St. Helena vacation rentals

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Top-rated vacation rentals in St. Helena

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Calistoga

4.9 out of 5 average rating, 413 reviews

Luxury Cottage in Downtown Calistoga, Napa Valley

Each of our 16 Independent private cottages is uniquely appointed with there own air-circulation system, semi-private porch, reclaimed hardwood floors, vaulted ceilings with skylights, soft linens and plush down bedding on a luxurious king bed. Sink into overstuffed chairs by your own roaring fire or restore in a deep-soaking for two and separate shower. Rooms are set up studio style with separate bathroom area that closes. Want to stay connected? Enjoy the flat screen TV and complimentary High speed Wifi access. Our cottages are designed for double occupancy, but we can accommodate a third guest by adding an extra bed, with advance notice. We have one Cottage that we can split into two twins. Please call us directly to find out the availability of the Twin Cottage. We allow dogs that less than 40 pounds in designated cottages for an additional nightly fee of $50/dog.

Nov 13 – 20

G$92,107 GYD per night

Guest favorite

Apartment in Napa

4.96 out of 5 average rating, 774 reviews

Carriage House at Main Street Farmhouse!

Clean, comfortable, space on this Farmhouse property dating back to 1880. Enter exact number of guests for correct pricing $60 per person after 2. Studio apartment with queen bed, full bathroom, kitchenette with microwave, electric sautée pan, toaster, coffee and tea, (no full oven or stove) dinette, tv area and sofa/sleeper. Beautiful patio with fire pit. Not suitable for children under the age of 12. Community fee (local lodging tax of 15%) is added to reservation when confirmed by guest.

Feb 27 – Mar 6

G$58,780 GYD per night

Guest favorite

Apartment in Napa

5.0 out of 5 average rating, 316 reviews

Mendez on Main #2 / King Bed/1 bath Walk to town

Indulge in Napa's finest restaurants, wine tasting, and nightlife from our beautifully restored and remodeled apartment in our Victorian home, just a 10-minute stroll from downtown. Our apartment is fully equipped with all the amenities you'd expect, (*No stove) creating a comfortable space for your stay. For the peace and relaxation of all guests, please note that we do not allow pets or children under 12. You can book with confidence knowing that we have a Use Permit from the City of Napa.

Jan 31 – Feb 7

G$68,697 GYD per night

Guest favorite

Home in Napa

4.99 out of 5 average rating, 232 reviews

A Peaceful home in the heart of Napa Valley

A peaceful home in the heart of Napa Valley - the Arbor House is less than one mile from Downtown Napa but far enough away from the hustle and bustle of downtown. This charming historical home has four bedrooms, each with ensuite bathroom. Enjoy the living room, dining room and California native garden featuring a gazebo, botanical walkways and spacious sunlit decks. We are legally permitted to rent to Napa Valley visitors. Ask about our other Napa listings if the dates here are booked.

Dec 10 – 17

G$214,744 GYD per night

Guest favorite

Home in Calistoga

4.95 out of 5 average rating, 172 reviews

Cedar Street Victorian

Turn of the century Victorian heritage home less than half a block walking distance to restaurants, wine tasting, shopping, spas and the year round Sat farmers market. You’ll love the house because of the comfy beds, the outdoor space, and the neighborhood. It is good for couples, solo adventurers, business travelers, and adult family functions. Pioneer park is right across the street. Every Thurs night in the summer months there are free concerts you can enjoy from the front porch.

