Book Holiday Homes in Waupoos

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Featured Holiday Homes in Waupoos

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 ON
With a stay at this vacation home in Prince Edward, you'll be within a 15-minute drive of Sandbanks Provincial Park and Regent Theatre.
Opens in a new windowHistoric Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms
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 ON
With a stay at this vacation home in Prince Edward, you'll be just steps from Wellington Heritage Museum and Lake Ontario.
Opens in a new windowSpacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!
Old Milford - Modern Home 5 Minutes from Picton

Old Milford - Modern Home 5 Minutes from Picton

Prince Edward Ontario
Located in Prince Edward, this vacation home is within a 5-minute drive of Birdhouse City and PRZ Paintball.
Opens in a new windowOld Milford - Modern Home 5 Minutes from Picton
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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 ON
The price is AU$440 per night from 12 Jan to 13 Jan
AU$440
12 Jan - 13 Jan 2026
includes taxes & fees
With a stay at this vacation home in Prince Edward, you'll be a 4-minute walk from Picton Harbour and 6 minutes by foot from Macaulay Mountain Conservation ...
Opens in a new windowGorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game
Cape Cod style home in the heart of the lakeside village of Wellington

Cape Cod style home in the heart of the lakeside village of Wellington

Wellington ON
A stay at this vacation home places you in the heart of Prince Edward, steps from Wellington Main Street Park and Lake Ontario.
Opens in a new windowCape Cod style home in the heart of the lakeside village of Wellington
Charming House in Wellington

Charming House in Wellington

Prince Edward ON
With a stay at this vacation home in Prince Edward, you'll be a 2-minute walk from Armstron Glassworks and 5 minutes by foot from Lake Ontario.
Opens in a new windowCharming House in Wellington
Relax in Style & Comfort in South Bay, PEC

Relax in Style & Comfort in South Bay, PEC

Prince Edward ON
The price is AU$433 per night from 21 Dec to 22 Dec
AU$433
21 Dec - 22 Dec
includes taxes & fees
With a stay at this vacation home in Prince Edward, you'll be steps from Lake Ontario and a 3-minute drive from Little Bluff Conservation Area.
Opens in a new windowRelax in Style & Comfort in South Bay, PEC
The Stanley | Bloomfield | 3 Bedrooms | Hot Tub

The Stanley | Bloomfield | 3 Bedrooms | Hot Tub

Prince Edward ON
With a stay at this vacation home in Prince Edward, you'll be within a 15-minute drive of Sandbanks Provincial Park and Bloomfield Visitor's Centre.
Opens in a new windowThe Stanley | Bloomfield | 3 Bedrooms | Hot Tub
The Ferg Garden Suite | Picton | 1 Bedrooms

The Ferg Garden Suite | Picton | 1 Bedrooms

Prince Edward ON
With a stay at this vacation home in Prince Edward, you'll be within a 15-minute drive of Sandbanks Provincial Park and Regent Theatre.
Opens in a new windowThe Ferg Garden Suite | Picton | 1 Bedrooms
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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
210 Holiday Homes
Lowest Price
AU$125
Highest Price
AU$440
Popular accommodation
Historic Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms, Spacious 3-bedroom Home in Downtown Wellington with in Ground Pool and parking!, Old Milford - Modern Home 5 Minutes from Picton, Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game, Cape Cod style home in the heart of the lakeside village of Wellington, Charming House in Wellington, Relax in Style & Comfort in South Bay, PEC, The Stanley | Bloomfield | 3 Bedrooms | Hot Tub, The Ferg Garden Suite | Picton | 1 Bedrooms

Top trending hotels in Waupoos

Picton Harbour Inn

Picton Harbour Inn

3 out of 5
33 Bridge Street Prince Edward ON
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 30 Dec to 31 Dec
AU$163
30 Dec - 31 Dec
includes taxes & fees
With a stay at Picton Harbour Inn in Prince Edward, you'll be within a 5-minute walk of Picton Harbour and Regent Theatre.
Opens in a new windowPicton Harbour Inn
The Waring House

The Waring House

3 out of 5
395 Sandy Hook Road 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
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
31 Community Road Greater Napanee ON
Fully refundableReserve now, pay when you stay
The price is AU$125 per night from 4 Jan to 5 Jan
AU$125
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Comfort Inn & Suites in Napanee, you'll be within a 5-minute drive of Canadian Piano Museum and Strathcona Paper Centre.
Opens in a new windowComfort Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Huff Estates Inn & Winery

Huff Estates Inn & Winery

3 out of 5
2274 County Rd #1 Prince Edward ON
Fully refundableReserve now, pay when you stay
The price is AU$289 per night from 28 Dec to 29 Dec
AU$289
28 Dec - 29 Dec
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
Don't see what you're looking for?
See all available properties in Waupoos
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.