Cottage vacation rentals in Healdsburg

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Popular amenities for Healdsburg cottage rentals

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, 280 reviews

Hillside Retreat in the Redwoods w/ Hot Tub

TaylorRating, 5 stars1 week ago
House matches pictures exactly - well worth it for a nice getaway. The road is typical for the area - it is narrow towards the last bit but it is fine. People were driving large SUVs up the hill with no issue. It was nice that this Airbnb is dog friendly and doesn’t have crazy outlandish rules like others in the area. The only feedback I have is I don’t like when Airbnbs have extensive checkout rules. I always find it odd to pay a cleaning fee but also be required to do a lot of pre cleaning in advance like loading the dishwasher and stripping the beds. Other than that, no complaints. Would definitely come back again as it’s convenient for the area and close enough but still feels quiet and secluded.
Superhost
An outdoor fire pit surrounded by four wooden chairs offers a welcoming gathering space. The stone patio extends outward, framed by lush greenery and the vibrant hues of sunset. A vineyard is visible in the background, enhancing the natural setting.
Cottage in Sebastopol
4.92 out of 5 average rating, 316 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

TaylorRating, 5 stars2 days ago
My husband and I spent 3 nights at the lodge for our one year wedding anniversary. It is located on the same property as their vineyard which makes for a beautiful, serene view and setup. During our stay, we did a very personal wine tasting with David in the main house. It truly is a cool experience and unlike any other wine tasting I have done before, not to mention the wine was very good! The lodge itself is cozy and relaxing with a private back patio looking into the trees and nature. I wasn’t so sure about the outdoor shower at first but it was actually really nice! Water warmed up really fast and the view is amazing. The bed is located upstairs which was very comfortable and cozy with plenty of pillows and blankets. If you have trouble with mobility, the stairs leading to the bedroom are not easy to navigate and there are more stairs from the parking lot to the lodge with some uneven ground at times. If you are fine with stairs and some walking, it is well worth it!
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 Santa Rosa
4.99 out of 5 average rating, 103 reviews

Story-Book Cottage in the Heart of Wine Country

HarryRating, 5 stars1 month 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 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, 174 reviews

WiLD Vines Winery and Farm Cottage

AmandaRating, 5 stars2 months ago
This was a perfect spot for a personal retreat. I loved everything from the decor to the comfy bed to the private hot tub and well tended garden. I would love to come back again.
Guest favorite
The exterior of the cottage features a charming gray facade with white trim and a welcoming entrance. Colorful roses bloom along the stone path leading to the door, while greenery surrounds a sunlit patio area, creating a peaceful outdoor space.
Cottage in Sonoma
4.94 out of 5 average rating, 102 reviews

Andrea's Hidden Cottage

SamanthaRating, 5 stars3 weeks ago
Super cute little spot. Walking distance to Sonoma Plaza and it had a private hot tub. Good distance from some vineyards and wineries as well!
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, 194 reviews

Napa Wine Country Retreat - Villa

MeredithRating, 5 stars1 month ago
This home is absolutely beautiful! The outside is gorgeous and relaxing. The outdoor patio and hot tub are amazing! The location is also fabulous. We went to the Bothe-Napa state park and the Castello di Amorosa both of which were only 15min away as is downtown Calistoga which is really cute. We really enjoyed our stay!! The only slightly problematic feature is the toilet, it doesn’t really work.
Top guest favorite
Cottage in Monte Rio
4.98 out of 5 average rating, 183 reviews

Riverfront Cottage w/ lush gardens & hot tub!

KellyRating, 5 stars3 weeks ago
If you're planning an escape in the Duncan Mills area, this is the place you want to be. It is conveniently located as a great jumping off point for all the local area has to offer or provides the perfect place for relaxation and reflection if that's what you need. Karen is a super host and very responsive should anything arise. The amenities at the River cottage cannot be understated. From the stocked kitchen to outdoor decks and gardens complete with hot tub and outdoor soaking tub there is something for everyone. My wife and I thoroughly enjoyed our stay and look forward to another visit in the future. Consider a stay at Mama K's River Cottage, you'll be glad you did.
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
4.87 out of 5 average rating, 204 reviews

Riverwood Cottage - Hot Tub, Direct River Access!