Sep 20 – 27

G$140,085 GYD per night

Guest favorite

Condo in Napa

4.98 out of 5 average rating, 124 reviews

Chic Retreat at Silverado: Pool Access, Kitchen

Imagine vacationing a stone’s throw from Napa Valley wineries while staying in a resort so entertaining that the fun and relaxation is multiplied exponentially. You’ll have every comfort and convenience in this stylish condo with king bed, 2 patios and access to resort amenities, such as restaurants, pool, Tesla charging station, and laundry. Guests rave about cleanliness, décor, and responsive host. Make this condo your headquarters for wine tasting or exploring downtown Napa/Yountville

Oct 8 – 15

G$96,776 GYD per night

Guest favorite

Villa in Napa

4.96 out of 5 average rating, 101 reviews

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Mar 25 – Apr 1

G$184,519 GYD per night

Guest favorite

Cabin in Calistoga

4.87 out of 5 average rating, 256 reviews

Wine Country Mountain Home - Spring discounts

Spring 2024 discounts. Whole house luxury for 2 in a Private forested location. Starlink WiFi, Forest at your front door. Clean and Comfortable vintage cabin In the mountains. Mid way between Napa and Sonoma valleys: 7 miles to Calistoga; 10 miles to Santa Rosa. NO cleaning fee at check out. Self-check-in with lock box. Professionally cleaned and sanitized before all check ins. Monthly discounts of 60%, weekly discounts 25% for travelers looking to work from home. Inquire with host.

Feb 12 – 19

G$39,333 GYD per night

Superhost

Condo in Napa

4.82 out of 5 average rating, 125 reviews

Studio Suite at Napa Resort with Wine Tasting Cave

Many of the area's most awarded wineries are just a short drive away. Only 10 minutes from downtown, home to Oxbow Public Market and the Napa Valley Wine Train, shopping & world-class dining. Covid-19: Enhanced cleaning protocols in place. • Guest checking in must be 21+ with valid ID & card for $250/night refundable security deposit (credit card only) • Resort fee of $6.32+tax/night and cleaning fee paid at check-in • Name on reservation must match photo ID at check-in

Apr 27 – May 2

G$26,263 GYD per night

Guest favorite

Guest suite in Napa

4.96 out of 5 average rating, 343 reviews

Perfect Location w/ Charm

Permitted by the city of Napa: #VR16-0008 Our guest suite with private entrance in our charming Napa cottage style home provides you with a comfortable home away from home. Your room and bathroom is completely private and there are no shared spaces in the house. The backyard is shared with us. It's bright and sunny, and you are perfectly located for walking downtown or exploring the valley.

Jul 7 – 14

G$37,630 GYD per night

Guest favorite

Guest suite in Saint Helena

4.92 out of 5 average rating, 294 reviews

One Bedroom Wine Country Getaway

Light-filled one beroom lower apartment in the historic west side of St. Helena walking distance to downtown shops, dining and wineries! A short walk 7 minute walk to downtown St. Helena, restaurants and wineries. Owners live in the upstairs unit and are out-of-sight but more than happy to help with local tips and recommendations! St Helena STR Permit: PL19-035

Jun 27 – Jul 4

G$70,640 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 675 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax.

Oct 27 – Nov 3

G$22,772 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for St. Helena vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near St. Helena's top sights

Farmstead at Long Meadow Ranch79 locals recommend

The Culinary Institute of America at Greystone36 locals recommend

Meadowood Napa Valley12 locals recommend

Pizzeria Tra Vigne24 locals recommend

Goose and Gander47 locals recommend

The Charter Oak Restaurant21 locals recommend

Other great vacation rentals in St. Helena

Guest favorite

Guesthouse in Glen Ellen

4.91 out of 5 average rating, 930 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Oct 28 – Nov 4

G$28,416 GYD per night

Guest favorite

Bungalow in Napa

4.87 out of 5 average rating, 686 reviews

Hot Tub | 2 Bedroom | 2 Bath | Dwntown Napa Escape

Jan 26 – Feb 2

G$124,840 GYD per night

Guest favorite

Guesthouse in Sonoma

4.93 out of 5 average rating, 137 reviews

Cozy Sonoma Studio Nearby Wineries and Restaurants

Dec 18 – 25

G$33,533 GYD per night

Guest favorite

Home in Napa

4.93 out of 5 average rating, 161 reviews

Casa Alta with Hot Tub near Oxbow Market!

