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

Guesthouse in Glen Ellen

4.91 out of 5 average rating, 931 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Crow Cottage is newly rebuilt and decorated in an eclectic whimsical style by the artist owners. It is light and airy with a private shade deck and sunny patio. The Cottage has a queen bed. There is a portable A/C. The cottage is well insulated so it doesn't get too hot in the summer. There is also a fan. Set on a country lane just a 3 min walk to great restaurants & a gourmet market. While we do have rescued cats in our yard we don't let them in any of the rooms. If highly allergic, reconsider.

Oct 29 – Nov 5

G$28,361 GYD per night

Guest favorite

Apartment in Napa

4.96 out of 5 average rating, 776 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 9 – 16

G$58,665 GYD per night

Guest favorite

Apartment in Napa

5.0 out of 5 average rating, 317 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 6 – 13

G$68,564 GYD per night

Guest favorite

Condo in Napa

4.98 out of 5 average rating, 156 reviews

Elegant Napa Escape

A designer gem for your next vacation to the wine country! A warm and inviting Napa escape is situated on a lovely serene golf course. Has one bedroom /one bath, kitchen, dining area and living room. High ceilings add to the spacious open feel, along with large sliding glass doors from both the living room and bedroom, opening to a patio and picturesque views of the fairway. Beautifully furnished and handsomely appointed, all details for your comfort and relaxation have been attended to.

Jan 12 – 19

G$41,247 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 181 reviews

Wine Country Retreat

Nestled in an upscale leafy neighborhood with stunning views of Spring Lake Regional Park from the deck. This bright, air conditioned, space comes with its own deck and propane grill for your sole use. The cottage also has a kitchen with a refrigerator, range, dishwasher, microwave, toaster oven, Keurig coffee maker etc. We also have a washer and dryer in the property and a tv. The cottage has its own entrance and is attached to the main house. It's not a detached unit. TOT account #1847

Jan 25 – Feb 1

G$30,386 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 22 – 29

G$91,387 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.

Oct 9 – 16

G$139,812 GYD per night

Guest favorite

Villa in Napa

4.96 out of 5 average rating, 102 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 7 – 14

G$184,161 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.

Aug 7 – 14

G$39,256 GYD per night

Guest favorite

Apartment in Napa

4.95 out of 5 average rating, 350 reviews

A Private Guesthouse Studio – The Otter

the Otter studio - a peaceful standalone studio in the heart of Napa Valley wine country. the Otter studio is less than one mile from Downtown Napa but far enough away from the hustle and bustle to provide a tranquil retreat while retaining every thoughtful amenity. Enjoy our cozy living space. We are legally permitted to rent to Napa Valley visitors. Ask about our other Napa listings if the dates here are booked.

Dec 17 – 24

G$52,063 GYD per night

Guest favorite

Guest suite in Napa

4.97 out of 5 average rating, 344 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 14 – 19

G$36,877 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

Jul 13 – 20

G$106,598 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

Pizzeria Tra Vigne24 locals recommend

Goose and Gander47 locals recommend

Meadowood Napa Valley12 locals recommend

The Charter Oak Restaurant21 locals recommend

Other great vacation rentals in St. Helena

Guest favorite

Home in Calistoga

4.97 out of 5 average rating, 293 reviews

Intimate Farmhouse on Vineyard

Jun 7 – 14

G$90,424 GYD per night

Guest favorite

Home in Napa

4.88 out of 5 average rating, 321 reviews

Downtown Napa Retreat-Walking Distance to Main St.

Aug 6 – 13

G$70,802 GYD per night

Guest favorite

Home in Glen Ellen

5.0 out of 5 average rating, 126 reviews

Tuscan Wine Country Villa with Pool sleeps 6

Oct 31 – Nov 7

G$179,081 GYD per night

Guest favorite

Home in Sonoma

4.95 out of 5 average rating, 398 reviews

Zen House on 15 acres

Nov 29 – Dec 6

G$92,609 GYD per night

Guest favorite

Home in Glen Ellen

5.0 out of 5 average rating, 171 reviews

Walk Everywhere! Quiet Wine County Retreat! Views!

Jul 21 – 28

G$161,953 GYD per night

Guest favorite

Home in Napa

4.98 out of 5 average rating, 320 reviews

Vineyard House In The Heart Of Napa Valley

Dec 24 – 31

G$172,334 GYD per night

Guest favorite

Home in Napa

4.96 out of 5 average rating, 484 reviews

Come and Visit the Valley Sleeps 4 to 8 Guests

Jan 9 – 16

G$117,417 GYD per night

Guest favorite

Home in Napa

4.93 out of 5 average rating, 509 reviews

Kat's Place Napa Valley VR-16-0044

Aug 11 – 18

G$56,456 GYD per night

Show all

Other great vacation rentals in St. Helena

Guest favorite

Guesthouse in Glen Ellen

4.92 out of 5 average rating, 487 reviews

Glen Ellen Hideaway-TOT#2398

Jul 23 – 30

G$32,205 GYD per night

Guest favorite

Condo in Napa

4.99 out of 5 average rating, 152 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

May 30 – Jun 6

G$88,657 GYD per night

Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 763 reviews

Private Getaway in West Santa Rosa

Feb 1 – 8

G$20,531 GYD per night

Guest favorite

Guest suite in Glen Ellen

4.96 out of 5 average rating, 191 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Jun 11 – 18

G$31,118 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 250 reviews

Alexander Valley: Wine Lover and Cycling Paradise

Oct 2 – 9

G$39,308 GYD per night

Guest favorite

Guesthouse in Sonoma

4.93 out of 5 average rating, 138 reviews

Cozy Sonoma Studio Nearby Wineries and Restaurants

Nov 9 – 16

G$32,861 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 325 reviews

The Suite Life! Permit Number#SVR22-078

Sep 28 – Oct 5

G$28,320 GYD per night

Guest favorite

Cottage in Calistoga

4.9 out of 5 average rating, 421 reviews

Luxury Cottage in Downtown Calistoga, Napa Valley

Jul 8 – 15

G$82,617 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 house rentals in St. Helena have wifi?
Absolutely! We offer over 70 house 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 self check-in, over 10 homes with a bbq area, over 70 homes with wifi, 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

Villas

Popular amenities for St. Helena vacation rentals

Stay near St. Helena's top sights

Other great vacation rentals in St. Helena

Home in Calistoga

Home in Napa

Home in Glen Ellen

Home in Sonoma

Home in Glen Ellen

Home in Napa

Home in Napa

Home in Napa

Other great vacation rentals in St. Helena

Guesthouse in Glen Ellen

Condo in Napa

Apartment in Santa Rosa

Guest suite in Glen Ellen

Guesthouse in Healdsburg

Guesthouse in Sonoma

Guest suite in Santa Rosa

Cottage in Calistoga

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 house 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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