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Compare 820 Vacation Homes in St. Helena with updated reviews, rates, and availability.

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Bliss House Panorama View 1
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
10.0 out of 10, Exceptional, (228)
"We had an amazing stay at this house! The location was ideal—close to everything in town, making it so convenient to explore. The house itself was spotless, beautifully maintained and stocked with everything you could possibly need. It felt like a true home away from home. The property manager was incredibly responsive and thorough, making the entire experience seamless and stress-free. We couldn’t recommend this place more—it’s perfect for anyone looking for a comfortable, well-equipped and...
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Family / Kitchen
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (219)
"The house was great and the location is super! The sound system in the house was a little challenging for us "old folks", but we made it work!! Would go back again for sure!"
The price is AED 6,060
AED 7,743 total
includes taxes & fees
22 Nov - 23 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
Living area
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
9.8 out of 10, Exceptional, (168)
"We loved this property. Lots of space to spread out as well as great communal areas for visiting. Beautiful view of a quiet golf course with a lovely patio. Owner was very helpful and responsive to questions. Location great to all the wineries we wanted to visit. We didn’t use the pool but it provided a nice view from the living room. 4th bedroom was kindof small, good for kids. The house was a little dated, but well kept up. Overall, loved our stay here!"
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
KampCasa Rustic-Lux Sonoma-County Wine Country Unique Private Home Property
Outdoor dining
KampCasa Rustic-Lux Sonoma-County Wine Country Unique Private Home Property
2.0 star property
8.8 out of 10, Excellent, (6)
"KampCasa was really fun. The set up of the property with all the seating lounge and play areas is so awesome! We loved the room with the pool table and the record player, the trampoline, the swings, the hammocks, the big bathtubs and the hot tub. A few things to be aware of - it is a rustic experience. While beautiful there were several things on the property that seemed unfinished or in progress. The host said a pig party had just left before us that had done some damage - so hopefully all...
The price is AED 1,087
AED 2,995 total
includes taxes & fees
22 Nov - 23 Nov
KampCasa Rustic-Lux Sonoma-County Wine Country Unique Private Home Property
The Corner Cottage ~ Downtown out your door with Private Vineyard
'An old home with a new soul.'
The Corner Cottage ~ Downtown out your door with Private Vineyard
10.0 out of 10, Exceptional, (209)
"Such a convenient location, plenty of space, & a great host!"
The Corner Cottage ~ Downtown out your door with Private Vineyard
New Modern House in Sonoma Valley's Best Area
Main Living Room
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (232)
"Such a great location to wind down after a day exploring wine country! Secluded, peaceful, and accommodating. With all of the glass, it felt like you we immersed in nature while being cradled in creature comforts. "
New Modern House in Sonoma Valley's Best Area
Beautiful 3,000 SF Castle in the Vineyards
WELCOME TO THE CASTLE IN THE VINEYARDS
Beautiful 3,000 SF Castle in the Vineyards
9.8 out of 10, Exceptional, (200)
"What a wonderful place to get away. Michael, the host was so friendly and told us the history of the castle. This was a four day getaway with friends and we would love to go back as soon as possible. The home was warm and cozy very unique. The amenities were perfect. first class beddings something you would expect in a five star hotel. Great kitchen with everything you can possibly need to prepare a meal.. We can’t wait to go back!"
Beautiful 3,000 SF Castle in the Vineyards
1 Block To St. Helena Main Street Shops-Restaurants! Avail Dec 2-5, 8-12 Jan 2-5
Private kitchen
1 Block To St. Helena Main Street Shops-Restaurants! Avail Dec 2-5, 8-12 Jan 2-5
10.0 out of 10, Exceptional, (242)
"Close to restaurants & property is lovely. Beautiful backyard!"
1 Block To St. Helena Main Street Shops-Restaurants! Avail Dec 2-5, 8-12 Jan 2-5
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Enjoy lawns, gardens, and a walk in through our vineyards
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, (230)
"Just like the pictures. Grounds were gorgeous & the stay was very relaxing. My family had a wonderful time. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Pool Paradise in Wine Country!
Pool
Pool Paradise in Wine Country!
3.0 star property
10.0 out of 10, Exceptional, (4)
"The property was well appointed with everything we could need for our stay and the hot tub was great, as was the game room. Beds were comfy and the couches and blankets fit all 7 of us. Small blemishes here and there was well as some general maintenance needed on the deck / interior, but nothing out of the ordinary for a house like this. Overall very enjoyable stay for the entire extended family."