BreonnaRating, 5 stars4 days ago
Our family of three had a wonderful time at Riverwood! We appreciated the thoughtful touches -tea kettle, garlic press, as well as books and guides to local history, flora and fauna. The home was clean and comfortable, and the grounds were enchanting! Buttercups bloomed along the path to the river, and the redwood trees towered overhead. The back porch offered a gorgeous view and vantage point to enjoy the birds and wildlife! Don't forget your binoculars! While it was foggy during our springtime stay, the hot tub, claw foot bathtub and fireplace kept us cozy. Town, river beaches, Armstrong Redwoods state park and Jenner by the Sea are all easily accessible from the property's location. Riverwood was a very peaceful and beautiful place to be! Sangeeta was a communicative and attentive host. We had a seamless stay, and no problem finding the property. Communication and directions were all very clear and detailed. Thank you for a lovely stay!

Pet-friendly cottage rentals

Guest favorite
The entrance of the cottage is framed by a wooden gate leading to a gravel pathway. The facade showcases a cozy craftsman style with a gray exterior, white trim, and large windows. A welcoming wreath is placed on the front door, and the surrounding greenery adds to the charm.
Cottage in Santa Rosa
4.87 out of 5 average rating, 182 reviews

Cute Wine Country Cottage

WinstonRating, 5 stars4 days ago
Wonderful place for our group to stay! The house was exactly as described, and everybody had plenty of space to themselves. The house was very clean and is located in a great spot in town.
Guest favorite
Cottage in Marshall
4.89 out of 5 average rating, 296 reviews

Seaside Sanctuary • Perched Over the Bay • Dogs OK

AmyRating, 5 stars3 weeks ago
The first thing you notice is the waves from all directions. You immediately feel at peace. All the amenities were easy to locate and good quality, including great pots and pans, knives dishes and gadgets for cooking. There were extra linens and towels, it was comfy upstairs and down. It was well laid out and you look out at Point Reyes and Tomales Bay while lying in bed upstairs. The stairs were quite steep but there was a nice bedroom downstairs as well. I enjoyed the heated ceramic floor in the downstairs bathroom and there was good water pressure. We loved the wide wraparound deck and dock, as well as outdoor tables and a garden. The beds and sofas were all very good quality and comfortable and it was nice to have the fireplace. The dog had room to sniff and roam safely at will as the decks and garden were well enclosed. Hog Island is one minute away, Tony’s five minutes away for the chowder, and truly awesome pizza at Route One on the way to the dog beach at Dillon. Thanks!
Guest favorite
A cozy living area is seen with a comfortable leather love seat, complemented by decorative pillows. A rustic table and chairs provide a dining space, while a large window invites natural light. A wall-mounted television is positioned for viewing, enhancing the room's functionality.
Cottage in Middletown
4.97 out of 5 average rating, 118 reviews

Garden house with gas fireplace

ArunRating, 5 stars3 weeks ago
pleasant and cozy stay. definitely recommend to unwind and relax
Guest favorite
Two inviting lounge chairs in turquoise are positioned beside a serene creek, surrounded by lush greenery. The tranquil water reflects the sunlight and the trees overhead, creating a peaceful outdoor setting ideal for relaxation.
Cottage in Glen Ellen
4.91 out of 5 average rating, 282 reviews

Cozy Creekside Wine Country Retreat #2

LindseyRating, 5 stars1 week ago
Laying by the river on the deck with my two senior doggos was pure bliss!
Guest favorite
A rustic wooden house resides among lush greenery, featuring large windows that invite natural light. A simple outdoor seating area, with benches and tables, is positioned on a gravel path, surrounded by vibrant foliage and garden plants, contributing to a serene atmosphere.
Cottage in Occidental
4.95 out of 5 average rating, 701 reviews

