Holiday houses in Oakville

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Top-rated holiday rentals in Oakville

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Top Guest favourite
Condo in Napa
4.99 out of 5 average rating, 494 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
4.9 out of 5 average rating, 125 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.

Guest favourite
A spacious bedroom features a king-size bed with a wooden headboard, complemented by nightstands and lamps on either side. Two crisp white chairs with decorative pillows are positioned around a round wooden table, enhancing the light, airy atmosphere created by multiple windows.
Guest suite in Sonoma
4.96 out of 5 average rating, 777 reviews

Romantic Wine Country Retreat with Hot Tub

Romantic 1-bedroom guest suite with king bed, private fenced yard, and exclusive hot tub—with no shared space and private entry. Dedicated workspace, reserved parking, modern amenities. A 5-minute drive to Sonoma Plaza restaurants, wineries, shops. Minutes to vineyards, 45 minutes to Sonoma Coast. Ideal for couples seeking privacy, comfort, and authentic wine country experiences. Perfectly positioned for harvest season, holidays, barrel tastings, and romance. Permit ZPE15-0391 Quiet time 9pm-7a

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, 251 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, 200 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
A spacious living room features large windows allowing natural light to fill the space. Comfortable seating is arranged around a circular coffee table, which holds magazines. A gas-powered fireplace adds warmth, complemented by greenery from nearby plants.
Apartment in Napa
4.99 out of 5 average rating, 405 reviews

Mendez On Main #1 King Bed/10min walk to downtown

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.

Guest favourite
A scenic view captures the studio and main house nestled among greenery. A mature olive tree stands prominently in the foreground, while the surrounding landscape features gentle hills and a gravel pathway that leads to the properties.
Guesthouse in Sonoma
4.93 out of 5 average rating, 194 reviews

Cozy Sonoma Studio Nearby Wineries and Restaurants

Our super cozy Sonoma studio nestled on a twelve acre parcel has a welcoming living area, a comfortable king size bed, kitchen, and a recently refreshed bathroom. Self check in for privacy and social distancing. Home is cleaned and disinfected for 24 hours between guests, including all surfaces, sheets, towels, bedspreads, etc. This studio is a perfect wine country retreat, located about 4.4 miles from Sonoma Square, 3.7 miles to Glen Ellen, and surrounded by a multitude of wineries.

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, 595 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 private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.
Condo in Napa
4.99 out of 5 average rating, 100 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 spacious bedroom features a king bed adorned with a floral-patterned duvet. Natural light fills the room through multiple windows, with a cozy seating area visible. A flat-screen TV hangs on the wall, and a mini kitchen is positioned nearby, complemented by a small dining table.
Guesthouse in Glen Ellen
4.92 out of 5 average rating, 580 reviews

Glen Ellen Hideaway

One block to downtown Glen Ellen, with dining, shopping, & wine tasting. Hideaway is a charming, private guest house, suite-style behind our home. Spa-like bath, mini kitchen, comfy king bed! There is a large private patio for your enjoyment, great place to relax. Glen Ellen Hideaway is peaceful & private & has a separate entrance for your accommodations. Residents are Constance & Greig, and Franny, the dog, and Charm, the cat!-TOT#2398

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, 533 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.

Superhost
The entrance to a cave spa is framed by lush blooming plants, with stone walls and a wooden door. A sign announces 'Estate Cave - Spa Terra - Trinitas Tasting Room' above an arched entrance, complemented by a bench and vibrant flowers in the foreground.
Apartment in Napa
4.83 out of 5 average rating, 109 reviews

Getaway in Napa! Bowling, Spa and More all Open!

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. • 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 paid at check-in • Name on reservation must match photo ID at check-in

Popular amenities for Oakville holiday rentals

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