St. Helena Vacation Homes

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Our top choices for St. Helena holiday homes

1. Cottage House: Private 3-Bedroom Home in Downtown St. Helena!

Downtown St. Helena

Kim B.

HK$14,853 total

includes taxes & fees

12 Nov - 13 Nov

A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

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

Downtown St. Helena

Juri A.

HK$17,235 total

includes taxes & fees

5 Nov - 6 Nov

Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

3. Ambrose Bierce House: Private 5-Bedroom Downtown St. Helena Historic Home

Downtown St. Helena

Steve H.

HK$17,902 total

includes taxes & fees

19 Nov - 20 Nov

A spacious living area with a fireplace, a large bookshelf, and a view of the outdoors.

4. RustRidge House, two bedroom two bath home

St Helena

Kristen F.

HK$7,464 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a fireplace, built-in shelves, and a large window overlooking a deck.

5. Sonoma Creek Haven - Creekside Hot Tub Retreat

Kenwood

Kathryn J.

HK$6,466 total

includes taxes & fees

29 Nov - 30 Nov

A wooden deck with potted plants, a bench, and a building with large windows and a door.

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

Glen Ellen

Robert K.

HK$4,280 total

includes taxes & fees

19 Nov - 20 Nov

A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

7. Glen Ellen Retreats Coastal Cottage

Glen Ellen

Amanda D.

HK$4,381 total

includes taxes & fees

11 Nov - 12 Nov

A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

8. Glen Ellen Retreats Sunset Cottage

Glen Ellen

patrick s.

HK$4,412 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

9. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Santa Rosa

Abigail M.

HK$3,600 total

includes taxes & fees

4 Nov - 5 Nov

A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

HK$2,102 total

includes taxes & fees

16 Nov - 17 Nov

A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

11. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen

Amy

HK$4,694 total

includes taxes & fees

9 Nov - 10 Nov

A pool with a wooden deck and lounge chairs, surrounded by lush greenery and a mountainous backdrop.

12. Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more

Glen Ellen

Garrett B.

HK$7,985 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

13. Cloud 9 - A Retreat for Bliss and Happiness

Glen Ellen

Amy M.

HK$11,359 total

includes taxes & fees

12 Nov - 13 Nov

A two-story house with a garage, a balcony, and a driveway.

14. King bedroom #1 Wine Country Gateway With BBQ+Billiards

Sonoma

HK$2,040 total

includes taxes & fees

4 Nov - 5 Nov

15. Silverado Napa Luxury 1 Bed Jr. Suite

Napa

Shayna

HK$1,656 total

includes taxes & fees

17 Nov - 18 Nov

A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

16. Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

Adam C.

HK$2,667 total

includes taxes & fees

6 Nov - 7 Nov

A spacious living area with a high ceiling, large windows, a fireplace, and a balcony with a view of the hills.

17. Modern Farmhouse Villa with Captivating Panoramic Views, Hot Tub and Sauna!

Santa Rosa

James H.

HK$6,979 total

includes taxes & fees

23 Nov - 24 Nov

Lounge poolside under umbrellas with wine, games, and playful floats for a sun soaked afternoon with friends.

18. Base Camp

Kenwood

HK$28,512 total

includes taxes & fees

10 Nov - 11 Nov

A dining area with a long wooden table set for six, surrounded by wooden chairs with blue patterned cushions.

19. Charming Wine Country Inn, Whole House Rental w/Private Suites, Walk to Wineries

Calistoga

Lauren H.

HK$10,213 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor patio area with stone flooring, wooden furniture, and string lights.

20. Casa Bella Estate in Wine Country w/ New Pool!

Kenwood

Maitrayee s.

HK$32,934 total

includes taxes & fees

28 Nov - 29 Nov

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Top St. Helena Hotel Reviews

Harvest Inn

10/10 Excellent

"Such a beautiful and relaxing stay."

Fairmont Sonoma Mission Inn & Spa

8/10 Good

"It was a beautiful old restored property. Loved the big jacuzzi tub in the Mission Spa suite. I felt we should have been able to do the geothermal pools for free due to paying $800/night for the room. We didn't have a four poster bed as advertised in all the photos and the room seemed smaller. Spa pools closed at 8pm which was much too early for us. No free breakfast, was just a lot more money for less amenities than we experienced in our hotel the prior night which cost 60% as much. Could be a more memorable experience ti make it more personalized. I called ahead letting the hotel know we were celebrating a double birthday and they did put some flowers and chocolate in the room which was nice, and the man at the spa was very nice to us and gave us a discount due to the fact that we only had 30 mins to go in the spa pools and the valet parking guys as well let us park for free overnight. I'd say the staff on site were very friendly and helpful but the sales team reps and the people I spoke to over the phone/the corporate Fairmont system and pricing for this hotel made it overpriced for the value we received. We still enjoyed ourselves but it could have been better."

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