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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for St. Helena vacation homes

Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

1. 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 $1,867
CA $2,560 total
includes taxes & fees
Nov 1 - Nov 2
Ambrose Bierce House
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 $1,217
CA $1,683 total
includes taxes & fees
Oct 12 - Oct 13
Downtown Cottage House
A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

3. 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, (276 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 $2,423
CA $3,131 total
includes taxes & fees
Nov 1 - Nov 2
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
A bedroom with a wooden ceiling, a bed with a patterned bedspread, two bedside lamps, a rug, and a tapestry on the wall.

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 $1,097
CA $1,419 total
includes taxes & fees
Oct 6 - Oct 7
RustRidge House, two bedroom two bath home
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.

5. Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (34 reviews)
"We had a wonderful day. Thanks for the flexibility on check-in day."
United States
linda k.
The price is CA $305
CA $392 total
includes taxes & fees
Oct 6 - Oct 7
Napa Valley Retreat in Calistoga!
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, (175 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is CA $356
CA $727 total
includes taxes & fees
Oct 6 - Oct 7
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, (85 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 $356
CA $738 total
includes taxes & fees
Oct 14 - Oct 15
Glen Ellen Retreats Sunset Cottage
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, (99 reviews)
"The stay was very nice"
United States
ladonna A.
The price is CA $392
CA $771 total
includes taxes & fees
Oct 6 - Oct 7
Glen Ellen Retreats Hot Tub Cottage
A swimming pool with a slide, a barbecue area, and a wooden deck.

9. 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 $178
CA $403 total
includes taxes & fees
Oct 12 - Oct 13
2 Hidden Wine Country Gem Upstairs Unit
A terrace with wicker chairs overlooking a scenic valley.

10. The Moonlit Retreat + Casita,Bocce & Sunset Views!

The Moonlit Retreat + Casita,Bocce & Sunset Views!
Glen Ellen
9.2 out of 10, Wonderful, (17 reviews)
"My family met for a family wedding and we stayed at this wonderful property . It is a perfect distance to get away yet close enough for ease of conveyance to stores , restaurants etc . The hosts were very good communicators and made us feel totally comfortable . The place was spotlessly clean and very comfortable . Nature abounds with deer , big bunnies and birds galore . Great guest experience and we would definitely stay again when visiting the area."
United States
Alfie H.
The price is CA $685
CA $1,397 total
includes taxes & fees
Oct 11 - Oct 12
The Moonlit Retreat + Casita,Bocce & Sunset Views!
A spacious living room with a high ceiling, a large painting, and a view of the outdoors.

11. 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 $951
CA $1,739 total
includes taxes & fees
Oct 27 - Oct 28
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

12. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with 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 $442
CA $821 total
includes taxes & fees
Oct 8 - Oct 9
Wine Country Farmhouse with Hot Tub
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

13. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful stay!"
United States
Adam C.
The price is CA $449
CA $507 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Wine Country Guesthouse with Private Pool & Yard
A spacious living room with a grey sectional sofa, wooden flooring, and a wooden ceiling.

14. 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 $499
CA $1,165 total
includes taxes & fees
Oct 6 - Oct 7
Annadel House Retreat- Stunning Wine Country Luxe!
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

15. 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 $807
CA $1,959 total
includes taxes & fees
Oct 6 - Oct 7
Cloud 9 - A Retreat for Bliss and Happiness
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 $254
CA $545 total
includes taxes & fees
Oct 6 - Oct 7
Craftsman 2 blocks from Russian River Brewery!
Exterior

17. 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 $182
CA $363 total
includes taxes & fees
Oct 13 - Oct 14
Silverado Napa Luxury 1 Bed Jr. Suite
A laundry room with a washing machine, dryer, and a window with a view.

18. Napa Vineyard with Stunning Views By Allevo Homes

Napa Vineyard with Stunning Views By Allevo Homes
Napa
8.0 out of 10, Very good, (2 reviews)
"House was amazing. Great spot for us to unwind after busy days. Amazing view, pool as great. We had a great time."
United States
Matt L.
The price is CA $392
CA $1,147 total
includes taxes & fees
Oct 12 - Oct 13
Napa Vineyard with Stunning Views By Allevo Homes
Pool

19. Base Camp

Base Camp
Kenwood
The price is CA $1,733
CA $5,480 total
includes taxes & fees
Oct 7 - Oct 8
Base Camp
A two-story house with a garage, a balcony, and a driveway.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is CA $321
CA $405 total
includes taxes & fees
Oct 7 - Oct 8
King bedroom #1 Wine Country Gateway With BBQ+Billiards
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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

10/10 Excellent
"Nice and clean"
Carla 2-night trip
Posted 4 hours ago
Oxford Suites Sonoma County

Find out more about St. Helena

St. Helena Vacation Homes information

Number of reviews
1,005
Accommodation
982 Vacation Homes
Lowest Price
CA $363
Highest Price
CA $5,480

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