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Browse Select St. Helena Holiday Homes

Newly renovated Tuscan guest house on secluded private vineyard
Situated in the mountains, this holiday home is 0.4 mi (0.7 km) from Bothe-Napa State Park and within 6 miles (10 km) of Sugarloaf Ridge State Park and Beringer ...
4.9/5Exceptional! (78 reviews)
Great Views!
"Property was fantastic. Cottage was very clean and host was great. She gave so many wonderful recommendations. Property has great views and it was a peaceful stay. Would recommend."

Reviewed on 15 Sep 2021

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Newly renovated Tuscan guest house on secluded private vineyard
683 S At Silverado Studio Bedroom Residence
3.5 out of 5
683 Cottage Drive, Napa, CA
Situated in Napa, this holiday home is 2.5 mi (4 km) from Black Stallion Winery and 3 mi (4.9 km) from Darioush Winery. Oxbow Public Market and Scientopia Discovery ...
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683 S At Silverado Studio Bedroom Residence
Charming Farmhouse With Multiple Patios, Fire pit & Outdoor Dining
Situated in Santa Rosa, this holiday home is within 3 miles (5 km) of Main Stage West, Palm Drive Hospital and Luther Burbank's Experiment Farm. Sonoma County ...
5/5Exceptional! (15 reviews)
GRAND COTTAGE
"A beautiful, peaceful abode, with space inside and outside for everyone to enjoy, together and apart. Feels very grand and special."

Reviewed on 6 Sep 2021

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Charming Farmhouse With Multiple Patios, Fire pit & Outdoor Dining
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1BD 1BA Wine Country Bungalow hosted by winemaker
Situated in Santa Rosa, this holiday home is within 3 miles (5 km) of Charles M. Schulz Museum, Redwood Empire Ice Arena and Empire College. Kendall-Jackson ...
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1BD 1BA Wine Country Bungalow hosted by winemaker
1725 Elm Street 3Bed 3Bath Accommodation
The price is £1,071 per night from 18 Oct to 18 Oct
Situated in Napa, this holiday home is 0.7 mi (1.1 km) from Uptown Theater and 2.2 mi (3.5 km) from Napa Valley College. JaM Cellars and Riverbend Plaza are ...
1725 Elm Street 3Bed 3Bath Accommodation
Sonoma's Best Cottages
3.5 out of 5
1190 E Napa St, Sonoma, CA
Fully refundableReserve now, pay when you stay
The price is £220 per night from 18 Oct to 18 Oct
Situated in Sonoma, this holiday home is within 1 mile (2 km) of Sonoma State Historic Park, Buena Vista Winery and Bartholomew Park Winery. Sebastiani Theatre ...
4.8/5Exceptional! (9 reviews)
"Overall a good experience: beautiful surrounding area, conveniently located"

Reviewed on 7 Aug 2021

Sonoma's Best Cottages
Luxury Historic Mansion: 9 Bedrooms, Year-Round Heated Pool
The price is £3,270 per night from 17 Oct to 17 Oct
Situated in Santa Rosa, this historic holiday home is within 3 miles (5 km) of Sonoma County Fairgrounds, Santa Rosa Junior College and Luther Burbank Home and ...
5/5Exceptional! (6 reviews)
Great location for a family reunion
"The location, house, and setting were perfect for our family reunion. We were able to enjoy activities together and/or seek privacy when desired. Our ages were from 4-100 years! One caution - there are multiple levels and stairs which could be a challenge for anyone with limited mobility. Otherwise, ..."

Reviewed on 4 Sep 2021

Luxury Historic Mansion: 9 Bedrooms, Year-Round Heated Pool
4 BD/3 BA WINE COUNTRY HOME | MINS FROM DOWNTOWN SANTA ROSA
The price is £528 per night from 27 Sep to 27 Sep
Located in Junior College Neighborhood Association, this holiday home is within a 15-minute walk of Santa Rosa Memorial Hospital and St. Joseph Health - Sonoma ...
5/5Exceptional! (2 reviews)
Cute house near downtown SR
"Had a wonderful time. Everything was as listed. Clean, and convenient location. Only improvement would be to have to more kitchen items. We needed a colander, bigger serving bowls, and a kettle or hot water heater. Presumably if you’re renting a big house like this you’re going to be cooking for ..."

