Picton Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Picton Vacation Homes

Peaceful Luxury in Prince Edward County – Hot Tub, EV Charger
Relax in the hot tub surrounded by a pergola with ambient lighting.

Peaceful Luxury in Prince Edward County – Hot Tub, EV Charger

10.0 out of 10, Exceptional, (37)
"One of our best home we rented with VRBO"
Peaceful Luxury in Prince Edward County – Hot Tub, EV Charger
The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.
Sit and enjoy the outdoors on the porch of this charming barn, surrounded by a grassy area and picnic tables.

The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.

10.0 out of 10, Exceptional, (48)
"Would love to stay again in the future :)"
The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.
Old Milford - Modern Home 5 Minutes from Picton
Relax on the outdoor patio with a light-colored sofa, wooden table, and wicker chair.

Old Milford - Modern Home 5 Minutes from Picton

8.8 out of 10, Excellent, (5)
"This rental is minutes away from Sandbanks Provincial Park. It’s a great home base for visiting the winery’s. Seven minutes away from Main Street Picton, where you can get your groceries and the LCBO. It is situated in a rural setting with lots of privacy. The unit is well layed out for a group (we were 6 adults) with three very comfortable rooms and two washrooms. Very clean and well decorated. Much larger than it appears in the photos on line. Parking for three cars, maybe four. It is situated...
Old Milford - Modern Home 5 Minutes from Picton
Entire water front house in beautiful Carrying Place.
Relax in a serene bedroom with a large bed, a small table, and a potted plant.

Entire water front house in beautiful Carrying Place.

10.0 out of 10, Exceptional, (15)
"Clean and well located house ! Would rent again !"
Entire water front house in beautiful Carrying Place.
Charming Cottage in Wellington’s Heart near Beach!
Walk along the beachside boardwalk, taking in the sights and sounds of the ocean.

Charming Cottage in Wellington’s Heart near Beach!

9.8 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay. Beautiful home and perfect location! We can't wait to visit again!!"
The price is CA $394
CA $688 total
includes taxes & fees
Aug 14 - Aug 15
Charming Cottage in Wellington’s Heart near Beach!
Grays Lane - Minutes to Sandbanks
Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and stainless steel sink.

Grays Lane - Minutes to Sandbanks

10.0 out of 10, Exceptional, (14)
"Great stay"
Grays Lane - Minutes to Sandbanks
Luxurious Vacation Retreat - Pool, basketball court, pizza oven, central in PEC
Relax by the serene pool surrounded by lush greenery and hydrangea flowers.

Luxurious Vacation Retreat - Pool, basketball court, pizza oven, central in PEC

10.0 out of 10, Exceptional, (54)
"Amazing stay and the host assistance is great! Thank you Monica"
Luxurious Vacation Retreat - Pool, basketball court, pizza oven, central in PEC
Harbour Main playful century home w/ private patio
Relax in the serene patio area with a round table, comfortable chairs, and lush greenery.

Harbour Main playful century home w/ private patio

10.0 out of 10, Exceptional, (21)
"Great location with a very short walk to the main street! Kitchen is well-equipped to make your own meals, but close enough to some nice restaurants if you prefer to eat out. Parker, the host, was very attentive in a non-intrusive way and the communication was excellent. Lots of thoughtful extras provided to ensure a wonderful stay!"
Harbour Main playful century home w/ private patio
Downtown Picton, 3 bedroom.
Enjoy cooking in this well-equipped kitchen with a double oven, microwave, and ample cabinetry.

Downtown Picton, 3 bedroom.

10.0 out of 10, Exceptional, (12)
"Spacious, clean, well-appointed property. Very comfortable stay."
The price is CA $481
CA $951 total
includes taxes & fees
Jul 21 - Jul 22
Downtown Picton, 3 bedroom.
The Kelly | 4 Bedrooms | Hot Tub
Relax in this open-plan living space with a kitchen area, featuring a central island with seating and a comfortable sofa.

The Kelly | 4 Bedrooms | Hot Tub

9.8 out of 10, Exceptional, (8)
"We enjoyed this beautiful property"
The Kelly | 4 Bedrooms | Hot Tub
The Vine House - Go to the vineyards!
Relax in a stylish living room with a large flat-screen TV, fireplace, and comfortable seating area.

