful, communicative and generous. Would stay in this place again if we get to visit Sonoma.
Cottage in Cobb
4.83 out of 5 average rating, 18 reviews

Deluxe Cottage - Single Queen/Double Twin

JessicaRating, 5 stars11 months ago
Loved it! Easily clean, I’d book here again.
Guest favorite
A private solar heated pool is surrounded by lush greenery and a stone patio. Several lounge chairs are positioned nearby for relaxation, with a shaded umbrella providing comfort. The pool's clear water reflects the blue sky, offering a serene atmosphere.
Cottage in Glen Ellen
4.97 out of 5 average rating, 62 reviews

Romantic Sonoma Creek Cottage With Pool & Spa

EmilyRating, 5 stars4 days ago
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!!!
Guest favorite
A solar-heated pool is set within a spacious patio of brick pavers. Two white lounge chairs sit beside the pool, accompanied by large umbrellas providing shade. Lush greenery and a wooden fence are visible in the background, enhancing the serene atmosphere.
Cottage in Sonoma
4.92 out of 5 average rating, 112 reviews

Farm Cottage With Private Pool

JocelynRating, 5 stars2 weeks ago
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.
Three rustic cabins are shown, each featuring a covered porch and wooden railings. A grassy area is visible in the foreground, with trees providing shaded spots. The background reveals a hilly landscape under a clear blue sky.
Cottage in Winters

Cozy Creekside Cottage near Lake Berryessa & Napa

BrendaRating, 5 stars1 month ago
Very relaxing and staff was extremely friendly and helpful
Superhost
A private hot tub is framed by brick and tile edging, with a smooth metal rail for easy access. Bubbles gently rise in the water, creating a relaxing atmosphere. Nearby, a larger swimming pool is visible, adding a sense of leisure to the space.
Cottage in Geyserville
4.41 out of 5 average rating, 260 reviews

The Cabernet Cabin

DouglasRating, 5 stars7 months ago
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.
A spacious deck surrounds an unheated pool, featuring multiple lounge chairs and umbrellas. Scenic views of rolling hills and vineyards are visible in the background under a clear blue sky.
Cottage in Kenwood
4.83 out of 5 average rating, 6 reviews

Country 1BR Mountainview | Private Pool | Hot Tub

KarlaRating, 5 stars26 months ago
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.
Top guest favorite
A clean and inviting pool area is showcased, featuring a recessed hot tub and a spacious swimming pool. In the background, a pergola provides shade over a seating area, with sunflowers and vineyard visible in the landscape.
Cottage in Sonoma
4.99 out of 5 average rating, 137 reviews

Idyllic Sonoma Vineyard Farmhouse With Pool

MaryRating, 5 stars10 months ago
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

Guest favorite
A spacious outdoor deck is surrounded by towering redwoods, creating a serene setting. Comfortable seating arrangements include a sectional sofa with yellow cushions and a low coffee table. String lights illuminate the space, while potted plants add a touch of greenery.
Cottage in Guerneville
4.98 out of 5 average rating, 288 reviews

Hillside Retreat in the Redwoods w/ Hot Tub

MelanieRating, 5 stars6 days ago
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.
Top guest favorite
A quaint entrance is framed by a wooden overhang, featuring two yellow Adirondack chairs placed on a stone patio. Nearby, potted plants sit under a blooming tree, contributing to a serene outdoor setting.
Cottage in Santa Rosa
4.97 out of 5 average rating, 178 reviews

WiLD Vines Winery and Farm Cottage

MikeRating, 5 stars3 weeks ago
Magnificent gardens and setting, immaculate interior and super attention to character and detail, bery welcoming and homey, terrific outdoor spaces for sitting and dining
Top guest favorite
A charming cottage features a well-maintained front yard adorned with lush greenery and colorful flowers. The inviting exterior showcases a mix of brick and stucco, with multiple arching doorways and windows, set against a tranquil evening sky.
Cottage in Junior College
4.99 out of 5 average rating, 104 reviews

Story-Book Cottage in the Heart of Wine Country

HarryRating, 5 stars3 months ago
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!
Top guest favorite
A modern living space features large floor-to-ceiling sliding doors that open to a wrap-around deck. Skylights allow natural light to fill the room. Comfortable seating includes two patterned chairs and a leather chair, creating an inviting atmosphere for relaxation.
Cottage in Monte Rio
5 out of 5 average rating, 226 reviews

Riverfront Remodel | Hot Tub | Stunning Views

SaraRating, 5 stars2 weeks ago
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.
Guest favorite
The quaint cottage is framed by tall redwood trees, showcasing a spacious front porch with a railing. A deck with wooden steps leads to the entrance, while the exterior features a light-colored facade and garage doors below. Lush greenery adorns the surrounding area.
Cottage in Guerneville
4.91 out of 5 average rating, 352 reviews

