Book Holiday Homes in Waupoos

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Featured Holiday Homes in Waupoos

Grays Lane - Minutes to Sandbanks

Grays Lane - Minutes to Sandbanks

Prince Edward
Located in Prince Edward, this vacation home is in a rural location, within a 10-minute drive of Caddy Shack Mini Golf and Sandbanks Provincial Park.
Opens in a new windowGrays Lane - Minutes to Sandbanks
Historic Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms

Historic Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms

Prince Edward
With a stay at this vacation home in Prince Edward, you'll be within a 15-minute drive of Sandbanks Provincial Park and Lake Ontario.
Opens in a new windowHistoric Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms
Stunning House on the Water's Edge

Stunning House on the Water's Edge

Prince Edward
With a stay at this vacation home, you'll be centrally located in Prince Edward, a 1-minute drive from Lake Ontario and 12 minutes from Prince Edward County ...
Opens in a new windowStunning House on the Water's Edge
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Old Milford - Modern Home 5 Minutes from Picton

Old Milford - Modern Home 5 Minutes from Picton

Prince Edward
With a stay at this vacation home in Prince Edward, you'll be within a 10-minute drive of Lake Ontario and Birdhouse City.
Opens in a new windowOld Milford - Modern Home 5 Minutes from Picton
Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!

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

Prince Edward
Located in Prince Edward, this vacation home is within a 15-minute drive of Lake Ontario and Prince Edward County Lavender Farm.
Opens in a new windowSpacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!
Modern 4BR Harbourfront Century Home

Modern 4BR Harbourfront Century Home

Prince Edward
With a stay at this vacation home in Prince Edward, you'll be within a 15-minute walk of Lake Ontario and Picton Harbour.
Opens in a new windowModern 4BR Harbourfront Century Home
Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game

Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game

Prince Edward
The price is AU$456 per night from 5 Nov to 6 Nov
AU$456
5 Nov - 6 Nov
includes taxes & fees
With a stay at this vacation home in Prince Edward, you'll be within a 5-minute drive of Lake Ontario and Picton Harbour.
Opens in a new windowGorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game
NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)

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

Prince Edward
With a stay at this vacation home in Prince Edward, you'll be within a 5-minute drive of Lake Ontario and Picton Harbour.
Opens in a new windowNEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)
The Demorestville: PEC Getaway

The Demorestville: PEC Getaway

Prince Edward
Located in Prince Edward, this vacation home is within a 15-minute drive of Lake Ontario and Prince Edward County Lavender Farm.
Opens in a new windowThe Demorestville: PEC Getaway
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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.

Waupoos Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Waupoos vacation homes are the perfect way for you to wing it.

Holiday houses in Waupoos let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Waupoos in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Waupoos adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Waupoos with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Waupoos vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Waupoos Holiday Homes essential information

Accommodation
303 Holiday Homes
Lowest Price
AU$176
Highest Price
AU$456
Popular accommodation
Grays Lane - Minutes to Sandbanks, Historic Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms, Stunning House on the Water's Edge, Old Milford - Modern Home 5 Minutes from Picton, Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!, Modern 4BR Harbourfront Century Home, Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game, NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes), The Demorestville: PEC Getaway

Top trending hotels in Waupoos

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

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

Prince Edward
With a stay at this vacation home, you'll be centrally located in Prince Edward, within a 5-minute drive of Lake Ontario and Waupoos Winery.
Opens in a new window The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.
The Waring House

The Waring House

3 out of 5
395 Sandy Hook Road, Picton, Prince Edward, ON
When you stay at The Waring House in Prince Edward, you'll be in the historical district, within a 5-minute drive of Mustang Picton Drive-In Theatre and Regent ...
Opens in a new windowThe Waring House
Picton Harbour Inn

Picton Harbour Inn

3 out of 5
33 Bridge Street, Picton, Prince Edward, ON
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 12 Nov to 13 Nov
AU$176
12 Nov - 13 Nov
includes taxes & fees
With a stay at Picton Harbour Inn in Prince Edward, you'll be within a 15-minute walk of Lake Ontario and Picton Harbour.
Opens in a new windowPicton Harbour Inn
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Huff Estates Inn & Winery

Huff Estates Inn & Winery

3 out of 5
2274 County Rd #1, Bloomfield, Prince Edward, ON
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 6 Nov to 7 Nov
AU$299
6 Nov - 7 Nov
includes taxes & fees
Located in Prince Edward, Huff Estates Inn & Winery is in a provincial park, a 1-minute drive from Huff Estates Winery and 7 minutes from Lake Ontario.
Opens in a new windowHuff Estates Inn & Winery
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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.

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^Subject to availability and chosen travel dates.