Holiday houses in Oakville

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Top-rated holiday rentals in Oakville

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

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Top Guest favourite
Condo in Napa
4.99 out of 5 average rating, 499 reviews

Silverado! Luxe King Suite Mountain View Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from balcony, living and dining rooms. Wood burning fireplace. *Price incl tax. Walk to pool, market, dining, lounge at mansion. Modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette on King bed. Just like a 5-star hotel. Roku streaming,Directv Hang out or walk in relaxing grounds! La-Z-Boy queen sofabed, Aug 2025. Free L2 EV chargers nearby.

Guest favourite
Two turquoise chairs are positioned near a serene creek, surrounded by lush greenery. The water reflects the surrounding trees, creating a calm and tranquil atmosphere. A wooden deck of a nearby cabin is visible above, adding to the natural setting.
Cottage in Glen Ellen
4.91 out of 5 average rating, 128 reviews

Cozy Sonoma Creekside Escape: Couples Retreat

Peaceful retreat in Glen Ellen, right on Sonoma Creek. Sleep to the sound of bubbling water! 1BR/1BA with a full kitchen, smart TV, washer/dryer, big office, and fast Wi-Fi. Relax on the deck with creek views, BBQ, and loungers. Pet-friendly, self check-in and great restaurants. Close to wineries and hiking. Perfect for couples, digital nomads, and nature lovers. You're just minutes from wineries, scenic hikes, and the charm of Glen Ellen — but you might find it hard to leave this peaceful spot.

Top Guest favourite
A serene courtyard features a circular firepit surrounded by four wicker chairs, inviting relaxation. Sunlight filters through the trees, creating a warm ambiance. Lush greenery and a vineyard view extend beyond the enclosure, enhancing the tranquil outdoor space.
Guest suite in Napa
4.96 out of 5 average rating, 202 reviews

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

Enjoy our vineyard view and a glass of wine by the firepit! Relax in our ONE BEDROOM SUITE, ON THE LOWER LEVEL OF OUR TRI-LEVEL HOME. Conveniently located in N. Napa, we're near Alston Park for hiking, wineries, places to eat & shop. Enjoy a fresh-baked BREAKFAST, a dip in the pool (heated mid-June to Sept), spa (year-round) & many places for relaxing. Our suite is well appointed with a comfortable bed, fine linens, duvet, robes & slippers. DRIVING SERVICES may be added to enhance your tours.

Guest favourite
Condo in Napa
4.94 out of 5 average rating, 121 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

Welcome to Casa Vina! Located in one of the best locations at Silverado, close to the HOA pool, Grill and baked goods from the Market, this end unit cottage has golf course and mountain views, a wood burning fireplace and no one upstairs. Updated with mid-century West Elm furniture, 55" TV, enlarged shower, Casper Mattress, stainless steel kitchenette and Keurig coffee maker, this is one of the nicest junior suites at Silverado. Discounted spa day passes available for purchase, when available.

Top Guest favourite
The living room features a comfortable gray sofa and two elegant armchairs surrounding a wooden coffee table. Natural light fills the space through large windows. A dining area is visible through an open doorway, with a plush bed and decorative wall art adding to the atmosphere.
Apartment in Napa
4.99 out of 5 average rating, 418 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.

Top Guest favourite
Condo in Napa
4.99 out of 5 average rating, 214 reviews

Silverado 1BR Condo | Walk to Pool

Soak up sunny days at Silverado Resort, perfectly located near Napa Valley’s top wineries and attractions. This light-filled condo features two king beds, a well-equipped kitchen, cozy fireplace, and a balcony overlooking the pool—ideal for morning coffee or an evening glass of wine. Enjoy resort dining, pools, Tesla charging, on-site laundry, and more. Guests love the spotless space, coastal-inspired decor, and responsive host—a perfect spring escape in the heart of Wine Country.

Top Guest favourite
Home in Sonoma
4.96 out of 5 average rating, 520 reviews

A sophisticated Wine Country Cottage with Hot tub

Escape to Thornsberry Cottage, a luxe wine country retreat 5 mins from Sonoma Square. This unique property features two separate cottages, each with a private bed/bath, perfect for guests seeking privacy and togetherness. Enjoy vaulted ceilings, a large deck, a private hot tub, and a fire pit under ancient oaks. 5 minutes from the Sonoma Square, 3 minutes to the oldest wineries in California, or walk or bike to Gundlach Bundschu at the end of our road. Your serene getaway awaits!

