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Vacation rentals in Chalk Hill AVA

Vacation rentals in Chalk Hill AVA

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chalk Hill AVA

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Downtown Cottage - Walk to Plaza!
    Entire guest house · 4 guests · 2 beds · 1 bathroom
    Downtown Cottage - Walk to Plaza!

    This adorable updated cottage located a few blocks from downtown is the perfect interim home, writer's retreat, or extended vacation spot for anyone who wants to enjoy everything Healdsburg has to offer. A fenced backyard welcomes your pet!

    What guests are saying:

    “The cottage is cozy and charming! It's located in a beautiful and very safe neighborhood. The back patio is a awesome private space to enjoy coffee in the morning or a glass of wine in the evening. There's a small fountain which goes perfect with the amazing song birds that seem to be everywhere! The cottage is just a hop, skip and a jump away from one of the most beautiful cities in America in my opinion. Sarah is a very sweet & thoughtful lady and she totally respected our privacy. She even gave us I lovely bottle of wine! I would describe our trip as magical, romantic and charming. The people in the city are incredibly friendly and it's truly a breath of fresh air in today's climate. It's well worth the price and I would highly recommend this host and home in particular to anyone that wants to visit Healdsburg!”

  • Healdsburg Garden House
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bathroom
    Healdsburg Garden House

    Super clean and sanitized Private, spacious & comfortable Homemade Grenache wine, fresh eggs and flowers Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in Bedrooms and Living Room (HBO, Showtime, Netflix, YouTube, +much more) WiFi High Speed Internet Large Sunny Covered Redwood Redwood Deck with Gas Grill Level Walk (1 mile) to Town Square and Russian River TOT # 798N

    What guests are saying:

    “Our timing just happened to be during the COVID-19 ‘shelter-in-place’ and this place was the perfect place to be stuck in on vacation! 😊 - communication was excellent of what was going on and great detail was taken to have the place cleaned and sanitized before we arrived . There were fresh eggs and wine for us and access to the garden and outdoor grill. There was a great market ‘Big John’s’ that is a short drive away. This wasn’t the vacation we originally planned - but having this place to stay helped us make the best of it.”

  • Luxurious, Private, Healdsburg Guest House
    Entire cottage · 2 guests · 1 bed · 1 bathroom
    Luxurious, Private, Healdsburg Guest House

    1083 Guest House is a Healdsburg find; comfortable luxury in a spacious private home with terrific amenities within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded home nestled in green space with views of the forest beyond is the perfect destination for your personal romantic getaway to enjoy all that the Wine Country has to offer. We also provide wine tour and weekend getaway packages. Regular price is $465-$550.

    What guests are saying:

    “Tami and Jim have something really special with their guest house. Beautiful vaulted ceilings, smart and warm design, brand new furniture and fixtures, great lighting, heating and AC (I was comfortable every day whether it be 96 degree weather during a heat wave and through rain). Where else can you sit in a brand new, well designed breakfast nook and watch deer and jack rabbits, hawks, bluejays and squirrels play an in an open field, or gaze upon stars and satellites from a comfortable terrace to the sounds of crickets and a fountain, or watch the sunset from a secluded hot tub? Also, I am 6'6" and Tami is right to be proud of the house's beautiful shower with enough headroom for anyone. It's all about the details. The french door closets in the bedroom have their own tasteful lighting. Tami and Jim were very good about giving me my space to write and work, but also checking in on me, and making sure I had everything I needed. I have come away from my time in Healdsburg feeling rested, refreshed, inspired and ready to handle life back in the big city. Thank you Tami and Jim. I hope to see you again for another visit.”

Holiday rentals for every style

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Popular amenities for Chalk Hill AVA holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chalk Hill AVA

Healdsburg ~ Elegant space, large patio, breakfast
SUPERHOSTPrivate room
Healdsburg ~ Elegant space, large patio, breakfast
Price:€152 / night
The Loft Under The Oaks
Entire loft
The Loft Under The Oaks
Price:€109 / night
Healdsburg Contemporary Cottage With Lush Backyard Patio
SUPERHOSTEntire guest house
Healdsburg Contemporary Cottage With Lush Backyard Patio
Price:€310 / night
Updated cabin on Russian River - fab views/beach!
SUPERHOSTEntire cabin
Updated cabin on Russian River - fab views/beach!
Price:€391 / night
Lovely room with private bath
SUPERHOSTPrivate room
Lovely room with private bath
Price:€60 / night
C - Wineries/breweries seconds away
SUPERHOSTEntire house
C - Wineries/breweries seconds away
Price:€142 / night
Wine Country Room in Windsor, close to everything!
SUPERHOSTPrivate room
Wine Country Room in Windsor, close to everything!
Price:€63 / night
The Doll House
SUPERHOSTEntire house
The Doll House
Price:€185 / night
Tranquil location, hot tub, fire pit, game room!
SUPERHOSTEntire house
Tranquil location, hot tub, fire pit, game room!
Price:€400 / night
Eclectic Healdsburg House (Monthly Rentals Only)
Entire chalet
Eclectic Healdsburg House (Monthly Rentals Only)
Price:€89 / night
Trinite Estate
Entire villa
Trinite Estate
Price:€843 / night
Wine wonderful!  Healdsburg 5 min!
SUPERHOSTEntire house
Wine wonderful! Healdsburg 5 min!
Price:€508 / night
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