Jan 2 – 9

G$110,798 GYD per night

Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 762 reviews

Private Getaway in West Santa Rosa

Jan 13 – 20

G$20,571 GYD per night

Guest favorite

Home in Napa

4.88 out of 5 average rating, 320 reviews

Downtown Napa Retreat-Walking Distance to Main St.

Dec 12 – 19

G$51,852 GYD per night

Guest favorite

Guesthouse in Glen Ellen

4.92 out of 5 average rating, 486 reviews

Glen Ellen Hideaway

Oct 4 – 11

G$33,003 GYD per night

Guest favorite

Apartment in Penngrove

4.97 out of 5 average rating, 382 reviews

Valley View-Sonoma Mountain Terrace

Jun 16 – 23

G$36,514 GYD per night

Show all

Other great vacation rentals in St. Helena

Guest favorite

Home in St. Helena

5.0 out of 5 average rating, 11 reviews

Charming Wine Country cottage close to downtown

Jul 2 – 9

G$101,817 GYD per night

Guest favorite

Cottage in Calistoga

5.0 out of 5 average rating, 31 reviews

Charming Vineyard Cottage

Feb 13 – 20

G$166,510 GYD per night

Guest favorite

Home in Calistoga

4.9 out of 5 average rating, 29 reviews

Calistoga Tejas Trails

Oct 22 – 29

G$109,122 GYD per night

Guest favorite

Home in Calistoga

5.0 out of 5 average rating, 17 reviews

Wine Country Retreat with Vineyard Views

Aug 22 – 29

G$113,275 GYD per night

Superhost

Guesthouse in Calistoga

4.94 out of 5 average rating, 35 reviews

'Modsita'

Jan 27 – Feb 3

G$194,347 GYD per night

Guest favorite

Home in Calistoga

4.96 out of 5 average rating, 68 reviews

Charming Home Just Steps From Wine & Hot Springs!

Sep 7 – 14

G$126,500 GYD per night

Guest favorite

Home in Calistoga

4.96 out of 5 average rating, 24 reviews

Calistoga Calm with Napa Valley views

Nov 19 – 26

G$100,205 GYD per night

Superhost

Farm stay in St. Helena

4.79 out of 5 average rating, 125 reviews

Private winery farm stay in St Helena, Ca.

Feb 17 – 24

G$47,249 GYD per night

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Quick stats about vacation rentals in St. Helena

Total rentals
300 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
1.6K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in St. Helena?
Yes! Work meets play with ease at over 20 vacation rentals in St. Helena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in St. Helena?
Four-legged friends are welcome in St. Helena. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there St. Helena vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in St. Helena, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in St. Helena have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in St. Helena. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in St. Helena?
St. Helena has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in St. Helena have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in St. Helena. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in St. Helena have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in St. Helena. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in St. Helena?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 70 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

St. Helena vacation rentals

Top-rated vacation rentals in St. Helena

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for St. Helena vacation rentals

Stay near St. Helena's top sights

Other great vacation rentals in St. Helena

Guesthouse in Glen Ellen

Bungalow in Napa

Guesthouse in Sonoma

Home in Napa

Apartment in Santa Rosa

Home in Napa

Guesthouse in Glen Ellen

Apartment in Penngrove

Other great vacation rentals in St. Helena

Home in St. Helena

Cottage in Calistoga

Home in Calistoga

Home in Calistoga

Guesthouse in Calistoga

Home in Calistoga

Home in Calistoga

Farm stay in St. Helena

Quick stats about vacation rentals in St. Helena

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in St. Helena?

Are there pet-friendly vacation rentals in St. Helena?

Are there St. Helena vacation rentals on Airbnb with pools?

Do apartment rentals in St. Helena have wifi?

Are there family-friendly vacation rentals in St. Helena?

Do house rentals in St. Helena have self check-in?

Do house rentals in St. Helena have a bbq area?

What are the most popular amenities for House Rentals in St. Helena?

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