Kid-friendly holiday rentals in Wellington

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Wellington

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Prince Edward

4.95 out of 5 average rating, 203 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!

23–30 Jun

$184 SGD per night

Guest favourite

Home in Prince Edward

4.92 out of 5 average rating, 131 reviews

Prince Edward County - The Annex - Family Friendly

Inviting, highly rated 2-storey, guest suite. Bright and clean. Two queen beds & two twins. Large backyard to enjoy the stars around a campfire. Head to Sandbanks Park. Swim, discover walking trails and sand dunes. Visit local wineries, restaurants and craft breweries along with quaint boutique shops. In the cooler months, plan to soak in the hot tub or sip a drink on the patio around a propane fireplace. Blankets, robes, slippers provided. Available Oct - end of May. Parking included.

8–15 Feb

$224 SGD per night

Guest favourite

Flat in Prince Edward

4.94 out of 5 average rating, 388 reviews

The Village Suites - THE VINEYARD

Beautiful 1 bedroom suite on Main Street, in the Heart of Wellington. Steps away The Drake Devonshire, East and Main Bistro and Midtown Brewery Across the street enjoy our local piano bar "The Stache". For great coffee and breakfast head to Enid Grace Cafe. Also, Ice cream and bike rentals just outside your door Head out for the afternoon to enjoy over 40 Wineries surrounding Wellington such as Hillier Estates , Sandbanks, Casa-Dea plus many more! A must see is our World famous Sandbanks Beach.

3–10 Dec

$159 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.

24 Sep – 1 Oct

$611 SGD per night

Guest favourite

Bungalow in Prince Edward

4.91 out of 5 average rating, 323 reviews

Bright & Cozy Bungalow Close to Downtown Picton

This bright & cozy cottage-style bungalow is the perfect home base for your PEC getaway! It is centrally located in the heart of Picton, offering 1 bedroom, 1 bath, office area, deck with BBQ & small yard. Comfortably accommodates two adults. Short 5 min walk to downtown, where you can enjoy The Royal Hotel, boutiques, restaurants, cafe's, galleries & more. A short drive to Sandbanks, wineries and breweries. Includes high speed Wi-Fi, central AC/heat, parking & annual Sandbanks day-use pass.

14–21 Nov

$133 SGD per night

Guest favourite

Guest suite in picton

4.96 out of 5 average rating, 420 reviews

Westlake’s Suite 25

A beautiful self contained Suite within our home with self check in. A sitting room with kitchenette, leading into a separate spacious bedroom with ensuite. The large windows allow for an abundance of natural light throughout. Relax and reflect on the front porch. Located in the heart of the county, Westlake, which is approx. 15 minutes from downtown Picton. Walking distance to the Dunes beach at Sandbanks Provincial Park. Parking spot and Sandbank’s Pass included. Occupancy 2 adults

22 Feb – 1 Mar

$148 SGD per night

Guest favourite

Guest suite in Prince Edward

4.91 out of 5 average rating, 337 reviews

Walk to Drake, 20+ Hillier wineries, Rotary Beach!

Welcome to Prince Edward County! Our spacious 800sqft rental has you located within a 5 minute walk to downtown Wellington where you can enjoy amazing meals at the Drake Devonshire, Idle Wild, East & Main and El Condesa. You're a 20 minute bike ride from renowned wineries such as Norman Hardie, The Grange, Closson Chase and 20+ others. Finally, you're only a 20 minute drive from Sandbanks, an Ontario provincial park with three expansive sandy beaches on Lake Ontario. Enjoy County living!

26 Sep – 3 Oct

$141 SGD per night

Guest favourite

Loft in Wellington, Prince Edward County, ON

4.98 out of 5 average rating, 229 reviews

Wellyside Suite in Wellington Prince Edward County

Wellyside Suite in Wellington is a renovated open concept loft on the 2nd floor of our 1870’s home. The location is outstanding; 30 second walk to the beach and a 5 minute walk to fabulous places like the Drake Devonshire and more. Perfect for couples; it's private, air conditioned, 4 piece ensuite with in-floor heating, kitchenette, private deck (BBQ) with gorgeous views in the heart of wine country. Includes parking Also see Beachside Suite on Airbnb. Licence ST-2019-0352 R2.

7–14 Nov

$203 SGD per night

Guest favourite

Cottage in Prince Edward

4.99 out of 5 average rating, 106 reviews

Picton Bay Hideaway

Picton Bay Hideaway is a family owned and operated licensed waterfront bungalow with 2 bedrooms and a walk out basement that can comfortably sleep up to 4 adults plus 2 children. This getaway is ideal for those wanting to slow down, relax and spend quality time with loved ones or for those who are looking for a quiet and peaceful workspace retreat. Whether you are a wine, food, fishing, or a beach goer, there is something for everyone in Prince Edward County (PEC)!

1–8 Mar

$211 SGD per night

Guest favourite

Flat in Prince Edward

5.0 out of 5 average rating, 149 reviews

Speakeasy Suites Picton, Prince Edward County

Whether you’re looking for a quiet, cozy, and comfortable stay, or if you’re an avid Instagrammer searching for a modern vacation experience, this luxury two-bedroom, fully-loaded suite in central Prince Edward County is the stay for you. Steps away from Tim Hortons, 555 Craft Brewery, The County Canteen, and many other popular local spots, you’re not far away from the experience that has made Prince Edward County the go-to tourist spot in Ontario!

25 Mar – 1 Apr

$127 SGD per night

Guest favourite

Home in Prince Edward county

4.98 out of 5 average rating, 199 reviews

The West Lake House

This luxurious 5 bedroom lakeside retreat is the perfect spot for family and friends to enjoy all that Wellington has to offer. This home on main street is only a short walk to shops and restaurants in downtown Wellington. We are a twenty minute drive from the sandbanks provincial park and provide two vehicle passes for quick access through your stay. You can also drive or cycle to the 26 wineries in our immediate area.

2–9 Jan

$867 SGD per night

Guest favourite

Guest house in Wellington, Prince Edward County

4.93 out of 5 average rating, 120 reviews

Welcome to our lovely Wellington cottage!

Our beautiful cottage is the perfect place for a getaway! Lake Ontario is literally around the corner, it's a 5 minute walk to fabulous Wellington restaurants and The Millennium Trail, and very close to some of the best wineries in the county. EV charger on-site. Sorry but our cottage is not suitable for pets, infants or children. License ST-2019-0265. Maximum 2 guests/1 car.

14–21 Sep

$225 SGD per night