Holiday houses in Picton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Picton

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

1 of 1 pages1 / 1
Top Guest favourite
A bright living area features a comfortable grey sofa adorned with decorative pillows. A light wood coffee table sits on a geometric area rug, accompanied by a stylish chair. Natural light floods the space through the windows, highlighting the neutral decor.
Home in Prince Edward
4.99 out of 5 average rating, 199 reviews

A Tranquil Oasis in Picton

Stride across lovingly restored softwood floors that tie main level rooms together. A thorough remodeling has produced a modern kitchen and wide open, airy spaces with neutral decor. Climb stairs at night to a quiet and romantic bedroom loft. Guests have private access to the top 2 floors of the house. The 2nd floor welcomes you with a brand new kitchen, large bedroom with queen size bed, living room with queen size sofa bed, bathroom and dining room. Enjoy your breakfast (or a glass of wine) on the balcony in the summer. Take the stairs to the third floor, where you will find a private giant master bedroom loft, complete with king size bed and 2 skylights for gazing at the starry sky. Lots of room for your cars! Upon arrival, rest assured that there will always be room for up to 3 cars in the driveway (along with free street parking). Brand new kitchen is fully stocked and includes a washer/dryer for your use. Large bathroom with bathtub. Dining room with table for 6. Living room with large Smart TV with cable and sofa bed with queen size pull out. Stairs lead to the private (with door) master bedroom loft. Comfy king size bed, 2 skylights and lots of books The house is on a friendly street in the town of Picton, Prince Edward County. It was purchased on a whim by a couple who fell in love with the area. Walk downtown to fine restaurants and shops. Sandbanks Provincial Park is a 15-minute drive away. Because the house is on the top 2 floors - it is important that you and your guests (including children) are OK with stairs. We do not have baby gates. Home access is keyless via smart lock.

Top Guest favourite
Home in Prince Edward
4.94 out of 5 average rating, 379 reviews

Picton PEC Treetops Cottage 2 bed 2 bath house

ST-2019-0273 Renovated 1880s carriage house, 2 beds, 2 baths. Private yard on a quiet street in the heart of Picton, 5 min. walk to the County's finest restaurants, brewpubs, shops, and galleries; 12 minutes by car to Sandbanks' beaches. Surrounded by trees and facing 500 acres of green space, including the historic Glenwood Cemetery, Treetops is a 2-minute walk to the Millennium Trail, a 46 km route for walking and biking. The wineries a drive away, Treetops Cottage is at the heart of PEC.

Top Guest favourite
A private back patio features a wooden deck with comfortable seating arrangements, including bright cushions and decorative plants. An umbrella provides shade over the seating area, while the surrounding wooden fence enhances the cozy ambiance.
Home in Prince Edward
4.92 out of 5 average rating, 178 reviews

Harbour Main playful century home w/ private patio

Enjoy a stylish experience at this centrally located home. HarbourMain is perfectly located steps away from Picton's Main street which has lovely cafés, local shops, breweries & restaurants. No need to take the car, you can leave it parked in the back parking lot of the home (fits 2 cars comfortably) and walk to your nearby destination. The private back patio offers great seating area & BBQ. We can't wait to host you This home is fully licensed per Prince Edward County bylaws (ST-2022-0073)

Top Guest favourite
Home in Prince Edward
4.92 out of 5 average rating, 115 reviews

Downtown Picton Retreat |Near Sandbanks & Wineries

Stay in the heart of Picton - steps to downtown restaurants, The Royal, The CAPE, and everything Prince Edward County has to offer. Escape to our bright, sun-filled, stylish home on a peaceful street. This 3-bed, 2-bath chalet sleeps 6. Features a fully equipped kitchen, fireplace, and a private backyard with BBQ, patio, and fire pit. Minutes to Sandbanks Provincial Park, wineries, and breweries. You’re at the center of it all. Perfect for families, couples, and groups to relax and unwind.

Top Guest favourite
The interior features a warm wooden aesthetic with high cathedral ceilings supported by exposed beams. A staircase leads to an upper level. The chef's kitchen includes a tiled countertop with a vase of flowers, while the dining area is visible in the background.
Home in Prince Edward
4.94 out of 5 average rating, 279 reviews

Stunning Prince Edward County Post & Beam Retreat

Welcome to Three Keys Waupoos, the County's ideal luxury accommodation for those who are looking for elegance, beauty, and comfort. This retreat is situated in the the heart of all things that make the County memorable; wineries, orchards, cheese factories, and scenic vistas. The house is all about open spaces and beautifully constructed post and beam craftsmanship. A short drive to many desirable County destinations, you'll be happy you chose our house overlooking Smith's Bay, Lake Ontario!