The Vine House - Go to the vineyards!

The Vine House - Go to the vineyards!
The Dylan | 4 Bedrooms | 8 Guests | Hot Tub | Waterfront
Relax in this spacious living room with a large sofa, coffee table, and fireplace.

The Dylan | 4 Bedrooms | 8 Guests | Hot Tub | Waterfront

9.4 out of 10, Exceptional, (3)
"We had a great relaxing stay "
The Dylan | 4 Bedrooms | 8 Guests | Hot Tub | Waterfront
The Stanley | Bloomfield | 3 Bedrooms | Hot Tub
Enjoy a romantic meal under the stars in our serene garden setting, complete with a beautifully set table and a charming view.

The Stanley | Bloomfield | 3 Bedrooms | Hot Tub

10.0 out of 10, Exceptional, (1)
"Our family of 6 adults stayed for an extended Easter weekend at this well-appointed home that retains all of its country charm. The big back yard for our dogs and the hot tub were just two of the outdoor features that we enjoyed. The three comfortable king size beds were a bonus after long days of hiking and exploring the County. Highly recommended!"
The Stanley | Bloomfield | 3 Bedrooms | Hot Tub
The Ferg Garden Suite | Picton | 1 Bedrooms
Enjoy meals in this cozy dining area with a rustic table and comfortable seating.

The Ferg Garden Suite | Picton | 1 Bedrooms

9.8 out of 10, Exceptional, (7)
"Excellent location, close to dining and shopping. Spacious living area. Minor maintenance issues (blind closer missing, a/v needs upgrade). All considered, good value."
The Ferg Garden Suite | Picton | 1 Bedrooms
Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!
Fridge, microwave, oven, stovetop

Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!

The price is CA $495
CA $807 total
includes taxes & fees
Jul 23 - Jul 24
Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!
Sandbanks Cottage Resort Villa In Beautiful Prince Edward County
Relax by the pool surrounded by lush trees and comfortable lounge chairs.

Sandbanks Cottage Resort Villa In Beautiful Prince Edward County

9.6 out of 10, Exceptional, (14)
"We had a great stay here, would highly recommend :)"
Sandbanks Cottage Resort Villa In Beautiful Prince Edward County
Field of Dreams - Secluded w Sauna
Relax in a serene natural setting surrounded by lush greenery, with a cabin and Adirondack chairs inviting you to unwind.

Field of Dreams - Secluded w Sauna

10.0 out of 10, Exceptional, (4)
"Had an amazing stay with our friends and dogs. House was clean and location was great! Short drive to picton and wineries. Host was extremely kind and quick to respond. Big back yard gave our dogs plenty of space to run around. Will definitely be staying here next year when we come back for another wine tour!"
Field of Dreams - Secluded w Sauna
Wine Country, 4 bedrooms!
Classic charm abounds in this traditional home, featuring a welcoming porch with lush flowering plants.

Wine Country, 4 bedrooms!

10.0 out of 10, Exceptional, (2)
"We loved out stay in Wellington. The home was very cute and inviting. The only minor concern was that the home was very musty smelling on arrival (which could be problematic for those with asthma) and my young son found a dead fly and clumps of lint in his bed."
Wine Country, 4 bedrooms!
NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)
Relax in the hot tub surrounded by a cozy seating area with a fire feature and string lights.

NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)

10.0 out of 10, Exceptional, (6)
"Great place to stay! Enough beds for a larger group, has everything you need with a nice hot tub!"
The price is CA $994
CA $1,588 total
includes taxes & fees
Aug 8 - Aug 9
NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)
Royal Road Retreat ~ Cheesemaker’s Loft (sleeps 6 max)
Enjoy a serene beach experience with a pebbly shore and lush green trees.

Royal Road Retreat ~ Cheesemaker’s Loft (sleeps 6 max)

8.8 out of 10, Excellent, (11)
"Very pleasant place and not far from regional attractions. Peaceful and relaxing retreat. Note: one of the bedrooms was not private. Walk along path at back of property was nice bonus. Host was very lovely to deal with."
Royal Road Retreat ~ Cheesemaker’s Loft (sleeps 6 max)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free