Reviewed on 14 Sep 2021

4 BD/3 BA WINE COUNTRY HOME | MINS FROM DOWNTOWN SANTA ROSA
West End Cottage with King Bed
152 W 8th St, Cottage, Santa Rosa, CA
The price is £214 per night from 28 Sep to 28 Sep
Located in the heart of Santa Rosa, this holiday home is within a 10-minute walk of Railroad Square Historic District and California Welcome Center. Sonoma County ...
5/5Exceptional! (17 reviews)
Lovely Cottage that felt like home!
"I loved staying here--it was so perfectly decorated with all the amenities I could need. Thoughtfully designed, quiet and clean."

Reviewed on 27 Jul 2021

West End Cottage with King Bed
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
The price is £1,563 per night from 27 Sep to 27 Sep
This family-friendly Sonoma holiday home is within 3 mi (5 km) of Sonoma Golf Club and Sonoma Plaza. Vallejo Home and Lachryma Montis are also within 3 miles ...
4.8/5Exceptional! (101 reviews)
Very relaxing
"The house and garden were great to hang out in and the kitchen had everything we needed."

Reviewed on 6 Sep 2021

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Napa Valley Hideaway; Quiet Setting in St. Helena, the Heart of the Wine Country
This family-friendly St. Helena holiday home is located in a rural location, within a 10-minute walk of Christopher Hill Gallery and The Christopher Hill Gallery. ...
4.8/5Exceptional! (38 reviews)
Great getaway to start my 50's!
"We enjoyed our stay in St. Helena very much! House is super fun and the yard around it is very cool and enjoyable. It is walking distance to restaurants, coffee shops, shopping, etc. We walked to Goose and Gander for dinner one night and drinks another and loved it! Definately would recommend for ..."

Reviewed on 19 Aug 2021

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Napa Valley Hideaway; Quiet Setting in St. Helena, the Heart of the Wine Country
Gorgeous Glen Ellen Home w/ Spa, Decks & Office
2467 Warm Springs Road, Glen Ellen, CA
Situated in Glen Ellen, this holiday home is 0.8 mi (1.3 km) from Morton's Warm Springs and within 3 miles (5 km) of VJB Vineyard & Cellars and Trione-Annadel ...
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Gorgeous Glen Ellen Home w/ Spa, Decks & Office
The Corner Cottage ~ Downtown out your door with Private Vineyard
Located in Downtown Napa, this historic holiday home is within a 10-minute walk of Napa Opera House, Napa Valley Wine Train, and Oxbow Public Market. Downtown ...
4.9/5Exceptional! (68 reviews)
Great Property in Perfect Downtown Location
"We loved our stay in this property. The location is premium in downtown. Susan is delightful, warm, and welcoming. She went above and beyond with clear communication, a beautiful home and vineyard, and all of the extras you could ever ask for in the home. I would highly recommend this rental and ..."

Reviewed on 9 Sep 2021

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The Corner Cottage ~ Downtown out your door with Private Vineyard
La Vino Loft in the Heart of Downtown Napa
Located in the heart of Napa, this holiday home is 0.4 mi (0.7 km) from Uptown Theater and 2.2 mi (3.5 km) from Napa Valley College. Riverbend Plaza and JaM ...
4.7/5Exceptional! (15 reviews)
Beautiful and clean property!
"The place was even better than in pictures! Each room was a great place to stay, with all three king beds being super comfortable. The host left us an amazing collection of goodies from Trader Joe’s, which came in handy in between our wine tastings! The kitchen had everything we needed, and the house ..."

Reviewed on 26 Aug 2021

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La Vino Loft in the Heart of Downtown Napa
1br/1ba Silverado Studio W/ Pool & Private Patio Studio Bedroom Condo
3.5 out of 5
1600 Atlas Peak Rd, Unit 272, Napa, CA
Situated in Napa, this golf holiday home is 2.4 mi (3.8 km) from Black Stallion Winery and 2.9 mi (4.7 km) from Darioush Winery. Napa Valley College and Oxbow ...
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1br/1ba Silverado Studio W/ Pool & Private Patio Studio Bedroom Condo
The Dalya Estate- features 2 renovated homes, located on a small vineyard estate
Situated in Sebastopol, this romantic holiday home is 0.6 mi (0.9 km) from Russian River Vineyard and within 3 miles (5 km) of Iron Horse Vineyards and Kistler ...
5/5Exceptional! (15 reviews)
Amazing Family Getaway
"This property was absolutely beautiful from the grand gated entrance to the surrounding countryside. We actually rented both the main house and nearby guesthouse which is located just a short distance away. Both of these were well maintained and lovely. We had a few occasions where we needed to contact ..."

