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
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 rentals

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 HK$6,997
HK$9,655 total
includes taxes & fees
19 Nov - 20 Nov
Downtown Cottage House
Property grounds

2. 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$2,482
HK$3,411 total
includes taxes & fees
2 Nov - 3 Nov
Spacious Honeymoon Suite
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view of greenery outside.

3. 1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9

1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
Downtown St. Helena
10.0 out of 10, Exceptional, (286 reviews)
"Absolutely amazing location and home! Highly recommend."
United States
Cruz P.
The price is HK$9,810
HK$14,703 total
includes taxes & fees
20 Oct - 21 Oct
1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
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, (277 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$13,342
HK$17,242 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$4,186 total
includes taxes & fees
20 Oct - 21 Oct
RustRidge Bed and Breakfast - Rustridge Cottage
Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

6. 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$10,281
HK$14,099 total
includes taxes & fees
19 Nov - 20 Nov
Ambrose Bierce House
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, (47 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is HK$2,739
HK$3,756 total
includes taxes & fees
20 Oct - 21 Oct
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A room with a brown sofa, two wicker chairs, a small table with a lamp, and a framed picture on the wall.

8. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
The price is HK$1,766
HK$2,031 total
includes taxes & fees
20 Oct - 21 Oct
Hideaway Cottages
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

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

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 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$2,739
HK$3,756 total
includes taxes & fees
20 Oct - 21 Oct
Escape to wine country in your independent cottage in downtown Calistoga
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.

10. 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$2,087
HK$3,558 total
includes taxes & fees
23 Oct - 24 Oct
Sonoma Stonehouse, Wine Country Vibes
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

11. 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 HK$1,962
HK$4,043 total
includes taxes & fees
20 Oct - 21 Oct
Glen Ellen Retreats Coastal Cottage
A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

12. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,535 reviews)
"Great place to stay"
United States
Waldemar.
The price is HK$749
HK$1,132 total
includes taxes & fees
20 Oct - 21 Oct
RiverPointe Napa Valley Resort
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

13. 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$384
HK$3,954 total
includes taxes & fees
4 Nov - 5 Nov
The Napa Residences
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

14. 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 HK$2,158
HK$4,287 total
includes taxes & fees
20 Oct - 21 Oct
Glen Ellen Retreats Hot Tub Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

15. 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 HK$1,962
HK$4,043 total
includes taxes & fees
20 Oct - 21 Oct
Glen Ellen Retreats Sunset Cottage
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

16. 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 HK$1,829
HK$3,775 total
includes taxes & fees
20 Oct - 21 Oct
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

17. 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$4,213
HK$10,733 total
includes taxes & fees
3 Nov - 4 Nov
Cloud 9 - A Retreat for Bliss and Happiness
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

18. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful stay!"
United States
Adam C.
The price is HK$2,472
HK$2,794 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Wine Country Guesthouse with Private Pool & Yard
A backyard with a hot tub, wooden pergola, and a barbecue area.

19. Wine Country Backyard Escape

Wine Country Backyard Escape
Santa Rosa
10.0 out of 10, Exceptional, (49 reviews)
"The house was perfect for our family. We had our daughter and her husband and their two kids. The set up is extremely family friendly, and the kids loved the activities in the backyard and the games, including the video games! The location was very convenient for downtown Santa Rosa and a quick drive to wine country. All in all, a great stay."
United States
suzanne s.
Wine Country Backyard Escape
A swimming pool with a slide, a barbecue area, and a wooden deck.

20. 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 HK$982
HK$2,197 total
includes taxes & fees
25 Oct - 26 Oct
2 Hidden Wine Country Gem Upstairs Unit
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

Elm House Inn

Elm House Inn

8/10 Good
"A very cute little BnB! The breakfast was great and the staff was so friendly and helpful"
Liz 2-night trip
Posted 14 hours ago
Elm House Inn

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.