Holiday houses in Oakville

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Top-rated holiday rentals in Oakville

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Top Guest favourite
The image showcases a scenic view of the Silverado Resort grounds, featuring well-maintained grassy areas and a sparkling pool surrounded by trees. The backdrop includes distant mountains and a clear blue sky, providing a tranquil outdoor setting.
Condo in Napa
4.99 out of 5 average rating, 488 reviews

Silverado! Luxe 1BR King Suite This 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.

Top Guest favourite
A modern living room features a sleek gray sofa paired with a glass coffee table on a light area rug. Subtle wall accents and a cozy fireplace enhance the space, while large windows allow natural light to fill the room.
Condo in Napa
4.99 out of 5 average rating, 250 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

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, 199 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.

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, 413 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
A spacious living area features a modern wall-mounted television and comfortable seating arrangements. A stylish coffee table sits at the center, surrounded by a large area rug. Decorative elements include a plant and artwork, adding a subtle touch to the neutral color palette.
Home in Napa
5 out of 5 average rating, 165 reviews

A Wine Travelers Dream in the Heart of Napa Valley

✨Welcome to our beautiful Napa Valley home, perfectly situated between the vibrant energy of downtown and the breathtaking beauty of the Valley. 6 minutes to downtown Napa, 5 minutes to Silverado trail, 20 minutes to Sonoma. Indulge in the world-class restaurants, vibrant nightlife of downtown, or venture into the valley to explore the rolling hills and picturesque landscapes that have made this region famous. After a day of adventure, retreat to our ample space to rewind and rejuvenate.✨

Top Guest favourite
The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.
Villa in Napa
4.96 out of 5 average rating, 182 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!

Top Guest favourite
The exterior of a charming home is captured at dusk, featuring a lush lawn and landscaped garden. Decorative lighting illuminates the pathway, leading to the entrance. A rock garden with vibrant flowers is visible, enhancing the tranquil ambiance of the property.
Home in Napa
4.94 out of 5 average rating, 437 reviews

Charming Napa home with Wine Tour. VR16-0011

Come stay at this lovely Napa home. Recently updated with beautiful amenities...minutes from Downtown Napa. Close to amazing restaurants and shops! Home is fully furnished, beautifully updated, including flat screens, great WiFi, W/D, D/W and all amenities of home. Parking/ cable included. Home is very spacious and has a beautiful backyard to relax and unwind from your day in Napa Valley. Wine Tours upon request. We can set up iteneries and provide some amazing winery options!

Superhost
A comfortable living area features a light-colored sofa adjacent to a modern coffee table. Large glass doors lead to an outdoor space with views of the golf course, allowing natural light to fill the room. A fireplace adds a cozy touch.
Apartment in Napa
4.88 out of 5 average rating, 161 reviews

Napa relaxation at its finest at Silverado Resort

Relax in our remodeled 1 bedroom king bed, 1 queen sleeper sofa & 1 bath condo at Silverado Resort & Spa on the 1st & 18th Fairway on the PGA North Golf Course. Plan a meeting or just get away from it all in the beauty of Napa Valley's wine country, only 10 min by car to downtown Napa, world class wineries & 5 star restaurants. Amenities include access to association pool, cocktail lounge, restaurants, pizza lounge, coffee lounge & market. Carport parking for one car included

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, 593 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!

Guest favourite
A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.
Cabin in Occidental
4.97 out of 5 average rating, 579 reviews

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

Top Guest favourite
The spacious bathroom features a modern dual-sink vanity with a large circular mirror above. A freestanding bathtub is positioned beside a natural light-filled window, with greenery adding a touch of nature. A glass shower enclosure is visible, complemented by stylish overhead lighting.
Apartment in Napa
4.97 out of 5 average rating, 529 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.

Top Guest favourite
A classic white house with a welcoming front porch is framed by lush greenery and mature gardens. The well-maintained pathway leads to grand double doors, inviting guests into a historic home rich in character and charm.
Home in Napa
4.96 out of 5 average rating, 300 reviews

Stoddard House

The Stoddard House is as rich in history as it is in appearance. Built in 1898, this classic home retains its original grandeur with mature gardens, vaulted ceilings, double parlor and Red Fir floors. Not your average vacation rental, this house is exceptional in every way adding to your memorable wine country experience. City of Napa Vacation Rental Permit #VR09-0048. Business Lic # 27743.

Popular amenities for Oakville holiday rentals

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