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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for St. Helena vacation homes

1. 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 $1,198
CA $1,650 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Cottage House
A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

2. 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, (274 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 $2,526
CA $3,264 total
includes taxes & fees
Oct 4 - Oct 5
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

3. 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 $1,838
CA $2,521 total
includes taxes & fees
Oct 19 - Oct 20
Ambrose Bierce House
A spacious living area with a fireplace, a large bookshelf, and a view of the outdoors.

4. RustRidge House, two bedroom two bath home

RustRidge House, two bedroom two bath home
St Helena
10.0 out of 10, Exceptional, (2 reviews)
"Easy to find and nice and quiet. "
United States
Kristen F.
The price is CA $1,081
CA $1,320 total
includes taxes & fees
Sep 28 - Sep 29
RustRidge House, two bedroom two bath home
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
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is CA $275
CA $781 total
includes taxes & fees
Sep 28 - Sep 29
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, (173 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is CA $351
CA $727 total
includes taxes & fees
Sep 28 - Sep 29
Glen Ellen Retreats Coastal Cottage
A swimming pool with a slide, a barbecue area, and a wooden deck.

7. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (30 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 $164
CA $383 total
includes taxes & fees
Oct 4 - Oct 5
2 Hidden Wine Country Gem Upstairs Unit
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

8. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (96 reviews)
"The stay was very nice"
United States
ladonna A.
The price is CA $386
CA $771 total
includes taxes & fees
Sep 28 - Sep 29
Glen Ellen Retreats Hot Tub Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

9. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (84 reviews)
"Lovely, clean home in great location. Beautiful back yard. Great host. We loved our stay and plan to return!"
United States
Michelle W.
The price is CA $351
CA $727 total
includes taxes & fees
Oct 19 - Oct 20
Glen Ellen Retreats Sunset Cottage
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

10. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 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 $407
CA $777 total
includes taxes & fees
Sep 24 - Sep 25
Wine Country Farmhouse with Hot Tub
A two-story house with a garage, a balcony, and a driveway.

11. King bedroom #1 Wine Country Gateway With BBQ+Billiards

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is CA $316
CA $399 total
includes taxes & fees
Oct 1 - Oct 2
King bedroom #1 Wine Country Gateway With BBQ+Billiards
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

12. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Adam C.
The price is CA $442
CA $505 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Wine Country Guesthouse with Private Pool & Yard
A spacious living room with a grey sectional sofa, wooden flooring, and a wooden ceiling.

13. Annadel House Retreat- Stunning Wine Country Luxe!

Annadel House Retreat- Stunning Wine Country Luxe!
Santa Rosa
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay, nice views"
United States
Robert B.
The price is CA $418
CA $1,068 total
includes taxes & fees
Sep 27 - Sep 28
Annadel House Retreat- Stunning Wine Country Luxe!
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.

14. 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 $548 total
includes taxes & fees
Sep 30 - Oct 1
Craftsman 2 blocks from Russian River Brewery!
An outdoor patio area with stone flooring, wooden tables, and wicker chairs, surrounded by lush greenery and string lights.

15. Walk to Downtown & Russian River Brewery

Walk to Downtown & Russian River Brewery
Santa Rosa
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful location, cleanliness, and has all the amenities to make for a lovely stay. "
United States
roxanne K.
The price is CA $229
CA $663 total
includes taxes & fees
Sep 28 - Sep 29
Walk to Downtown & Russian River Brewery

16. 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 $165
CA $527 total
includes taxes & fees
Sep 29 - Sep 30
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A spacious living room with a high ceiling, a large painting, and a view of the outdoors.

17. 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 $994
CA $1,761 total
includes taxes & fees
Oct 5 - Oct 6
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
A living room with a red sofa, a green armchair, and a red armchair with patterned cushions. There is a coffee table with books and a lamp. The room has wooden flooring and a large window with blinds.

18. Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (34 reviews)
"This cozy place was exactly as pictured and spotless. Communication with the owners was easy and responsive. We really enjoyed our stay and would happily return."
United States
Summer S.
The price is CA $561
CA $723 total
includes taxes & fees
Sep 27 - Sep 28
Napa Valley Retreat in Calistoga!
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

19. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is CA $232
CA $523 total
includes taxes & fees
Oct 12 - Oct 13
Wine Country Cottage Escape
A house with a patio area featuring outdoor furniture and a stone pathway.

20. Private 1+ acre, Bocce, Waterfall, Free Pool Heat

Private 1+ acre, Bocce, Waterfall, Free Pool Heat
Santa Rosa
9.8 out of 10, Exceptional, (20 reviews)
"This house was wonderful for a family gathering. The private yard itself added so many beautiful places to play games and congregate, and we spent most of our time outside. All amenities were provided, and the host checked in a few times to make sure everything was going well. The location near the wineries and other destinations was also excellent. We would most definitely stay here again."
United States
Polly B.
The price is CA $725
CA $1,537 total
includes taxes & fees
Sep 27 - Sep 28
Private 1+ acre, Bocce, Waterfall, Free Pool Heat
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

Harvest Inn

Harvest Inn

10/10 Excellent
"Beautiful, large room with a fireplace. High ceiling made it feel even larger. Bathroom was also large! We will definitely stay here again!"
Donald 1-night trip
Posted 11 hours ago
Harvest Inn

Find out more about St. Helena

St. Helena Vacation Homes information

Number of reviews
606
Accommodation
981 Vacation Homes
Lowest Price
CA $383
Highest Price
CA $3,264

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