St. Helena Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in St. Helena

Our top choices for St. Helena vacation rentals

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (240)
"We had a great stay! Thank you.Pictures don't do justice, this place is superb!"
The price is ￥257,303
￥332,509 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
Exterior

Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019

9.8 out of 10, Exceptional, (90)
"House was great- spacious and beautiful backyard with pool. Easy to find and access with lots of parking, plus walking distance to restaurants and shopping! Would absolutely recommend to a group or family. "
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
RiverPointe Napa Valley Resort
Exterior

RiverPointe Napa Valley Resort

3.0 star property
8.8 out of 10, Excellent, (1305)
"The trail nearby along the river was nice. "
The price is ￥16,011
￥22,640 total
includes taxes & fees
Sep 1 - Sep 2
RiverPointe Napa Valley Resort
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Outdoor pool, a heated pool

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

9.8 out of 10, Exceptional, (89)
"The house was phenomenal and we truly enjoyed our stay. The bedrooms all have large beds and bathrooms and are separate which provided nice privacy. The hot tub, common areas, and view were all amazing."
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Historic Cuneo Cottage Downtown Sonoma
Outdoor dining

Historic Cuneo Cottage Downtown Sonoma

9.4 out of 10, Exceptional, (85)
"We enjoyed staying in your Cuneo Cottage. Loved the history and pictures throughout the house and the proximity to the Plaza, hiking trail and Sebastiani Winery!! "
The price is ￥68,411
￥122,042 total
includes taxes & fees
Sep 6 - Sep 7
Historic Cuneo Cottage Downtown Sonoma
Casa Bella Estate in Wine Country w/ New Pool!
Outdoor dining

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (130)
"Great place to celebrate family members birthdays and Mother’s Day. Excellent location in Sonoma County close to wineries and easy access to SFO and Santa Rosa Airports. Walking distance to a great coffee shop and two wine tasting rooms. Nice large fenced area with pool, jacuzzi, outdoor grill and gathering area. We also enjoyed the covered front porch for relaxing and enjoying the outdoors."
The price is ￥386,023
￥621,500 total
includes taxes & fees
Sep 20 - Sep 21
Casa Bella Estate in Wine Country w/ New Pool!
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Fridge, microwave, oven, stovetop

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (65)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (49)
"Cute garden area, quiet, nice all inclusive spot"
The price is ￥28,524
￥31,804 total
includes taxes & fees
Sep 2 - Sep 3
Backyard Garden Oasis
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA
Outdoor pool

Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

9.8 out of 10, Exceptional, (106)
"Great stay from start to finish. We booked this for a trip with friends to celebrate my husband's 50th birthday. Communication with Tom was great. Was able to checkin a little early and allowed us to have ballons delivered before our arrival for a surpise for my husband. Plenty of space for 11 adults. Overall a great time."
The price is ￥132,180
￥222,586 total
includes taxes & fees
Sep 25 - Sep 26
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Smart TV, DVD player, books, stereo

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

9.8 out of 10, Exceptional, (190)
"Comfortable and easy flow of kitchen, living and dining areas. Close to wineries and Sonoma Square."
The price is ￥62,465
￥128,280 total
includes taxes & fees
Sep 22 - Sep 23
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (63)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate
Fridge, microwave, oven, stovetop

Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

10.0 out of 10, Exceptional, (9)
"The property was great for a decent sized group! Nicely located and provided excellent space and amenities."
The price is ￥138,185
￥239,783 total
includes taxes & fees
Sep 4 - Sep 5
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate
When in Glen | Sonoma | Panoramic Views | 3bed / 3bath
Pool

When in Glen | Sonoma | Panoramic Views | 3bed / 3bath

10.0 out of 10, Exceptional, (10)
"Beautiful homeSpacious Well appointedVery comfortable beds"
The price is ￥56,607
￥122,506 total
includes taxes & fees
Sep 3 - Sep 4
When in Glen | Sonoma | Panoramic Views | 3bed / 3bath
Charm and Modern Luxury in Heart of Wine Country
Fridge, microwave, oven, stovetop

Charm and Modern Luxury in Heart of Wine Country

10.0 out of 10, Exceptional, (138)
"We had a great time, place was definitely roomy for the four of us. Great kitchen to cook in."
Charm and Modern Luxury in Heart of Wine Country
Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home
Property grounds

Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home

10.0 out of 10, Exceptional, (289)
"Host gave great recommendations and was always hellful. Location great with easy access to restaurants and short drive to wineries "
The price is ￥51,313
￥83,219 total
includes taxes & fees
Sep 29 - Sep 30
Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
Property grounds

Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

9.8 out of 10, Exceptional, (202)
"Stunning home on a beautiful property. "
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (22)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is ￥43,962
￥59,862 total
includes taxes & fees
Sep 3 - Sep 4
Escape to Wine County in your independant Cottage in Downtown Calistoga
Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!
Interior

Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!

10.0 out of 10, Exceptional, (82)
"Had a great time!"
Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!
Downtown Napa Cottage- walking distance to City Center
Exterior

Downtown Napa Cottage- walking distance to City Center

9.8 out of 10, Exceptional, (129)
"Amazing downtown Napa cottage, host was responsive and thoughtful!"
The price is ￥50,234
￥82,633 total
includes taxes & fees
Sep 1 - Sep 2
Downtown Napa Cottage- walking distance to City Center
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (234)
"The property was stunning and made for the perfect stay! William was a wonderful host and was super quick to respond to my questions. Would highly recommend! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
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

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!

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Frequently asked questions

Can I find vacation rentals in St. Helena?

Yes, we give you a choice of vacation rentals close to top sights in St. Helena, or you can select a more remote option if you're looking for relaxation. Our travelers say St. Helena has a good selection of top-notch restaurants and wineries. Leave some time to check out the shops and spas during your trip.

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

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This highly rated vacation home rental in St. Helena is located in the city center and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in St. Helena?

Expedia has 65 vacation 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 vacation rentals like in St. Helena?

Vacation rentals are private properties you can reserve for a couple days or more in St. Helena. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family getaway.