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

Holiday Homes in St. Helena

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Check prices for these dates

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

Our top choices for St. Helena holiday 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 €1,955
includes taxes & fees
1 Nov - 2 Nov
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 €1,298
includes taxes & fees
23 Nov - 24 Nov
Downtown Cottage House
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.
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.

4. 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.
Modern Organic 3BR Oasis w/ Creek&Near State Park
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

5. 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 €500
includes taxes & fees
25 Oct - 26 Oct
Glen Ellen Retreats Sunset Cottage
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 €500
includes taxes & fees
25 Oct - 26 Oct
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, (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 €255
includes taxes & fees
25 Oct - 26 Oct
2 Hidden Wine Country Gem Upstairs Unit
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

8. 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 €435
includes taxes & fees
27 Oct - 28 Oct
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
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 €532
includes taxes & fees
25 Oct - 26 Oct
Glen Ellen Retreats Hot Tub Cottage
A spacious living room with a high ceiling, a large painting, and a view of the outdoors.

10. 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 €1,095
includes taxes & fees
27 Oct - 28 Oct
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
A bathroom with two sinks, a mirror, and a towel rack.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is €256
includes taxes & fees
25 Oct - 26 Oct
King bedroom #1 Wine Country Gateway With BBQ+Billiards
A bedroom with a bed, two bedside lamps, a wall art piece, and a window with blinds.

12. 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 €206
includes taxes & fees
3 Nov - 4 Nov
Wonderful Queen bedroom #2 in house with AC in charming Sonoma
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, (37 reviews)
"Wonderful stay!"
United States
Adam C.
The price is €324
includes taxes & fees
29 Oct - 30 Oct
Cozy Wine Country Guesthouse with Private Pool & Yard
A bedroom with a bed, bedside lamps, a rug, a window, and a chair.

14. Delightful King Bedroom #3 in house with AC in charming Sonoma

Delightful King Bedroom #3 in house with AC in charming Sonoma
Sonoma
The price is €240
includes taxes & fees
2 Nov - 3 Nov
Delightful King Bedroom #3 in house with AC in charming Sonoma
A bathroom with a sink, toilet, and bathtub.

15. Wine Country Harvest Vacation Home

Wine Country Harvest Vacation Home
Scenic Brush Creek
9.8 out of 10, Exceptional, (109 reviews)
"Absolutely beautiful home!!! My family and myself were so impressed!! The backyard was stunning and we spent a lot of time out there!! The home was updated, huge, with more than adequate bedrooms and bathrooms. The main bathroom has the biggest countertop I have ever seen in a vacation rental. I was in heaven!! I had room to spread out and sort all my makeup, cleansers, etc. We will definitely stay there again!!"
United States
David E.
Wine Country Harvest Vacation Home
Exterior

16. 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 €212
includes taxes & fees
18 Nov - 19 Nov
Silverado Napa Luxury 1 Bed Jr. Suite
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.

17. 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 €350
includes taxes & fees
25 Oct - 26 Oct
Craftsman 2 blocks from Russian River Brewery!
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

18. 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 €1,347
includes taxes & fees
9 Nov - 10 Nov
Cloud 9 - A Retreat for Bliss and Happiness
A modern kitchen with a central island, dining area with chairs, and a view of the outdoors.

19. Spacious 5BR/3BA Group Getaway, Pool & EV Charger

Spacious 5BR/3BA Group Getaway, Pool & EV Charger
Santa Rosa
10.0 out of 10, Exceptional, (13 reviews)
"This was a perfect place for our group. The home is beyond beautiful and felt very clean and homey. I would absolutely recommend this stay!"
United States
shea o.
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
Pool

20. Base Camp

Base Camp
Kenwood
The price is €3,523
includes taxes & fees
10 Nov - 11 Nov
Base Camp
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

Napa Winery Inn

Napa Winery Inn

10/10 Excellent
"All around lovely hotel. I would recommend without hesitation."
Courtney 1-night trip
Posted 2 hours ago
Napa Winery Inn

Find out more about St. Helena

St. Helena Holiday Homes information

Number of reviews
1,060
Accommodation
979 Holiday Homes
Lowest Price
€206
Highest Price
€3,523