We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Sign in
to get trip updates and message other travellers.
Healdsburg
Healdsburg Tourism
Healdsburg Accommodation
Healdsburg Bed and Breakfast
Healdsburg Holiday Rentals
Healdsburg Holiday Packages
Healdsburg Flights
Healdsburg Restaurants
Healdsburg Attractions
Healdsburg Travel Forum
Healdsburg Photos
Healdsburg Map
Healdsburg Guide
Hotels
All Healdsburg Hotels
Healdsburg Hotel Deals
Last Minute Hotels in Healdsburg
By Hotel Type
By Hotel Class
By Hotel Brand
Popular Amenities
Popular Healdsburg Categories
Near Airports
Healdsburg Motels
Family Hotels Healdsburg
Spa Resorts Healdsburg
Business Hotels Healdsburg
Romantic Hotels Healdsburg
Healdsburg Green Hotels
Luxury Hotels Healdsburg
Healdsburg Beach Hotels
5-stars Hotels in Healdsburg
4-stars Hotels in Healdsburg
3-stars Hotels in Healdsburg
Relais & Châteaux Hotels in Healdsburg
Healdsburg Hotels with a Pool
Pet Friendly Hotels in Healdsburg
Healdsburg Cheap Pet Friendly Hotels
Healdsburg Hot Tub Suite Hotels
Healdsburg Pet Friendly Campsites
Design Hotels in Healdsburg
Clean Hotels in Healdsburg
Downtown Bed and Breakfast in Healdsburg
Hotels with Complimentary Breakfast in Healdsburg
Luxury Spa Hotels in Healdsburg
Spa Hotels Healdsburg
Hotels with Kitchenette in Healdsburg
Hotels near (SMF) Sacramento Intl Airport
Hotels near (STS) Sonoma County Airport
Things to do
Restaurants
Flights
Holiday Rentals
By Holiday Rental Type
Places of Interest
Cheap Healdsburg Holiday Rentals
Holiday Rentals near Simi Winery
Holiday Rentals near Alexander Valley Vineyards
Holiday Rentals near Francis Ford Coppola Winery
Holiday Rentals near Chalk Hill Winery
Holiday Rentals near Copain Wines
Shopping
Package Holidays
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Best of 2022
Help Centre
Travel Articles
Healdsburg, CA Cottages, Apartment Rentals and Holiday Rentals
Holiday Rentals
USA
California (CA)
Sonoma County
Healdsburg Cottages
Search
Cottages in Healdsburg
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Parking (87)
Internet (86)
Other outdoor space (82)
Air Conditioning (78)
Show more
Suitability
Kid friendly (70)
Wheelchair access (6)
Elder access (3)
Business Travel (3)
Show more
Property type
Holiday Rental House (90)
Condominium/Apartment (2)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Mountain Views (5)
Housekeeping Included (3)
Boat Available (1)
Private Chef (0)
Show more
Distance from
1 km
92 rentals
in Healdsburg.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order.
Learn more.
Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.
199 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Healdsburg - Chalk Hill Wine Country Cottage
174 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
136 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Wooded Restful Retreat, with broad scenic views, outdoor dining
203 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Hilltop Hideaway: Bright, Fresh, Modern, Views And Only 2 Miles To Plaza
122 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Healdsburg River Front Oasis Retreat.
94 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Secluded Valley Retreat
80 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views)
94 reviews
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly
110 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Healdsburg Cottage Walk to the Plaza, Workspace
147 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Save time - get the best
Healdsburg
rentals sent straight to your email!
Get the List
Tanda Tula, Wine Country Sanctuary
104 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
47 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
114 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Superb Healdsburg Location, Spectacular Views, Minutes to Town
39 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Beautiful Studio Getaway in the Heart of Wine Country
64 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views
147 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool
40 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Modern, newly built 5 BR home with beautiful views and 50 acres of privacy
29 reviews
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Dry Creek Cottage - Healdsburg
86 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS
59 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Modern Sophisticated Private Luxurious W/Views & Hot Tub
169 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome
38 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza
37 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg
160 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!
90 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!
68 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.
22 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
luxuriously appointed new large guest suite in a landmark Victorian
49 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.
31 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Updated cabin, right on Russian River, amazing views & location!
31 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Dog Friendly Vineyard Estate Cottage with Lap Pool and Incredible Views
46 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
82 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly
116 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Creek Front Vineyard, West Dry Creek Healdsburg CA
27 reviews
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Bunkhouse at Side Road Farm charming one bedroom cottage
29 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza
22 reviews
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Beautiful Views! Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg
65 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball
82 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
New Contemporary Home in the Heart of Sonoma Wine Country.
30 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)
44 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Dry Creek Valley Home and Vineyard
39 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
*LImited Time Discount* Healdsburg Riverside Cottage - Beautiful River Views
34 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza
36 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Rendezvous Under the Oaks-Pool & hot Spa
29 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
VineHaven- Spa, Gardens, & Spectacular Vineyard Views
53 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Vineyard Guest House
17 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers
21 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa
36 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Private 3 Bed + Cottage Wine Country Estate With Pool And More
32 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
52 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Previous
Next
1
2
Frequently Asked Questions about Healdsburg
Do any holiday rentals in Healdsburg have a pool?
Yes, here are some popular holiday rentals in Healdsburg that have a pool:\n
\n
Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games
\n
Tanda Tula, Wine Country Sanctuary
\n
Secluded Valley Retreat
\n
\n
See all holiday rentals with a pool in Healdsburg on Tripadvisor
Do any holiday rentals in Healdsburg have internet access?
Yes, here are some popular holiday rentals in Healdsburg that have internet access:\n
\n
Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens
\n
Kenya's Kastle
\n
Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views
\n
\n
See all holiday rentals in Healdsburg on Tripadvisor
What are the best pet friendly rentals in Healdsburg?
The best pet friendly rentals in Healdsburg are:\n
\n
Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens
\n
Kenya's Kastle
\n
Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views
\n
\n
See all pet friendly holiday rentals in Healdsburg on Tripadvisor
What are some great rentals in Healdsburg that are kid friendly?
Some of the most popular kid friendly rentals in Healdsburg are:\n
\n
Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens
\n
Kenya's Kastle
\n
Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views
\n
\n
See all kid friendly holiday rentals in Healdsburg on Tripadvisor