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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for St. Helena vacation homes

Exterior

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 $1,210
CA $1,674 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.

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 $2,546
CA $3,289 total
includes taxes & fees
Oct 20 - Oct 21
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 $1,915
CA $2,619 total
includes taxes & fees
Oct 4 - Oct 5
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 $1,089
CA $1,408 total
includes taxes & fees
Oct 2 - Oct 3
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, (4 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is CA $277
CA $789 total
includes taxes & fees
Sep 30 - Oct 1
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, (174 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is CA $354
CA $733 total
includes taxes & fees
Oct 20 - Oct 21
Glen Ellen Retreats Coastal Cottage
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.

7. 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 $303
CA $390 total
includes taxes & fees
Sep 30 - Oct 1
Napa Valley Retreat in Calistoga!
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 $166
CA $384 total
includes taxes & fees
Oct 4 - Oct 5
2 Hidden Wine Country Gem Upstairs Unit
A two-story house with a garage, a balcony, and a driveway.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is CA $318
CA $399 total
includes taxes & fees
Oct 2 - Oct 3
King bedroom #1 Wine Country Gateway With BBQ+Billiards
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

10. 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 $354
CA $733 total
includes taxes & fees
Oct 20 - Oct 21
Glen Ellen Retreats Sunset Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

11. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (97 reviews)
"The stay was very nice"
United States
ladonna A.
The price is CA $389
CA $777 total
includes taxes & fees
Oct 20 - Oct 21
Glen Ellen Retreats Hot Tub Cottage
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 $447
CA $502 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Wine Country Guesthouse with Private Pool & Yard
Private kitchen

13. 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 $149
CA $502 total
includes taxes & fees
Sep 30 - Oct 1
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

14. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is CA $233
CA $526 total
includes taxes & fees
Oct 26 - Oct 27
Wine Country Cottage Escape
A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

15. Charming Wine Country Home w/Hot Tub near Downtown

Charming Wine Country Home w/Hot Tub near Downtown
Santa Rosa
9.6 out of 10, Exceptional, (20 reviews)
"Loved this place. Everything was labeled making the house easy to find things."
United States
Joel B.
The price is CA $270
CA $700 total
includes taxes & fees
Sep 30 - Oct 1
Charming Wine Country Home w/Hot Tub near Downtown
A spacious kitchen with a large island, a dining area with a sofa and chairs, and a view of the outdoors.

16. Silverado Napa Breath Taking Remodel 3 bed 2 bath

Silverado Napa Breath Taking Remodel 3 bed 2 bath
Napa
9.8 out of 10, Exceptional, (14 reviews)
"Clean and pet friendly place"
United States
Tracie T.
The price is CA $260
CA $611 total
includes taxes & fees
Sep 30 - Oct 1
Silverado Napa Breath Taking Remodel 3 bed 2 bath
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

17. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location!"
United States
Riley F.
The price is CA $230
CA $555 total
includes taxes & fees
Sep 30 - Oct 1
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

18. 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 $468
CA $846 total
includes taxes & fees
Oct 4 - Oct 5
Wine Country Farmhouse with Hot Tub
A terrace with wicker chairs overlooking a scenic valley.

19. 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 $682
CA $1,390 total
includes taxes & fees
Oct 11 - Oct 12
The Moonlit Retreat + Casita,Bocce & Sunset Views!
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.

20. 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 $253
CA $542 total
includes taxes & fees
Oct 1 - Oct 2
Craftsman 2 blocks from 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

Archer Hotel Napa

Archer Hotel Napa

10/10 Excellent
"Love this hotel! My husband and I stayed here for our anniversary and had such a wonderful experience. When we arrived, champagne and chocolate-covered strawberries were waiting for us in our room. We also enjoyed a couples massage at the spa and spent time relaxing at the rooftop. The second night, we came back to find confetti and a sweet “Happy Anniversary” note from housekeeping. It was little touches like this that made our stay feel extra special. The location is perfect—right in the middle of all the restaurants and bars and within walking distance of the river. The staff was incredibly friendly and welcoming. We had such a great experience and would definitely stay here again. Highly recommend!"
neda 2-night trip
Posted 14 hours ago
Archer Hotel Napa

Find out more about St. Helena

St. Helena Vacation Homes information

Number of reviews
568
Accommodation
982 Vacation Homes
Lowest Price
CA $384
Highest Price
CA $3,289

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