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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Healdsburg

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

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

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!"
The price is NZ$836
includes taxes & fees
17 Aug - 18 Aug
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Windmill Cottage - Peaceful & Quiet on 5 acres
Dining

Windmill Cottage - Peaceful & Quiet on 5 acres

10.0 out of 10, Exceptional, (12)
"Joshua was the best host! "
The price is NZ$728
includes taxes & fees
21 Aug - 22 Aug
Windmill Cottage - Peaceful & Quiet on 5 acres
Charming 2-bedroom cottage with AC and WiFi in Clearlake ON THE LAKEFRONT
Property grounds

Charming 2-bedroom cottage with AC and WiFi in Clearlake ON THE LAKEFRONT

The price is NZ$561
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom cottage with AC and WiFi in Clearlake ON THE LAKEFRONT
Garden house with gas fireplace
Outdoor dining

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
The price is NZ$376
includes taxes & fees
3 Sept - 4 Sept
Garden house with gas fireplace
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (49)
"Cute garden area, quiet, nice all inclusive spot"
The price is NZ$365
includes taxes & fees
27 Aug - 28 Aug
Backyard Garden Oasis
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (21)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is NZ$691
includes taxes & fees
1 Sept - 2 Sept
Escape to Wine County in your independant Cottage in Downtown Calistoga
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine Country in your independant Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
The price is NZ$690
includes taxes & fees
19 Aug - 20 Aug
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
The price is NZ$693
includes taxes & fees
16 Sept - 17 Sept
Escape to wine country in your independent cottage in downtown Calistoga
The Atlas Calistoga - Cottage #2
Iron/ironing board, travel cot, WiFi, bed sheets

The Atlas Calistoga - Cottage #2

10.0 out of 10, Exceptional, (18)
"We recently had a lovely stay. Very conveniently located just a short walk to downtown. Great layout, with a king bed, fireplace, cute small patio with chairs, huge bathroom and a little fridge & coffee station area. The host was super responsive and provided great recommendations for local wine tasting and dinner locations. Lovely small town with cute shops, breakfast & bakery options, wine bars and restaurants. We had a great stay and will definitely be back!"
The price is NZ$836
includes taxes & fees
16 Sept - 17 Sept
The Atlas Calistoga - Cottage #2
Charming King Cottage
Property grounds

Charming King Cottage

9.8 out of 10, Exceptional, (11)
"Cozy and great price!"
The price is NZ$445
includes taxes & fees
24 Aug - 25 Aug
Charming King Cottage
Comfort and Style in Our Queen Cottage
Dining

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (48)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
The price is NZ$405
includes taxes & fees
17 Aug - 18 Aug
Comfort and Style in Our Queen Cottage
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
Terrace/patio

Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included

4.5 star property
9.0 out of 10, Wonderful, (2)
"Such a cute place! The turn into the property is a bit hidden right before the bridge but once you find it the house is so secluded with plenty of space. The kitchen was fully stocked and had everything you could think of. Did a wine tasting with their tasting room and everyone was so welcoming and sweet. Thank you! "
The price is NZ$1,064
includes taxes & fees
18 Aug - 19 Aug
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
Modern Sonoma Farmhouse on Vineyard w Deck + Bocce Court
Outdoor dining

Modern Sonoma Farmhouse on Vineyard w Deck + Bocce Court

10.0 out of 10, Exceptional, (1)
"This is a really cute property just like the pictures in great shades location of successful to everything in the area."
The price is NZ$821
includes taxes & fees
15 Sept - 16 Sept
Modern Sonoma Farmhouse on Vineyard w Deck + Bocce Court
Stunning Sauna Cottage Retreat on Private Vineyard
Property grounds

Stunning Sauna Cottage Retreat on Private Vineyard

The price is NZ$874
includes taxes & fees
25 Aug - 26 Aug
Stunning Sauna Cottage Retreat on Private Vineyard
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Fridge, microwave, oven, stovetop

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

10.0 out of 10, Exceptional, (45)
"We rented this place for our babymoon and it met all of our expectations! The host is very friendly and prompt. The place was clean and had all necessities. It’s a short walk to the beach which was perfect for our pup! Hopefully we have the chance to stay here again!"
The price is NZ$1,022
includes taxes & fees
2 Sept - 3 Sept
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
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

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping

10/10 Excellent
"Best options "
Dinora 1-night trip
Posted 3 days ago
Wildhaven Sonoma Glamping

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between NZ$836 and NZ$836 per night for cottages in Healdsburg. Whatever your budget, an awesome stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Healdsburg?
Lock in your holiday dates and then choose from 24 cottages in Healdsburg. Looking for a place where you can relax and stay in touch with nature? Expedia will help you find your ideal retreat in a few quick clicks.
What is there to do in Healdsburg near my cottage?
Whatever you're interested in, Healdsburg has lots of things to keep you busy. Healdsburg Golf Club, Pezzi King Winery and Soda Rock Winery are on many visitors' sightseeing itineraries. Don't forget to explore Wilson Winery, Matrix Winery and Healdsburg Plaza either. With Expedia's Healdsburg hotel deals, you can see more awesome attractions like these with the money you save.