The Perch

MilesRating, 5 stars2 weeks ago
This little cabin in the woods is exactly as presented. Unbeatable setting for nature lovers and those looking for a retreat from urban/suburban areas, yet still only 30 min from wine country and nearby towns. Would definitely stay again, and recommend to any who love how it presents in photos.
Superhost
Cottage in Hidden Valley Lake
4.86 out of 5 average rating, 51 reviews

Windmill Cottage: A Peaceful & Private Retreat

ErinRating, 5 stars2 weeks ago
Joshua’s place was perfect. The home was beautiful and the surrounding area was great. The home is set back on a quiet street, which made enjoying the home so relaxing. I brought my two dogs who enjoyed sunbathing on the wrap around patio/deck and running around the yard. Would definitely recommend and hope to visit again!!
Guest favorite
A quaint backyard setting features a picnic table with a red umbrella, surrounded by greenery. An outdoor chair sits nearby, and a charcoal grill is visible. A small dog is seen near the patio, while a person enjoys a drink with a plate of snacks.
Cottage in Dillon Beach
4.97 out of 5 average rating, 144 reviews

Sundog - EV - Walk to Beach & Food - Yard for Dog

MollieRating, 5 stars1 month ago
Sundog cottage is lovely! We were so happy to find that it was even more beautiful in person than the pictures. Super clean, great kitchen, deck and backyard were perfect for our dogs and just relaxing and listening to the ocean. The linens are amazing and the beds comfy! Valerie went above and beyond as a host, even left us local eggs, butter and crackers. She was friendly and easy to communicate with. Sundog is a gem and we can’t wait to come back!
Superhost
A comfortable seating area features a large, L-shaped couch adorned with decorative pillows. A rustic coffee table sits in front, while a television is positioned on a wooden media console. Natural light floods the space through multiple windows, enhancing the cozy atmosphere.
Cottage in Dillon Beach
4.81 out of 5 average rating, 36 reviews

Resort 61

MichelleRating, 5 stars3 months ago
The house was very comfortable and perfect for a family get away! I loved the proximity to the beach. She allows a dog which is great.

Private cottage rentals

Guest favorite
A kitchen nook features light-colored cabinetry and open shelving. Glassware is displayed above a wooden countertop, while a sink is visible on the left. Natural light filters through a window, illuminating the organized space with a view of the outdoors.
Cottage in Guerneville
4.89 out of 5 average rating, 9 reviews

Schooners Hideaway

AlyssaRating, 5 stars8 months ago
Just returned from a wonderful weekend at the cottage! This was the most ideal location, in walking distance to everything and a grocery store a stone throw away! The house was clean and comfortable, we would definitely recommend and are also excited to return. Thanks Marta for being such a responsive host!
Top guest favorite
A serene outdoor seating area is situated near a gently flowing creek. Four dark wooden chairs surround a circular concrete fire pit, set on a sandy base. Vibrant yellow leaves hang from nearby trees, enhancing the natural ambiance of this retreat.
Cottage in Kenwood
5 out of 5 average rating, 21 reviews

Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi

KaleyRating, 5 stars1 week ago
I cannot say enough good things about this place. The ambience, decor, and peaceful outdoor setting was absolutely perfect. One of the best places I’ve ever stayed at! Truly even better than some 4-5 star hotels in Europe I’ve visited. This home is beautiful. It’s clean. It’s just perfect. Thank you so much for such a memorable and beautiful stay!
Guest favorite
A private entrance is framed by stone pillars and wooden gates, leading to a well-maintained asphalt driveway. Surrounding greenery and low-maintenance landscaping enhance the secluded feel of the property.
Cottage in Healdsburg
4.78 out of 5 average rating, 54 reviews

