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Featured Holiday Homes in Wellington

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
Stay at this family-friendly holiday home in Prince Edward. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Sandbanks Provincial Park ...
Opens in a new windowCape Cod style home in the heart of the lakeside village of Wellington
Cozy House | Walk to Picton Main |Pet-friendly

Cozy House | Walk to Picton Main |Pet-friendly

Picton Ontario
The price is NZ$696 per night from 11 May to 12 May
NZ$696
11 May - 12 May
includes taxes & fees
Stay at this holiday home in Prince Edward. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Regent Theatre and Prince Eddy's Brewing Co. ...
Opens in a new windowCozy House | Walk to Picton Main |Pet-friendly
The County Stay - Bloomfield

The County Stay - Bloomfield

Prince Edward ON
Stay at this holiday home in Prince Edward. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Prince Edward County Lavender Farm and TerraCello ...
Opens in a new windowThe County Stay - Bloomfield
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10-Acre BOQ/PEC Estate, Waterfront, 3BR Ensuite & Walk-in, +1BR, Gourmet Kitchen

10-Acre BOQ/PEC Estate, Waterfront, 3BR Ensuite & Walk-in, +1BR, Gourmet Kitchen

Greater Napanee ON
Stay at this holiday home in Napanee. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Old Hay Bay Church National Historic Site ...
Opens in a new window10-Acre BOQ/PEC Estate, Waterfront, 3BR Ensuite & Walk-in, +1BR, Gourmet Kitchen
Main house 30m to Sandbanks - 2 minutes to the lake Consecon with playground

Main house 30m to Sandbanks - 2 minutes to the lake Consecon with playground

Prince Edward ON
Stay at this holiday home in Prince Edward. Enjoy a garden, laundry facilities and patios. Popular attractions Prince Edward County Lavender Farm and Harwood ...
Opens in a new windowMain house 30m to Sandbanks - 2 minutes to the lake Consecon with playground
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
Stay at this holiday home in Prince Edward. Enjoy a garden, laundry facilities and concierge services. Popular attractions Base31 and Regent Theatre are located ...
Opens in a new windowHistoric Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms
One Main Guesthouse-2 King Suites, 2 Bathrooms, 2 Floors, EV Charging

One Main Guesthouse-2 King Suites, 2 Bathrooms, 2 Floors, EV Charging

Prince Edward ON
Stay at this holiday home in Prince Edward. Enjoy free Wi-Fi, balconies and an in-room coffee maker. Popular attractions Base31 and Mustang Picton Drive-In Theatre ...
Opens in a new windowOne Main Guesthouse-2 King Suites, 2 Bathrooms, 2 Floors, EV Charging
Old Milford - Modern Home 5 Minutes from Picton

Old Milford - Modern Home 5 Minutes from Picton

Prince Edward Ontario
Stay at this holiday home in Prince Edward. Enjoy patios, an in-room coffee maker and air conditioning. Popular attractions PRZ Paintball and Birdhouse City ...
Opens in a new windowOld Milford - Modern Home 5 Minutes from Picton
The County Queen - Historic Home in Picton

The County Queen - Historic Home in Picton

Prince Edward ON
Stay at this holiday home in Prince Edward. Enjoy a garden, laundry facilities and patios. Popular attractions Regent Theatre and Prince Eddy's Brewing Co. are ...
Opens in a new windowThe County Queen - Historic Home in Picton
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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.

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

Holiday houses in Wellington 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 Wellington 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 Wellington adventures, obvs.

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

Wellington Holiday Homes essential information

Accommodation
356 Holiday Homes
Lowest Price
NZ$298
Highest Price
NZ$696
Popular accommodation
Cape Cod style home in the heart of the lakeside village of Wellington, Cozy House | Walk to Picton Main |Pet-friendly, The County Stay - Bloomfield , 10-Acre BOQ/PEC Estate, Waterfront, 3BR Ensuite & Walk-in, +1BR, Gourmet Kitchen, Main house 30m to Sandbanks - 2 minutes to the lake Consecon with playground, Historic Octagon House! Pet Friendly. Heart of Picton. 5 bedrooms/5.5 bathrooms, One Main Guesthouse-2 King Suites, 2 Bathrooms, 2 Floors, EV Charging, Old Milford - Modern Home 5 Minutes from Picton, The County Queen - Historic Home in Picton

Top trending hotels in Wellington

Lakeside Motel

Lakeside Motel

3.5 out of 5
349 Wellington Main St Prince Edward ON
The price is NZ$544 per night from 5 May to 6 May
NZ$544
5 May - 6 May
includes taxes & fees
Stay at this beach inn in Prince Edward. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowLakeside Motel
Newsroom Suites

Newsroom Suites

3.5 out of 5
269 Main Street Prince Edward ON
The price is NZ$298 per night from 25 May to 26 May
NZ$298
25 May - 26 May
includes taxes & fees
Stay at this guesthouse in Prince Edward. Enjoy free Wi-Fi, free parking and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowNewsroom Suites
Drake Devonshire and Motor Inn

Drake Devonshire and Motor Inn

4 out of 5
43 Wharf St Prince Edward ON
The price is NZ$433 per night from 11 May to 12 May
NZ$433
11 May - 12 May
includes taxes & fees
Stay at this luxury hotel in Prince Edward. Enjoy free Wi-Fi, free parking and free beach cabanas. Popular attractions Sandbanks Provincial Park and Prince Edward ...
Opens in a new windowDrake Devonshire and Motor Inn
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The Birch

The Birch

2 out of 5
137 Main St Prince Edward ON
The price is NZ$336 per night from 5 May to 6 May
NZ$336
5 May - 6 May
includes taxes & fees
Stay at this resort in Prince Edward. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Sandbanks Provincial Park and Prince Edward County Lavender ...
Opens in a new windowThe Birch
Don't see what you're looking for?
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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.