Top Guest favourite
A cozy bedroom features a spacious bed with a light-colored duvet and decorative green pillow. Natural light enters through the window with wooden blinds. A small TV is positioned on a nearby barrel, and a sliding door leads to a closet with hanging space.
Guesthouse in Napa
4.94 out of 5 average rating, 600 reviews

Kats Place Napa Valley Walk Downtown VR-16-0044

The home is a 2 minute drive or 15 minute walk to downtown Napa and an abundance of shopping and great restaurants. Attached Duplex unit - Private guest house with full kitchen, bathroom , living room , backyard , bedroom and off street parking area. comfortable and conveniently located right off the Silverado Trail in the heart of Napa Valley's world-renown wineries. I would be happy to help with any of your travel plans. Certified Vacation Rental VR16-0044. Cheers!

Top Guest favourite
A spacious guest suite features a large bed adorned with decorative pillows and a mustard-colored throw. Natural light fills the room through windows, complemented by a ceiling fan. A dining table with chairs and a round mirror add to the welcoming atmosphere.
Guest suite in Sonoma
5 out of 5 average rating, 187 reviews

Enchanting KING Wooded Sanctuary ‘Fawns Creek’

FAWNS CREEK IN WINE COUNTRY is a tranquil & private hideaway. The modern farmhouse decor is intended to help you relax and unwind the moment you step inside. (No pets & No children please 😉) Songbirds will be your alarm clock in the morning. Hummingbirds, squirrels & deer will visit you all day. Owls, crickets & frogs will sing you a lullaby. Toss some sausages on the gas grill & dine al fresco. Click on the gas fire table & wrap up in a blanket under the stars.

Top Guest favourite
Condo in Napa
4.99 out of 5 average rating, 102 reviews

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

✨✨ Welcome to Your Modern Napa Stay! ✨✨ Discover the perfect blend of luxury and comfort in our stunning 2 bed, 2 bath spacious space. This contemporary retreat features stylish decor, an open-concept living space, ideal for relaxing after a day of exploring the beautiful wineries and vibrant culinary scene. Whether you're here for a romantic getaway, a trip with friends, or a family vacay, our modern Napa retreat offers everything you need for a memorable stay!

Guest favourite
A modern living area features a leather sofa with two decorative pillows, a clear coffee table, and a geometric area rug. A stylish dining table sits nearby, while the kitchen is visible in the background, showcasing sleek cabinetry and open shelving.
Condo in Napa
4.97 out of 5 average rating, 215 reviews

Luxe 1BR Condo Par Excellence at Silverado Resort

Experience the allure of Napa Valley in this sleek condo at Silverado Resort. Enjoy modern comforts and amenities in a stunning setting perfect for a romantic escape, a fun getaway with friends, or a peaceful retreat after wine tasting. Just 10 mins from downtown Napa, with wineries nearby and many more within a 15-min drive. Luxuriate in the modern design, a plush King bed with bamboo linens, and two electronic fireplaces for a cozy ambiance.

Top Guest favourite
The exterior of a modern, wooden cottage is showcased with a welcoming front porch. Steps lead up to double French doors, surrounded by vibrant landscaping and trees. Large windows and a triangular peak create an inviting entrance, while plants line the walkway.
Cabin in Sonoma
4.99 out of 5 average rating, 546 reviews

Sonoma Berry Blossom Farm

Modern and spacious with glass enclosed porch, high ceilings and lots of French doors, skylights and windows. Close to town in the very nicest area within a mile of downtown, walkable, or bikeable with my cruiser bikes. You’ll love the views, the location, the goats, quail running around and delicious cafe next door. We just lost our mini horse 7/27 :( we had 16 years, sorry if you had planned on meeting him, it was a sad loss for us.

Popular amenities for Oakville holiday rentals

  1. Airbnb
  2. United States
  3. California
  4. Napa County
  5. Oakville