Reviewed on 10 Jul 2021

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The Dalya Estate- features 2 renovated homes, located on a small vineyard estate
Secluded Sonoma Country Retreat Views Pool-Spa-Vineyard-Olive Grove
This family-friendly Sonoma holiday home is located in the mountains, within 3 mi (5 km) of Sonoma TrainTown Railroad and Sonoma State Historic Park. Depot Park ...
4.9/5Exceptional! (47 reviews)
Perfect Sonoma Escape
"This home is the perfect retreat for those looking to have a true Sonoma experience! Complete with a big family table outside (a la Parenthood), two master bedrooms, a olive grove, a vineyard and a delicious pool… our group of women had the best time!"

Reviewed on 24 Aug 2021

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Secluded Sonoma Country Retreat Views Pool-Spa-Vineyard-Olive Grove
Devita Bungalow - A Great Place to Relax and Unwind  (license # VR09-0016)
This family-friendly Napa holiday home is within 1 mi (2 km) of Napa Premium Outlets and Uptown Theater. Napa Valley Wine Train and Downtown Napa Association ...
4.8/5Exceptional! (58 reviews)
Nice Napa Bungalow
"Cute little bungalow in nice residential neighborhood. Backyard is the best! One minor snafu at check in but owner was very quick to respond and rectify. Would definitely stay again."

Reviewed on 27 Aug 2021

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Devita Bungalow - A Great Place to Relax and Unwind (license # VR09-0016)
Healdsburg Bliss House-Sonoma Wine Country Panoramic Views(Fully Remodeled 2021)
Located in the heart of Healdsburg, this holiday home is within 2 miles (3 km) of Healdsburg Plaza, Healdsburg Center for the Arts and Healdsburg Museum. Raven ...
4.8/5Exceptional! (95 reviews)
Great place to relax....
"The owners are very conscientious. The house is very comfortable. The view is fantastic, and if you like a private, quiet place to spend a few days off...it doesn't get much better."

Reviewed on 14 Sep 2021

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Healdsburg Bliss House-Sonoma Wine Country Panoramic Views(Fully Remodeled 2021)
Worldmark Windsor/Healdsburg Wine country resort Condos 3BEDROOM 2BATH Sleeps8
This family-friendly Windsor holiday home is within 2 mi (3 km) of Windsor Golf Club and Pacific Coast Air Museum. Russian River and Luther Burbank Center for ...
4.4/5Excellent! (11 reviews)
Clean, spacious apartment, nice pool area
"You need a car to get around, though the small downtown of Windsor is only a mile away. It had a nice farmers market and there are lots of wineries and tourist attractions nearby. Had a brief timeshare pitch while waiting to check in. The condo was clean and had space for a group of 5, the kids enjoyed ..."

Reviewed on 16 Jun 2021

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Worldmark Windsor/Healdsburg Wine country resort Condos 3BEDROOM 2BATH Sleeps8
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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.

Other property types in St. Helena

Auberge Du Soleil

Auberge Du Soleil

5 out of 5
180 Rutherford Hill Rd, St. Helena, CA
The price is £1,342 per night from 17 Oct to 17 Oct
4.8/5Exceptional! (60 reviews)
"This property is perfect for anyone that wants to feel like they are transported to Europe but only have a weekend to have a vacation. Take advantage of all the complimentary amenities when staying here. Ask for a canvas to paint on, and try painting on your balcony. Then at midnight go for a swim ..."

Reviewed on 11 Sep 2021

Auberge Du Soleil
Rancho Caymus Inn

Rancho Caymus Inn

3.5 out of 5
1140 Rutherford Rd., St. Helena, CA
The price is £369 per night from 21 Sep to 21 Sep
4.9/5Exceptional! (489 reviews)
"Amazing place! Very convenient location."

Reviewed on 15 Sep 2021

Rancho Caymus Inn
El Bonita Motel

El Bonita Motel

2 out of 5
195 Main Street, St. Helena, CA
The price is £134 per night from 22 Sep to 22 Sep
4.4/5Wonderful! (584 reviews)
"Great location to winery’s"

Reviewed on 19 Sep 2021

El Bonita Motel
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.

St. Helena Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in St. Helena?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in St. Helena?

Choose from 429 beautiful holiday homes in St. Helena for your getaway.


How much is a holiday home in St. Helena?

You can find perfect holiday homes in St. Helena for as low as £134 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in St. Helena?

Find the best deals on St. Helena holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in St. Helena?

There’s no better way to spend your well-earned holiday than in a private, cosy St. Helena holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore St. Helena.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your St. Helena holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in St. Helena—and book all your travel in one place. Save even more when you bundle your bookings together. Add a St. Helena car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

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