Top Guest favourite
The open-concept guest house interior features a spacious sleeping area with a large bed. Natural light enters through sliding glass doors and tall windows, illuminating warm wooden beams and light-colored walls. A cozy seating area with two chairs and a table is visible, complemented by decorative plants.
Guesthouse in Bloomfield
4.99 out of 5 average rating, 145 reviews

The Bloomfield Guest House

Are you looking for an awe-inspiring, peaceful, retreat-like setting for your visit to The County? Book this well-crafted private guest-house in charming Bloomfield, perfectly located between Wellington and Picton. The expansive farm-field view will instantly ground and settle your being. Every aspect of this luxury offering has been designed and built with integrity and care. We welcome you to embody a felt-sense of coming home. Follow us @thebloomfieldguesthouse Licence # ST-2022-0076

Top Guest favourite
A bright living area features a grey sofa, accented by patterned cushions, and a glass coffee table on a light rug. A dark green chair adds contrast, while a flat-screen TV is mounted on the wall opposite. Natural light filters in through a window, complemented by indoor plants.
Guest suite in Prince Edward
4.98 out of 5 average rating, 187 reviews

The Huxley - cool, stylish private suite & hot tub

The Huxley is a newly renovated, private lower level suite of an idyllic Century home, in the heart of Picton. Just a short stroll to the main street and you find restaurants like The Royal Hotel, 555 Brewing and Bocado. Kick back and relax in the space designed for luxurious comfort, enjoy the MCM and antique touches through out, plus the newly installed salt water hot tub. The Huxley is the perfect spot for two adults or a family of three to have fun, reconnect and enjoy The County.

Top Guest favourite
A bright living room features a white couch complemented by a blue accent chair. Decorative plates adorn a blue wall, while a staircase with wooden railings leads to the upper level. Natural light filters through sheer curtains, illuminating the polished wooden floor.
Townhouse in Prince Edward
4.97 out of 5 average rating, 126 reviews

Private & charming historic suite, central Picton

ST-2022-0107 Enjoy easy access to everything the County has to offer from this central suite in Picton. Situated near the harbour, downtown and the hiking trails at McCauley Mountain, start the day with a hike and easily stroll home at night from Main St restaurants. This historic space is renovated with modern touches, but with the charm intact. The kitchen's well equipped for preparing meals at home and there's hidden laundry in the dining area to clean up after a day at the beach.

Guest favourite
A welcoming living area features sunlight streaming through large windows. Colorful seating includes a green armchair and an iconic yellow chair, complemented by a stylish side table. A houseplant adds a touch of greenery, and a message board is ready for personalized notes.
Apartment in Prince Edward
4.84 out of 5 average rating, 133 reviews

Funky studio Apt Full kitchen 5 min to Main St

Welcome to our renovated Mid Century Modern private studio apartment. Designed for comfort, functionality and convenience, featuring unique colorful furnishings offering you an alternative hotel stay. The apt is fully equipped for your comfortable stay, featuring a queen bed, full kitchen with new appliances, including a full size stove, microwave and fridge/freezer to accommodate your extended stay. You have your own full private bathroom with walk-in shower and in-suite laundry

Top Guest favourite
A spacious deck features red Adirondack chairs positioned for lake views, overlooking calm waters at sunset. The horizon captures warm tones, while the reflection on the water creates a serene ambiance. Clear railing allows uninterrupted sightlines of the scenic surroundings.
Cottage in Prince Edward
4.96 out of 5 average rating, 183 reviews

Picton Bay Hideaway

Picton Bay Hideaway is a family owned and operated licensed waterfront bungalow with 2 bedrooms and a walk out basement that can comfortably sleep up to 4 adults plus 2 children. This getaway is ideal for those wanting to slow down, relax and spend quality time with loved ones or for those who are looking for a quiet and peaceful workspace retreat. Whether you are a wine, food, fishing, or a beach goer, there is something for everyone in Prince Edward County (PEC)!

Top Guest favourite
The bedroom features a cozy queen bed dressed in soft linens, paired with a decorative throw. A charming nightstand stands beside the bed, and a vintage dresser is positioned across from a window, allowing natural light to illuminate the space.
Home in Prince Edward
4.97 out of 5 average rating, 148 reviews

Steps to Main St. Century Home w Sandbanks Pass

THE NESTLED INN is half a block to Picton Harbour in one direction, Delhi Park in the other, and a 2 minute walk to the many bars, cafes, and restaurants on Main Street. You couldn't ask for a better location! Enjoy the views of Macaulay Mountain from our back deck, complete with outdoor dining for six and a bbq, or stretch out in our very private, spacious back yard. Check out our Airbnb Guidebook for more recommendations. STA license number st-2020-0309

Top Guest favourite
Guest suite in Prince Edward
4.97 out of 5 average rating, 170 reviews

Romantic PEC getaway w gas fireplace & soaker tub

Modern and Spacious 2 bdrm Carriage House Loft with high-speed wifi and large, private elevated outdoor living space overlooking the treetops of Benson park. Live like a local and enjoy all the convenience of downtown village life with this walk-able location steps from the Royal Hotel. This home is a safe space for folks from all minority and marginalized groups. We welcome guests of all races, faiths, genders, and sexual orientations. ST-2020-0151 R2

Popular amenities for Picton holiday rentals

Quick stats about holiday rentals in Picton

  • Total holiday rentals

    Explore 220 holiday rentals in Picton

  • Nightly prices starting at

    Picton holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 21,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Picton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Picton rentals

  • 4.9 Average rating

    Picton stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. Canada
  3. Ontario
  4. Prince Edward County
  5. Prince Edward
  6. Picton