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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Our top choices for St. Helena holiday rentals

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, (279 reviews)
"We had an amazing stay! The house was incredibly clean, neat, and comfortable. The location is perfect- just a short 10 minute walk to Beringer Winery. The host was also super responsive whenever we had a question. Highly recommend this place!"
United States
Juri A.
The price is NZ$3,738
includes taxes & fees
29 Nov - 30 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

2. 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 NZ$912
includes taxes & fees
19 Nov - 20 Nov
RustRidge Bed and Breakfast - Rustridge Cottage

3. Napa Valley Villa Retreat - 8 bedrooms, 8 baths

Napa Valley Villa Retreat - 8 bedrooms, 8 baths
Deer Park
9.6 out of 10, Exceptional, (32 reviews)
"Dr. Roy was a wonderful host and one of the most genuinely caring owners our group has ever dealt with. He made it a point to introduce himself and offer anything he could if we needed it.The home was perfect for what our group needed. Property grounds are beautiful and rooms had plenty of space and privacy for all of us to enjoy. We were all able to make ourselves at home and loved being able to share a big space together with our friends. We'll be back next time we visit Napa."
United States
Patrick M.
The price is NZ$5,693
includes taxes & fees
23 Nov - 24 Nov
Napa Valley Villa Retreat - 8 bedrooms, 8 baths

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 NZ$1,686
includes taxes & fees
14 Nov - 15 Nov
RustRidge House, two bedroom two bath home

5. 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, (49 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 NZ$636
includes taxes & fees
19 Nov - 20 Nov
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

6. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,563 reviews)
"Great place to stay"
United States
Waldemar.
The price is NZ$272
includes taxes & fees
15 Nov - 16 Nov
RiverPointe Napa Valley Resort

7. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is NZ$623
includes taxes & fees
23 Nov - 24 Nov
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

8. Sonoma Creek Haven - Creekside Hot Tub Retreat

Sonoma Creek Haven - Creekside Hot Tub Retreat
Kenwood
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful setting and a wonderful host!"
United States
Kathryn J.
Sonoma Creek Haven - Creekside Hot Tub Retreat

9. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (46 reviews)
"A very comfortable bed and beautiful pool setting in Napa Valley!"
United States
David
The price is NZ$900
includes taxes & fees
18 Nov - 19 Nov
The Napa Residences

10. 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)
"Such a great property. Idyllic, clean and lovely interior. Nice area for breakfast and coffee, loved the bikes! Very friendly staff. Will return."
United States
Douglas F.
The price is NZ$669
includes taxes & fees
23 Nov - 24 Nov
Escape to wine country in your independent cottage in downtown Calistoga

11. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (183 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is NZ$997
includes taxes & fees
3 Dec - 4 Dec
Glen Ellen Retreats Coastal Cottage

12. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"It was clean and quiet and the host was very responsive to my needs"
United States
Debbie W.
The price is NZ$482
includes taxes & fees
16 Nov - 17 Nov
2 Hidden Wine Country Gem Upstairs Unit

13. The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
Glen Ellen
9.8 out of 10, Exceptional, (139 reviews)
"Great home, hosts, and area. We loved everything about the trip and will be back in the fall. Thank you for the wonderful experience."
United States
Robert K.
The price is NZ$924
includes taxes & fees
19 Nov - 20 Nov
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

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 NZ$1,058
includes taxes & fees
15 Nov - 16 Nov
Glen Ellen Retreats Hot Tub Cottage

15. Two-Bedroom, One Bath - Aurora House

Two-Bedroom, One Bath - Aurora House
Calistoga
9.8 out of 10, Exceptional, (36 reviews)
"We had a wonderful day. Thanks for the flexibility on check-in day."
United States
linda k.
The price is NZ$805
includes taxes & fees
15 Nov - 16 Nov
Two-Bedroom, One Bath - Aurora House

16. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (89 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 NZ$977
includes taxes & fees
6 Dec - 7 Dec
Glen Ellen Retreats Sunset Cottage

17. Fireside Sips & Oak Dreams in Sonoma Valley

Fireside Sips & Oak Dreams in Sonoma Valley
Glen Ellen
10.0 out of 10, Exceptional, (11 reviews)
"We loved our stay in Glen Ellen! The space was perfect for our family of 4! It was very well stocked! Our host was wonderful and extremely informative about the area."
United States
Kristin B.
The price is NZ$784
includes taxes & fees
15 Nov - 16 Nov
Fireside Sips & Oak Dreams in Sonoma Valley

18. 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 NZ$866
includes taxes & fees
16 Nov - 17 Nov
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

19. 2 bed I Silverado Resort & Spa in Napa - Wine Town

2 bed I Silverado Resort & Spa in Napa - Wine Town
Napa
10.0 out of 10, Exceptional, (17 reviews)
"Great value, resort is beautiful"
United States
Jack K.
The price is NZ$540
includes taxes & fees
2 Dec - 3 Dec
2 bed I Silverado Resort & Spa in Napa - Wine Town

20. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful stay!"
United States
Adam C.
The price is NZ$599
includes taxes & fees
15 Nov - 16 Nov
Cozy Wine Country Guesthouse with Private Pool & Yard
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

Find out more about St. Helena

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our St. Helena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up St. Helena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in St. Helena. Seeing all the best attractions is bound to make you fall in love with St. Helena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in St. Helena short-term rentals, that won’t be hard to do.

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.