Holiday rentals in Wellington

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Top-rated holiday rentals in Wellington

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest house in Prince Edward

4.95 out of 5 average rating, 201 reviews

"On the Syde" - GUEST HOUSE

Romantic get-a-way for two! Cozy and sweet, just what the doctor ordered. If you are looking for private, NOT shared space, this little "On The Syde" guest house might be for you. Included is a kitchenette, continental BF, coffee, TV, WI-FI 6E, fresh sheets, towels, and quiet at night! Check out the chic Town of Wellington in beautiful Prince Edward County! If you want wineries, nightlife, good restaurants and a beach they are all just a few minutes away! Book now, singles welcome too!

1–8 Mar

$179 SGD per night
Guest favourite

Home in Prince Edward

4.97 out of 5 average rating, 115 reviews

Prince Edward Landing

Victorian Home in PEC gets a full renovation to become a one of a kind vacation home. Featured in the Globe & Mail the house is a 2018 restoration of old-world charms with as many contemporary comforts as one wishes. From the gorgeous landscape and a screened-in, white-trim front porch to the fully modern spectacular interior The back of the house is a stunning starkly contemporary black box, designed by architect Jay Pooley, a lecturer at the University of Toronto’s school of architecture.

9–16 May

$512 SGD per night
Guest favourite

Home in Hillier

4.94 out of 5 average rating, 236 reviews

Cozy Postmaster’s House - Beach/Park Pass Included

Weekly SUMMER bookings now open, Saturday to Saturday only, beach/park car pass included! Escape to the birthplace of wine in Prince Edward County at the historic Postmaster's House in Hillier. This charming 3-bedroom house from the 1890s offers a cozy fireplace and is surrounded by over 40 vineyards. Explore wineries, restaurants, breweries, North Beach, Millennium Trail, and Wellington village, all just a bike ride away. Unwind and immerse yourself in the beauty of this idyllic destination.

23–30 Apr

$177 SGD per night

Popular amenities for Wellington holiday rentals

Stay near Wellington's top sights

Drake Devonshire240 locals recommend
Wellington Beach69 locals recommend
The Lakeside Motel34 locals recommend
La Condesa109 locals recommend
Midtown Brewing Company170 locals recommend
East and Main Bistro126 locals recommend

Other great holiday rentals in Wellington

Guest favourite

Home in Prince Edward

5.0 out of 5 average rating, 121 reviews

The Hull House - Lake Ontario Waterfront w Sauna

11–18 Sep

$960 SGD per night
Guest favourite

Guest suite in Prince Edward

4.9 out of 5 average rating, 142 reviews

Room by the Vineyard 1

26 Jan – 2 Feb

$151 SGD per night
Guest favourite

Home in Prince Edward

4.94 out of 5 average rating, 175 reviews

Globe House Prince Edward County

13–20 Aug

$223 SGD per night
Guest favourite

Home in Prince Edward

4.92 out of 5 average rating, 126 reviews

Prince Edward County - The Annex - Family Friendly

29 Dec – 5 Jan

$223 SGD per night
Guest favourite

Bungalow in Prince Edward

4.97 out of 5 average rating, 173 reviews

Fitzroy Fieldhouse - Near Wineries With Free Bikes

17–24 Oct

$349 SGD per night
Guest favourite

Guest suite in Prince Edward

4.99 out of 5 average rating, 289 reviews

Rockery Suite - Picton 4 min to Main St ParkPass

27 Aug – 3 Sep

$190 SGD per night
Guest favourite

Home in Wellington

4.98 out of 5 average rating, 192 reviews

The Red Brick House - Wellington

15–22 Nov

$509 SGD per night
Guest favourite

Bungalow in Prince Edward

4.91 out of 5 average rating, 315 reviews

Bright & Cozy Bungalow Close to Downtown Picton

25 Aug – 1 Sep

$214 SGD per night
Guest favourite

Guest suite in Prince Edward

5.0 out of 5 average rating, 44 reviews

Wellington Guest Suite on Main!

25 Dec – 1 Jan

$232 SGD per night
Guest favourite

Home in Prince Edward

5.0 out of 5 average rating, 20 reviews

The Trimble Lake House, Ontario

11–18 Nov

$569 SGD per night
Guest favourite

Flat in Prince Edward

4.94 out of 5 average rating, 52 reviews

Gorgeous & Spacious 3 Bdrm Suite

1–8 Nov

$225 SGD per night
Guest favourite

Villa in Prince Edward

4.98 out of 5 average rating, 44 reviews

The Getaway Wellington PEC Suite #1

28 May – 4 Jun

$213 SGD per night

Quick stats about holiday rentals in Wellington

Total rentals

140 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

9.4K reviews

Nightly prices starting at

$108 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Prince Edward County
  5. Prince Edward
  6. Wellington