Charming Cottage in Healdsburg Wine Country

KristinRating, 5 stars1 month ago
Enjoyed our stay here. Felt safe with the gated entrance. Location's great about a 12 minute drive to Healdsburg. Great space layout and enjoyed the fireplace in the living room.
Top guest favorite
The open living area features light wood flooring and a contemporary layout. A bright red sofa and blue ottoman are placed in front of a mounted flat-screen TV. An electric fireplace adds warmth, while natural light fills the space through the windows.
Cottage in Cotati
5 out of 5 average rating, 24 reviews

Redtail Hawk Cottage | Private & Sparkling New

DeniseRating, 5 stars3 weeks ago
Great place!! Easy to find and felt nice and peaceful and secluded even though there are houses around. It had everything we needed to relax for a couple days!! Super nice fenced in back yard. Beautiful home!! Would definitely pick this place to stay if through the area again!!
Guest favorite
A charming cottage exterior is surrounded by towering Redwoods, featuring a spacious patio area with Adirondack chairs and a stone pathway. Soft lights hang overhead, creating a cozy ambiance in the tranquil garden, complemented by natural greenery throughout the setting.
Cottage in Monte Rio
4.98 out of 5 average rating, 51 reviews

Cottage C - Comfy and Cozy 1 bed 1 bath cottage

LaelRating, 5 stars2 weeks ago
About as good as an Airbnb gets, in my opinion. Just a lovely stay from start to finish. The cottage is cozy and situated in a very peaceful, beautiful setting, surrounded by towering redwoods, a little creek runs right alongside the property, and the hillside is lush with ferns. The cottage has amazing views from every window, but thick, easy to close curtains for privacy and sleeping late. The king size bed was perfectly firm and clean with nice cotton sheets and comforter. The kitchen was perfectly stocked with everything you could need, and it was easy to pair my phone to the Sonos speaker system for music. The hot tub is enormous, and just perfectly situated, so it felt very private and safe. All in all, everything about the place gets and A+! We didn’t interact with Tom beyond a few words at check-in, but he was warm and welcoming. We had zero problems, but when I messaged him to let him know we were checking out, he responded almost immediately. I hope we can stay here again!
Guest favorite
A wooden deck features a railing overlooking the serene river. Two blue chairs are positioned on the deck, with trees lining the riverbank. The clear blue sky and gentle clouds complement the tranquil river scene, enhancing the natural surroundings.
Cottage in Healdsburg
4.88 out of 5 average rating, 83 reviews

Riverfront Wine Country Cottage With Views and Spa

ValentinaRating, 5 stars3 months ago
The house feels like a cabin in the woods--it is quiet with a view of the river and thousands of stars above. We loved the wood-burning stove, the hot tub, and the cozy wood living room. It was close to downtown Healdsburg but felt like a mountain getaway.
Superhost
A panoramic view of the coastline showcases rugged cliffs meeting the ocean. Waves gently crash against large rocks, while a clear sky and distant hills create a serene backdrop. The natural beauty of the area is highlighted by the varying blue tones of the water.
Cottage in Bodega Bay
4.5 out of 5 average rating, 4 reviews

Bodega Bay Oyster Cottage

HeatherRating, 5 stars8 months ago
This cottage is an absolute gem! It was so cozy and comfortable. It was impeccably clean. The linens and furnishings are top-notch. The bay view is fantastic. The host was responsive and friendly. We’ll return for sure!
Superhost
Cottage in Calistoga
4.92 out of 5 average rating, 26 reviews

Luxury Cottage in Downtown Calistoga - Accessible

AmandaRating, 5 stars3 weeks ago
Quaint cottage in Calistoga with coffee and restaurants within walking distance. Easy checkin and communication with the host. The room was clean and had a fire place and spa sized bath tub. We would definitely consider booking here again on our next trip to Calistoga.

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