Red Door Retreat

StephenRating, 5 stars2 weeks ago
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!
Top guest favorite
A serene landscape features rolling hills adorned with golden grasses, leading to a distant view of the cabin nestled among green trees. The blue sky is complemented by a few clouds, creating a peaceful rural setting.
Cottage in Santa Rosa
4.94 out of 5 average rating, 198 reviews

Napa Wine Country Retreat - Villa

BethRating, 5 stars3 days ago
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.
Guest favorite
A deck with a glass table and four woven chairs overlooks the river and surrounding greenery. A vase of flowers sits at the center of the table. The expansive lawn and white loungers are visible in the background, framed by lush trees.
Cottage in Monte Rio
4.88 out of 5 average rating, 209 reviews

Riverwood Cottage - Hot Tub, Direct River Access!

JanaRating, 5 stars3 days ago
Beautiful property! It was breathtaking to sit on the lawn and just hang out. So welcoming and had everything you could need
Top guest favorite
The living room features a spacious sectional sofa paired with vibrant accent chairs, arranged around a natural fiber rug. A brick fireplace is the focal point, while large glass doors provide access to the outdoor area. Natural light floods the space through skylights and windows.
Cottage in Santa Rosa
4.97 out of 5 average rating, 222 reviews

Alpine Ranch Farmhouse ~ Wine Country

ParastooRating, 5 stars2 weeks ago
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

Guest favorite
The exterior of a charming craftsman cottage showcases a well-maintained yard with a stone walkway and wooden fence. Lush greenery surrounds the house, while a clear blue sky complements the exterior's inviting design. A porch area is visible, enhancing the welcoming appearance.
Cottage in Santa Rosa
4.88 out of 5 average rating, 188 reviews

Cute Wine Country Cottage

CristinaRating, 5 stars2 weeks ago
Beautiful, quiet, and cozy. Super responsive hosts. Would love to come back someday.
Superhost
A historic stone cottage is framed by lush greenery and well-maintained lawns. The front porch, supported by carved posts, provides a welcoming entrance. Surrounding palm trees add to the serene ambiance, enhancing the cottage’s character against a clear blue sky.
Cottage in Sonoma
4.87 out of 5 average rating, 135 reviews

Historic Cuneo Cottage Downtown Sonoma

CarolineRating, 5 stars1 month ago
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!
Superhost
A charming green cottage sits at the water's edge, featuring a vibrant red door. White Adirondack chairs are positioned on the deck, providing a serene view of Tomales Bay at sunset, with soft hues illuminating the sky and water.
Cottage in Marshall
4.89 out of 5 average rating, 299 reviews

Seaside Sanctuary • Perched Over the Bay • Dogs OK

CarlaRating, 5 stars4 weeks ago
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 :)
Guest favorite
The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.
Cottage in Middletown
4.98 out of 5 average rating, 123 reviews

Garden house with gas fireplace

DanielleRating, 5 stars1 week ago
A wonderful, fun place to stay! Super comfy & looking forward to visiting again, soon!!
Superhost
The cottage is nestled among towering redwoods, featuring a large front porch and wooden steps leading to the entrance. A gravel path is surrounded by greenery, and a rustic outdoor area is visible on the side, enhancing the serene setting.
Cottage in Guerneville
4.87 out of 5 average rating, 108 reviews

Guerneville Cabin Among the Redwoods + Wineries

DavidRating, 5 stars2 weeks ago
We loved Sarah and Keith’s house! Great location, close to everything, quiet, great neighborhood. We would definitely stay here again.
Top guest favorite
A spacious deck features striped lounge chairs positioned for optimal views of the ocean. The surrounding area includes multiple cottages with metal roofs, set against a clear blue sky. The peaceful setting is enhanced by the distant coastline.
Cottage in Dillon Beach
4.98 out of 5 average rating, 357 reviews

Dillon Beach Surf Cottage

SharonRating, 5 stars2 weeks ago
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.
Guest favorite
A living area features a blue velvet sofa adorned with decorative pillows. A glass coffee table sits on a patterned area rug, and a cozy chair is positioned nearby. Natural light filters through the window, with a pet-themed photo displayed on the wall.
Cottage in Glen Ellen
4.91 out of 5 average rating, 291 reviews

Cozy Creekside Retreat in Sonoma Wine Country

LizetteRating, 5 stars2 weeks ago
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.
Guest favorite
The exterior of Gravenstein Cottage features a welcoming porch with wooden steps leading up to a yellow framed entrance. Flourishing greenery surrounds the cottage, enhancing the natural ambiance of the serene woodland setting.
Cottage in Cazadero
4.9 out of 5 average rating, 344 reviews

Gravenstein Cottage

GinaRating, 5 stars1 month ago
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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