St. Helena Holiday Homes from £209: Search Holiday Homes in St. Helena

A rustic stone building with a red door and a wooden balcony, surrounded by lush greenery and a vintage wooden cart.

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for St. Helena holiday homes

1. Downtown Cottage House

Downtown St. Helena

Kim B.

includes taxes & fees

12 Oct - 13 Oct

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

"Beautiful rustic property. Great for family gatherings with large kitchen and open layout. It’s very close to St. Helena downtown where you could walk ~10 mins and even right across the street from Beringer. The Host was very responsive when we were checking in and helped us resolve our user-error quickly. Our family enjoyed our brief time here, and we would consider coming back for another reunion in the future."

David

includes taxes & fees

4 Oct - 5 Oct

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

Downtown St. Helena

Steve H.

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.

includes taxes & fees

2 Oct - 3 Oct

A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

5. Modern Organic 3BR Oasis w/ Creek&Near State Park

Kenwood

Linda Z.

includes taxes & fees

5 Oct - 6 Oct

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

6. Glen Ellen Retreats Coastal Cottage

Glen Ellen

Amanda D.

includes taxes & fees

1 Oct - 2 Oct

A living room with a red sofa, a green armchair, and a red armchair with patterned cushions. There is a coffee table with books and a lamp. The room has wooden flooring and a large window with blinds.

7. Napa Valley Retreat in Calistoga!

Calistoga

linda k.

includes taxes & fees

4 Oct - 5 Oct

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

8. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

includes taxes & fees

4 Oct - 5 Oct

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

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

Sonoma

includes taxes & fees

1 Oct - 2 Oct

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

10. Glen Ellen Retreats Sunset Cottage

Glen Ellen

Michelle W.

includes taxes & fees

7 Oct - 8 Oct

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

ladonna A.

includes taxes & fees

6 Oct - 7 Oct

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

12. Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

Adam C.

includes taxes & fees

1 Oct - 2 Oct

13. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

includes taxes & fees

13 Oct - 14 Oct

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

14. Wine Country Cottage Escape

Fulton

Tina A.

includes taxes & fees

7 Oct - 8 Oct

A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

15. Charming Wine Country Home w/Hot Tub near Downtown

Santa Rosa

Joel B.

includes taxes & fees

1 Oct - 2 Oct

A spacious kitchen with a large island, a dining area with a sofa and chairs, and a view of the outdoors.

16. Silverado Napa Breath Taking Remodel 3 bed 2 bath

Napa

Tracie T.

includes taxes & fees

6 Oct - 7 Oct

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

17. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Healdsburg

Riley F.

includes taxes & fees

1 Oct - 2 Oct

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

18. Wine Country Farmhouse with Hot Tub

Santa Rosa

Abigail M.

includes taxes & fees

4 Oct - 5 Oct

A terrace with wicker chairs overlooking a scenic valley.

19. The Moonlit Retreat + Casita,Bocce & Sunset Views!

Glen Ellen

"My family met for a family wedding and we stayed at this wonderful property . It is a perfect distance to get away yet close enough for ease of conveyance to stores , restaurants etc . The hosts were very good communicators and made us feel totally comfortable . The place was spotlessly clean and very comfortable . Nature abounds with deer , big bunnies and birds galore . Great guest experience and we would definitely stay again when visiting the area."

Alfie H.

includes taxes & fees

11 Oct - 12 Oct

A spacious living area with a leather sofa, wooden coffee table, and a dining table with chairs. There are plants, bookshelves, and a kitchen in the background.

20. Craftsman 2 blocks from Russian River Brewery!

Santa Rosa

Thomas L.

includes taxes & fees

1 Oct - 2 Oct

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top St. Helena Hotel Reviews

Silverado Resort

10/10 Excellent

"When checking in leave your luggage in the car because the rooms are outside far from the parking lot. But overall, it was very nice and clean. The pool was a little far but enjoyed it once I got there."

Archer Hotel Napa

10/10 Excellent

"Love this hotel! My husband and I stayed here for our anniversary and had such a wonderful experience. When we arrived, champagne and chocolate-covered strawberries were waiting for us in our room. We also enjoyed a couples massage at the spa and spent time relaxing at the rooftop. The second night, we came back to find confetti and a sweet “Happy Anniversary” note from housekeeping. It was little touches like this that made our stay feel extra special. The location is perfect—right in the middle of all the restaurants and bars and within walking distance of the river. The staff was incredibly friendly and welcoming. We had such a great experience and would definitely stay here again. Highly recommend!"

Find out more about St. Helena

St. Helena Holiday Homes information

Number of reviews	648
Accommodation	977 Holiday Homes
Lowest Price	£209
Highest Price	£1,728

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in St. Helena on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Helena holiday homes

1. Downtown Cottage House

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

3. Ambrose Bierce House

4. RustRidge House, two bedroom two bath home

5. Modern Organic 3BR Oasis w/ Creek&Near State Park

6. Glen Ellen Retreats Coastal Cottage

7. Napa Valley Retreat in Calistoga!

8. 2 Hidden Wine Country Gem Upstairs Unit

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

10. Glen Ellen Retreats Sunset Cottage

11. Glen Ellen Retreats Hot Tub Cottage

12. Cozy Wine Country Guesthouse with Private Pool & Yard

13. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

14. Wine Country Cottage Escape

15. Charming Wine Country Home w/Hot Tub near Downtown

16. Silverado Napa Breath Taking Remodel 3 bed 2 bath

17. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

18. Wine Country Farmhouse with Hot Tub

19. The Moonlit Retreat + Casita,Bocce & Sunset Views!

20. Craftsman 2 blocks from Russian River Brewery!

Find holiday rentals that suit your style

Top St. Helena Hotel Reviews

Silverado Resort

Elm House Inn

Oxford Suites Sonoma County

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Calistoga Motor Lodge and Spa

Napa Winery Inn

Archer Hotel Napa

Sheraton Sonoma Wine Country Petaluma

Find out more about St. Helena

St. Helena Holiday Homes information

Explore a world of travel with Expedia