Holiday houses in Port Milford

Modern School House *SPA GETAWAY*HOT TUB & SAUNA*

​Welcome to the Schoolhouse, an 1859 original school remodelled for your boutique vacation getaway. Located on Glenora Road just a few minute drive from the glorious downtown shops & restaurants of Picton Main St. The central location also acts as a great jumping off point to enjoy all the spectacular wineries, craft breweries, art galleries, beaches & trails that the County has become known for. *Please note we are a family getaway and not set up to host those looking for a party atmosphere*

Waterfront Casa in wine County w/SAUNA and HOT TUB

Escape to this beautifully updated lakefront home on 170ft of private shoreline in beautiful Prince Edward County. Enjoy our new panoramic view sauna, hot tub and outdoor shower. This relaxing getaway is located on the Bay of Quinte, just 2hrs east of Toronto. A 30 min drive to Sandbanks, 20 mins to Picton/Wellington. Close to many wineries and breweries. Large yard space makes this an ideal home for groups, couples and families looking for postcard views and private spa amenities. ST-2023-0002

South Bay Lakehouse. 4 acres - Waterfront!

Summer Dates now Open! 16 minutes south of Picton is the picturesque enclave of South Bay. Serene farmlands, vineyards and pristine waterfront make this a stunning part of the County. The home sits on 4 acres with 400 ft of waterfront. You'll be a short drive from everything but miles away from the hustle and bustle of city life. This place is great for couples, small families, nature enthusiasts or anyone looking for a peaceful spot with spectacular sunsets :) License # ST - 2020 - 0067

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!

The Disco Garden Party by The Post Office Motel

Imagine arriving at a secluded mid-century modern retreat, where design and comfort both take first place. You sink into the warmth of your private hot tub, the sky above unfolding into a blanket of stars. Tonight, the Milky Way puts on a show just for you. Later, laughter fills the air as you gather around the fire pit, roasting gooey s’mores with family and friends. Located just minutes to secret speakeasy bars and wine lounges, wineries, the Mustang Drive-In and Sandbanks Provincial Park!

Spectacular Waterfront Home in PEC

Situated on the edge of the beautiful Bay of Quinte, this brand new modern build is sure to steal your breath. Built in 2023, this stunning two-storey waterfront oasis, Water’s Edge, is located just over the Bay Bridge in spectacular Prince Edward County. Featuring two kayaks, fishing gear, outdoor propane fire table, and an upper and lower deck with front row seats to the most unforgettable sunsets. Water’s Edge is conveniently located to both Belleville and all that PEC has to offer.

Westlake's Suite 25

A beautiful self contained Suite WITHIN our home with self check in. A sitting room with kitchenette, leading into a separate spacious bedroom with ensuite. The large windows allow for an abundance of natural light throughout. Relax and reflect on the front porch. Located in Westlake, which is approx. 15 minutes from downtown Picton. parking included. Walking distance, approx 1.3 km, to the Dunes beach at Sandbanks prov. Park.. Sandbanks parking pass included Occupancy 2 adult

HALF PRICE FOR JUNE:Private lake house with beach

25 min to Sandbanks Prov Park. Seasonal park pass provided Private south facing Lake Ontario beach. Large deck with BBQ overlooks huge yard and beach. Pagoda and beach fire pits. Security system (no cameras), 2 car garage, large parking area Property manager on call 24/7 We live in a isolated area surrounded by wildlife, including the potential for coyotes, ants or mice. While we make every effort to minimize any concerns, please bring any issues to our prompt attention

Peaceful Peninsula. A Private Waterfront Oasis.

Please note summer 2026 (June 20-August 28) is weekly rentals Friday to Friday. Come and unwind on a private peninsula with water surrounding you on 3 sides. Peaceful peninsula is the perfect private, tranquil getaway. A place for mind, body and soul to find rest. NEW! CEDAR BARREL SAUNA with panoramic views, hot tub, seasonal outdoor shower, wood stove, 2 outdoor fire pits and a day bed in the gazebo all provide ample opportunities for relaxation. ST-2020-0226

Demilune Lodge - Serene cabin with hot tub

Get away to a feeling of relaxation, cozy, and colourful living in this eclectic log cabin set among the abundant wildlife of South Bay, Prince Edward County. Add stargazing, bird watching (only 20 minutes from the bird observatory on Long Point Rd), and hot tubbing to your to-do list PLUS all the winery and beach hopping that comes with being in beautiful PEC. This home is fully licensed per Prince Edward County bylaws (ST-2022-0044).

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

The Walmsley House STA License #ST-2020-0255

Located on the outskirts of Milford, this 100 year old farm house is cozy and perfect for a weekend getaway, or a family vacation. It is a fifteen minute drive to Sandbanks Provincial Park, great dining, wineries, restaurants, and shops. Book a farm tour with the Miller Family on their Dairy Farm, which is within walking distance. You will love the seclusion and peacefulness of Maypullayn.