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

St. Helena Holiday Rentals

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Check prices for these dates

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

Our top choices for St. Helena holiday rentals

Property grounds

1. Spacious Honeymoon Suite

Spacious Honeymoon Suite
Downtown St. Helena
10.0 out of 10, Exceptional, (23 reviews)
"Great location, clean, and quiet. We could walk to several great restaurants! "
United States
Cheryl Z.
The price is HK$2,481
HK$3,410 total
includes taxes & fees
14 Oct - 15 Oct
Spacious Honeymoon Suite
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 HK$6,867
HK$9,341 total
includes taxes & fees
13 Oct - 14 Oct
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.
The price is HK$10,279
HK$13,821 total
includes taxes & fees
1 Nov - 2 Nov
Ambrose Bierce House
A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

4. 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 HK$13,339
HK$17,097 total
includes taxes & fees
1 Nov - 2 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
A wooden deck with a round table and two chairs, surrounded by a metal railing, overlooking a forested area.

5. RustRidge Bed and Breakfast - Rustridge Cottage

RustRidge Bed and Breakfast - Rustridge Cottage
St Helena
8.0 out of 10, Very good, (3 reviews)
"We had a magical time. The horses, pool, Vinyard and hospitality was wonderful. What a special ranch. Oh and the breakfast! Delicious!!"
United States
ila m.
The price is HK$3,237
HK$4,185 total
includes taxes & fees
11 Oct - 12 Oct
RustRidge Bed and Breakfast - Rustridge Cottage
A spacious living area with a fireplace, a large bookshelf, and a view of the outdoors.

6. 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 HK$6,042
HK$7,811 total
includes taxes & fees
2 Oct - 3 Oct
RustRidge House, two bedroom two bath home
A small, single-story house with a front porch, a chimney, and a door with a window above it.

7. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (45 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is HK$2,660
HK$3,651 total
includes taxes & fees
5 Oct - 6 Oct
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A spacious lobby with a large sofa, a coffee table, and a leather armchair. A fireplace is visible in the background, and there is a staircase leading to an upper level.

8. Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
9.0 out of 10, Wonderful, (2 reviews)
"What a lovely place to stay! Seamless check in and check out. Host answered every question quickly. Other rooms/guests were never heard entering or exiting. Clean and comfy."
United States
Tresa
The price is HK$2,969
HK$4,582 total
includes taxes & fees
23 Oct - 24 Oct
Sonoma Stonehouse, Wine Country Vibes
An outdoor seating area with a table, candles, and a potted plant.

9. Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is HK$1,483
HK$1,894 total
includes taxes & fees
1 Nov - 2 Nov
Comfort and Style in Our Queen Cottage
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 HK$3,772
HK$7,402 total
includes taxes & fees
11 Oct - 12 Oct
The Moonlit Retreat + Casita,Bocce & Sunset Views!
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

11. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (6 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is HK$2,424
HK$3,322 total
includes taxes & fees
6 Oct - 7 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

12. 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 HK$1,962
HK$4,019 total
includes taxes & fees
6 Oct - 7 Oct
Glen Ellen Retreats Coastal Cottage
A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

13. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,511 reviews)
"Great place to stay"
United States
Waldemar.
The price is HK$817
HK$1,210 total
includes taxes & fees
1 Nov - 2 Nov
RiverPointe Napa Valley Resort
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.

14. 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 HK$1,679
HK$2,151 total
includes taxes & fees
6 Oct - 7 Oct
Napa Valley Retreat in Calistoga!
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

15. 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 HK$2,707
HK$4,852 total
includes taxes & fees
4 Oct - 5 Oct
Wine Country Farmhouse with Hot Tub
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

16. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (98 reviews)
"The stay was very nice"
United States
ladonna A.
The price is HK$2,158
HK$4,262 total
includes taxes & fees
6 Oct - 7 Oct
Glen Ellen Retreats Hot Tub Cottage
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

17. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (43 reviews)
"Nice, great location."
United States
Juan
The price is HK$469
HK$4,128 total
includes taxes & fees
1 Nov - 2 Nov
The Napa Residences
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

18. 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 HK$1,962
HK$4,042 total
includes taxes & fees
19 Oct - 20 Oct
Glen Ellen Retreats Sunset Cottage
A large, single-story building with a symmetrical facade, surrounded by a well-maintained lawn and palm trees.

19. 2BR Napa Getaway Side-by-side Condos Golf View

2BR Napa Getaway Side-by-side Condos Golf View
4.0 star property
Napa
The price is HK$3,327
HK$8,847 total
includes taxes & fees
1 Nov - 2 Nov
2BR Napa Getaway Side-by-side Condos Golf View
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

20. 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 HK$4,558
HK$11,089 total
includes taxes & fees
6 Oct - 7 Oct
Cloud 9 - A Retreat for Bliss and Happiness
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
"Surrounded by hiking trails, Meadowlands, and River scenery, to Sheraton hotel is one of the more extraordinary experiences you could have in Petaluma."
rowland h. 2-night trip
Posted 6 hours ago
Sheraton Sonoma Wine Country Petaluma

Find out more about St. Helena

Search for holiday rentals in St. Helena on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Helena using one of the methods below:

  • View our selection of featured holiday rentals in St. Helena
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  • Enter your travel dates to view the best deals on holiday rentals in St. Helena while they last

Look no further and take a look at our great range of rental properties in St. Helena!

Frequently asked questions

Can I find holiday rentals in St. Helena?

Yes, there are holiday rentals close to the most popular sights in St. Helena, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say St. Helena has a good selection of wineries and top-notch restaurants. Leave some time to check out the shops and spas during your trip.

What are some of the best holiday rentals that St. Helena has to offer?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This highly rated holiday home rental in St. Helena is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in St. Helena?

Expedia has 64 holiday rentals for your stay in St. Helena.

What can I see and do in St. Helena?

Cultural attractions include The Christopher Hill Gallery and Cameo Cinema, whereas Napa River is one spot to enjoy nature. Beringer Vineyards and Charles Krug Winery are other places to visit while you're in town.

What are holiday rentals like in St. Helena?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in St. Helena. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.