Pool Paradise in Wine Country!
Beautiful Home in Northwest Napa
Exterior
Beautiful Home in Northwest Napa
10.0 out of 10, Exceptional, (21)
"Excellent house in safe neighborhood, near major roads to explore the Napa/Sonoma region."
Beautiful Home in Northwest Napa
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Maison Jacqueline in summer..
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (181)
"We had the best time at this cute rental property. It was comfortable, cute and felt private. This place is perfect for a group and is equipped with anything you might need. We cooked in the kitchen one evening and were in a good spot to tour Healdsburg one day and wineries in Sonoma the next. Would stay again and recommend to friends and family. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Elegance & Charm 2 blocks to Sonoma Square, from 249 off season
Kitchen
Elegance & Charm 2 blocks to Sonoma Square, from 249 off season
9.8 out of 10, Exceptional, (192)
"Everything from first communication to condition of the rental was great. Restaurant recommendations were appreciated; if you stay here don’t miss Salumeria Ovello 2 doors down. It’s amazing! Not having to drive into the square is worth it in spades. Can’t miss with this rental just be aware that light switches are not intuitive 😉"
Elegance & Charm 2 blocks to Sonoma Square, from 249 off season
Elegant Penthouse 2 blocks from Sonoma Plaza.
Interior
Elegant Penthouse 2 blocks from Sonoma Plaza.
9.8 out of 10, Exceptional, (198)
"Really enjoyed the apartment, was spacious and charming. Very walkable to downtown Sonoma restaurants and tasting rooms. Nice kitchen and bathroom. Very good rental!"
Elegant Penthouse 2 blocks from Sonoma Plaza.
Auberge Sonoma *South Suite* - Includes Wine Tasting Passport
Exterior
Auberge Sonoma *South Suite* - Includes Wine Tasting Passport
10.0 out of 10, Exceptional, (129)
"This property was fabulous for us we could not have asked for a better property.Thank you"
Auberge Sonoma *South Suite* - Includes Wine Tasting Passport
Sonoma Wine Country Madison Escape TOT #2380N
Sonoma Wine Country Madison Escape TOT #2380N
9.6 out of 10, Exceptional, (103)
"Clean and large home. "
Sonoma Wine Country Madison Escape TOT #2380N
The Sonoma Valley Cottage
The Sonoma Valley Cottage
9.6 out of 10, Exceptional, (5)
"Cool place. Place as easy to use. Lots of space inside"
The Sonoma Valley Cottage
Calistoga Dream Inn
Exterior
Calistoga Dream Inn
10.0 out of 10, Exceptional, (9)
"This house was perfect. It was beautifully decorated and extremely clean. The location couldn't have been better. It's right in the heart of Calistoga, walkable to so many things. I would definitely stay here again. "
Calistoga Dream Inn
Great Value - Heart of the Wine Country - Pool-Hot Tub 3K 1Q Bedroom
Pool Area - hot tub above water fall
Great Value - Heart of the Wine Country - Pool-Hot Tub 3K 1Q Bedroom
9.6 out of 10, Exceptional, (108)
"We had a fantastic time in Sonoma. The house was perfect for our group. It has everything we we needed we needed "
Great Value - Heart of the Wine Country - Pool-Hot Tub 3K 1Q Bedroom
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Indoor dining table
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (211)
"We enjoyed our stay at the home. The panoramic windows in the living area provided wonderful views of the valley and wildlife. It was very well stocked and restful!"
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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Other property types in St. Helena

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
View from Vineyard
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (222)
"We wanted to introduce friends from East Coast to the Napa Valley- history to modern day. This rare restored farmhouse with views of vineyards was ideal. Authentic, comfortable (with just the right amount of modern amenities but not too much to destroy the charm), spacious, wonderfully furnished, with superb kitchen (fully stocked), and screened porches, etc. The hosts were easy to communicate with and would stay again in a heartbeat. We have stayed at 60+ rentals around the world... this unique...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Family / Kitchen
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (219)
"The house was great and the location is super! The sound system in the house was a little challenging for us "old folks", but we made it work!! Would go back again for sure!"
The price is AED 6,060
AED 7,743 total
includes taxes & fees
22 Nov - 23 Nov
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
Pool
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
9.8 out of 10, Exceptional, (85)
"The home was located in a beautiful area. Lots of great shops and restaurants within walking distance."
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
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.