A rustic stone building with a red door and a wooden balcony, surrounded by lush greenery and a vintage wooden cart.

St. Helena Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for St. Helena vacation homes

A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

1. Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Downtown St. Helena
10.0 out of 10, Exceptional, (278 reviews)
"Beautiful rustic property. Great for family gatherings with large kitchen and open layout. It’s very close to St. Helena downtown where you could walk ~10 mins and even right across the street from Beringer. The Host was very responsive when we were checking in and helped us resolve our user-error quickly. Our family enjoyed our brief time here, and we would consider coming back for another reunion in the future."
United States
David
The price is CA $2,398
CA $3,099 total
includes taxes & fees
Nov 1 - Nov 2
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Exterior

2. Downtown Cottage House

Downtown Cottage House
Downtown St. Helena
9.6 out of 10, Exceptional, (25 reviews)
"The location of the property is the best. "
United States
Kim B.
The price is CA $1,248
CA $1,722 total
includes taxes & fees
Nov 19 - Nov 20
Downtown Cottage House
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view of greenery outside.

3. 1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9

1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
Downtown St. Helena
10.0 out of 10, Exceptional, (286 reviews)
"Absolutely amazing location and home! Highly recommend."
United States
Cruz P.
1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

4. Ambrose Bierce House

Ambrose Bierce House
Downtown St. Helena
9.8 out of 10, Exceptional, (29 reviews)
"The innkeepers were outstanding. The facility is wonderful - easy location to enjoy St. Helena and Napa Valley."
United States
Steve H.
The price is CA $1,848
CA $2,534 total
includes taxes & fees
Nov 19 - Nov 20
Ambrose Bierce House
A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

5. Modern Organic 3BR Oasis w/ Creek&Near State Park

Modern Organic 3BR Oasis w/ Creek&Near State Park
Kenwood
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is CA $276
CA $788 total
includes taxes & fees
Oct 21 - Oct 22
Modern Organic 3BR Oasis w/ Creek&Near State Park
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

6. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (179 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is CA $354
CA $726 total
includes taxes & fees
Nov 17 - Nov 18
Glen Ellen Retreats Coastal Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

7. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (87 reviews)
"Great house and location. Very clean and comfortable. Perfect location as a base for visiting wineries. Highly recommend"
United States
patrick s.
The price is CA $354
CA $733 total
includes taxes & fees
Oct 27 - Oct 28
Glen Ellen Retreats Sunset Cottage
A swimming pool with a slide, a barbecue area, and a wooden deck.

8. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is CA $176
CA $399 total
includes taxes & fees
Oct 28 - Oct 29
2 Hidden Wine Country Gem Upstairs Unit
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

9. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (101 reviews)
"Enjoyed our stay! Walkable to restaurants, groceries, hiking trails. Well stocked kitchen for cooking. Beds and pillows extremely comfortable. The place was spotless and well maintained. Would stay here again and highly recommend!"
United States
Amy
The price is CA $389
CA $777 total
includes taxes & fees
Oct 27 - Oct 28
Glen Ellen Retreats Hot Tub Cottage
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

10. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is CA $329
CA $674 total
includes taxes & fees
Oct 21 - Oct 22
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
A bedroom with a bed, two bedside lamps, a wall art piece, and a window with blinds.

11. Wonderful Queen bedroom #2 in house with AC in charming Sonoma

Wonderful Queen bedroom #2 in house with AC in charming Sonoma
Sonoma
The price is CA $146
CA $192 total
includes taxes & fees
Oct 22 - Oct 23
Wonderful Queen bedroom #2 in house with AC in charming Sonoma
A spacious living room with a high ceiling, a large painting, and a view of the outdoors.

12. Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views

Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
Kenwood
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home & property. Great location. We thoroughly enjoyed our stay! "
United States
Laura G.
The price is CA $943
CA $1,725 total
includes taxes & fees
Oct 27 - Oct 28
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

13. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (23 reviews)
"Awesome stay. Perfect for three couples. Great support and communication from hosts and management team. Couldn’t have asked for better."
United States
Phillip T.
The price is CA $759
CA $1,934 total
includes taxes & fees
Nov 3 - Nov 4
Cloud 9 - A Retreat for Bliss and Happiness
Exterior

14. Silverado Napa Luxury 1 Bed Jr. Suite

Silverado Napa Luxury 1 Bed Jr. Suite
Napa
9.8 out of 10, Exceptional, (69 reviews)
"Spacious room with amenities nearby. Great location for visiting the wineries. Safe environment. It was a very comfortable stay. We would definitely return here again!"
United States
Tim P.
The price is CA $174
CA $351 total
includes taxes & fees
Nov 18 - Nov 19
Silverado Napa Luxury 1 Bed Jr. Suite
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

15. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful stay!"
United States
Adam C.
The price is CA $444
CA $502 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Wine Country Guesthouse with Private Pool & Yard
A spacious living area with a leather sofa, wooden coffee table, and a dining table with chairs. There are plants, bookshelves, and a kitchen in the background.

16. Craftsman 2 blocks from Russian River Brewery!

Craftsman 2 blocks from Russian River Brewery!
Santa Rosa
10.0 out of 10, Exceptional, (3 reviews)
"Very easy check in/check out"
United States
Thomas L.
The price is CA $251
CA $543 total
includes taxes & fees
Oct 22 - Oct 23
Craftsman 2 blocks from Russian River Brewery!
A backyard with a hot tub, wooden pergola, and a barbecue area.

17. Wine Country Backyard Escape

Wine Country Backyard Escape
Santa Rosa
10.0 out of 10, Exceptional, (49 reviews)
"The house was perfect for our family. We had our daughter and her husband and their two kids. The set up is extremely family friendly, and the kids loved the activities in the backyard and the games, including the video games! The location was very convenient for downtown Santa Rosa and a quick drive to wine country. All in all, a great stay."
United States
suzanne s.
The price is CA $864
CA $1,610 total
includes taxes & fees
Oct 31 - Nov 1
Wine Country Backyard Escape
Pool

18. Base Camp

Base Camp
Kenwood
The price is CA $1,567
CA $5,184 total
includes taxes & fees
Nov 10 - Nov 11
Base Camp
Private kitchen

19. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is CA $164
CA $529 total
includes taxes & fees
Nov 9 - Nov 10
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
An outdoor patio area with stone flooring, wooden tables, and wicker chairs, surrounded by lush greenery and string lights.

20. Walk to Downtown & Russian River Brewery

Walk to Downtown & Russian River Brewery
Santa Rosa
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful location, cleanliness, and has all the amenities to make for a lovely stay. "
United States
roxanne K.
The price is CA $226
CA $663 total
includes taxes & fees
Nov 2 - Nov 3
Walk to Downtown & Russian River Brewery
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 St. Helena Hotel Reviews

Sheraton Sonoma Wine Country Petaluma

Sheraton Sonoma Wine Country Petaluma

10/10 Excellent
"Great price. Nice and quiet"
Robert 1-night trip
Posted less than an hour ago
Sheraton Sonoma Wine Country Petaluma

Find out more about St. Helena

St. Helena Vacation Homes information

Number of reviews
1,318
Accommodation
986 Vacation Homes
Lowest Price
CA $192
Highest Price
CA $5,184

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