Book Holiday Homes in Picton

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Featured Holiday Homes in Picton

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!
✨️ Spacious Lakeview Retreat in Scenic Wine Country ✨️

✨️ Spacious Lakeview Retreat in Scenic Wine Country ✨️

Carrying Place ON
Located in Quinte West, this vacation home is a 1-minute drive from Lake Ontario and 7 minutes from Barcovan Golf Club.
Opens in a new window✨️ Spacious Lakeview Retreat in Scenic Wine Country ✨️
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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
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$444 per night from 6 Jan to 7 Jan
AU$444
6 Jan - 7 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
Main house #- 2 minutes to the lake with pool & playground -close to Sandbanks

Main house #- 2 minutes to the lake with pool & playground -close to Sandbanks

Prince Edward ON
With a stay at this vacation home in Prince Edward, you'll be within a 5-minute drive of Harwood Estate Vineyards and Hillier Creek Estates.
Opens in a new windowMain house #- 2 minutes to the lake with pool & playground -close to Sandbanks
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
Freshly Renovated 2 bedroom house with big patio and backyard

Freshly Renovated 2 bedroom house with big patio and backyard

Quinte West ON
The price is AU$365 per night from 18 Dec to 19 Dec
AU$365
18 Dec - 19 Dec
includes taxes & fees
A stay at this vacation home places you in the heart of Quinte West, within a 15-minute walk of Duncan McDonald Memorial Gardens Ice Skating Rink and Lake ...
Opens in a new windowFreshly Renovated 2 bedroom house with big patio and backyard
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
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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.

Picton 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 Picton vacation homes are the perfect way for you to wing it.

Holiday houses in Picton 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 Picton 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 Picton adventures, obvs.

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

Picton Holiday Homes essential information

Accommodation
275 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$444
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!, ✨️ Spacious Lakeview Retreat in Scenic Wine Country ✨️, Old Milford - Modern Home 5 Minutes from Picton, Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game, Main house #- 2 minutes to the lake with pool & playground -close to Sandbanks, Cape Cod style home in the heart of the lakeside village of Wellington, Freshly Renovated 2 bedroom house with big patio and backyard, Charming House in Wellington

Top trending hotels in Picton

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 24 Dec to 25 Dec
AU$163
24 Dec - 25 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
Cribs On The Hill

Cribs On The Hill

4 out of 5
5 Richmond Street Prince Edward ON
The price is AU$230 per night from 18 Dec to 19 Dec
AU$230
18 Dec - 19 Dec
includes taxes & fees
Located in Prince Edward, Cribs On The Hill is near the beach, a 4-minute walk from Macaulay Mountain Conservation Area and 9 minutes by foot from Regent ...
Opens in a new windowCribs On The Hill
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Cribs on Main

Cribs on Main

3 out of 5
289 Main Street Prince Edward ON
Fully refundableReserve now, pay when you stay
The price is AU$268 per night from 4 Jan to 5 Jan
AU$268
4 Jan - 5 Jan 2026
includes taxes & fees
When you stay at Cribs on Main in Prince Edward, you'll be in a shopping district, just steps from Regent Theatre and 11 minutes by foot from Lake Ontario.
Opens in a new windowCribs on Main
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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.