House holiday rentals in Wellington

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Top-rated house rentals in Wellington

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Guest favourite
The exterior of the cottage showcases blue siding and features a welcoming porch with bright yellow chairs. A black door with decorative glass invites guests into the home. The design reflects a blend of cottage charm and modern touches.
Home in Wellington
4.98 out of 5 average rating, 218 reviews

Little Blue Cottage: Perfect for families!

This little blue house is in the heart of Wellington. 5 min to The Drake, grocery, cafes, shops & market. Easy walk to the beach and trail for miles of biking, even past wineries! Newly renovated with a lovely kitchen & bathroom. This house has 2 bedrooms, (1 queen bed and 2twin beds). The home is sunny and has been designed with comfort in mind. Privacy & location make this a great base to explore PEC! Please note that July & August bookings are minimum 7 days with check in/out on Saturday

Top guest favourite
An aerial view captures a spacious backyard featuring a modern heated pool surrounded by lounge chairs. A fire pit seating area is placed nearby, with the backdrop of trees and a vibrant sunset sky illuminating the scene. The contemporary back of the house faces the pool.
Home in Wellington
4.97 out of 5 average rating, 164 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.

Top guest favourite
A spacious living area is furnished with soft sofas adorned with decorative pillows. Two wicker chairs provide additional seating. A round coffee table sits at the center on a natural fiber rug, creating a comfortable gathering space. Natural light filters through nearby openings.
Home in Wellington
5 out of 5 average rating, 251 reviews

Wellington Summer Home | King Suite (5 BDR•3 Bath)

10 Guests Max (children included) STA LICENCE NO. ST-2019-0255 Welcome to The Twelve PEC! Our home is your tranquil getaway located in the heart of Prince Edward County on a quiet family friendly cul-de-sac in the small lakeside town of Wellington. Occupancy is firm at 10 persons total (infants and children included)• No exceptions (per licensing & fire code compliance) Not suitable for parties or boisterous groups. Kindly review all rules and listing prior to sending a booking request.

Top guest favourite
A charming exterior of The Coach House is depicted, featuring a unique multicolored wooden façade. The structure is framed by lush greenery, and a wooden planter with a variety of plants is positioned at the front, adding to the inviting atmosphere of the property.
Home in Picton
4.88 out of 5 average rating, 490 reviews

The Coach House - Summer Sandbanks Pass Included

The Coach House is a cozy self-contained suite with a private entrance, backyard and parking. Located in Picton this unique space is a short walk to the harbor and Main Street’s restaurants and shopping. The home is also a short drive to Base 31, Lake on the Mountain, Sandbanks Provincial Park, local wineries, hiking trails and art galleries. The Coach House is perfect for couple or small family. The home has air conditioning for the warm summer nights! License No. ST-2019-0306

Guest favourite
The entrance of Dragonfield House is presented with a modern metal exterior, framed by winter frost and snow. Large windows allow natural light to fill the space, while the landscape features frosted grass and trees, creating a serene winter atmosphere.
Home in Prince Edward
4.94 out of 5 average rating, 201 reviews

Dragonfield House: a beautiful stay in central PEC

Dragonfield House: STA License No. ST-2024-0206 Featured in Canadian House and Home, March 2015, Dragonfield House was designed with a contemporary approach to country living. It is a four bedroom split-level country house, plus a guest yoga retreat with all the amenities of a city home. It features a heated salt-water pool (Mid May until Mid October) and a brand new year round hot tub for six people! There are three work/desk areas within the house ideal for remote working.

Top guest favourite
The Hull House sits gracefully on a limestone shelf overlooking Lake Ontario. Lush greenery surrounds the home, complemented by a spacious lawn. A sunken deck with seating faces the water, providing an inviting outdoor space for relaxation. Grapevines can be seen in the distance.
Home in Prince Edward
4.98 out of 5 average rating, 223 reviews

The Hull House - Lake Ontario Waterfront w Sauna

Perched atop a picturesque limestone shelf on the shores of Lake Ontario, just 4 kilometres west of Wellington, is the Hull House. A thoughtfully curated County Lakehouse that boasts an infinite view of blue waters and ever changing skies. Ideally located at the centre of Prince Edward County’s web of vibrant restaurants and wineries, the Hull House offers 200 + feet of private lake frontage, 2 acres of land, a sauna and many luxuries for your well deserved vacation.

Top guest favourite
A classic two-story red brick home is framed by a well-kept lawn, featuring blooming flower beds and mature trees. The entrance is highlighted by a symmetrical façade with large windows, inviting natural light. A paved path leads to the front door, enhancing the welcoming appearance.
Home in Wellington
4.98 out of 5 average rating, 235 reviews

The Red Brick House - Wellington

An original, circa 1860s county home, The Red Brick House combines old world heritage with contemporary design. The bright, welcoming space, sleeps up to six, and is in a prime location just steps away from both Wellington Beach and the Drake Devonshire. While you’re here you can hop on a bike at the rental shop across the street, go explore the beautiful wineries, restaurants, shops, and more. The central location means that you’re close to it all.

Top guest favourite
The lakeside retreat is showcased, featuring a two-story structure with a spacious upper deck and large glass doors. Lush greenery lines the property, while a wooden dock extends towards the water. The inviting facade is complemented by a gabled roof and a chimney.
Home in Wellington
4.98 out of 5 average rating, 253 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.

Guest favourite
A warm living area features a towering Christmas tree adorned with twinkling lights, standing in front of a glass-paned door. Comfortable seating arrangements include a plush sofa and armchairs, with a cozy rug placed on polished wooden floors.
Home in Wellington
4.88 out of 5 average rating, 232 reviews

The Log House - Wellington - with Fast Wifi

Welcome to your beautiful Log House right in the town of Wellington! A 10 minute walk from the Drake Devonshire and all the restaurants, shops and galleries of Main Street. This spacious 3000 sq. ft. log home has 5 inviting bedrooms, 2 bathrooms and a large chef’s kitchen. It is perfectly situated for exploring the best wineries in Prince Edward County, most are within a 5-10 min drive. License Number: ST-2020-0086 R1

Top guest favourite
The exterior of the guest house showcases a modern wooden facade, accented by large windows. Soft outdoor lighting highlights the space, and a white bench is situated near a garden of wildflowers, creating a calm, inviting environment.
Home in Consecon
4.95 out of 5 average rating, 367 reviews

Hygge House, Cozy Boutique Guest House

Maximum 2 adults and up to 2 children (aged 9 and under). Inspired by the Danish word "Hygge", this little guest house is cozy, modern, and has everything you need for a quiet and peaceful getaway in the County. Nestled in rural Consecon, you'll get to unwind and recharge, all the while being just minutes away from grabbing a coffee, heading to the beach, or winery hopping in Hillier. Licence number ST-2019-0349 R2

Guest favourite
A modern house is set against a sunset sky, surrounded by tall grass and scattered trees. The exterior, featuring large windows, reflects the colors of dusk, creating a harmonious blend with the natural landscape.
Home in Prince Edward
4.95 out of 5 average rating, 222 reviews

Globe House Prince Edward County

STA License ST-2019-0027 Ease yourself into modern luxury, a perfect base for your romantic getaway in The County. Cozy up. Here you'll hear the sound of crickets, not sirens; smell flowers, not fumes; see stars, not headlights. There's an online article about the Globe House in the Globe and Mail which I can't link to here but you can find it if you search for: globe and mail prince edward county building a house

Top guest favourite
A two-story house is seen from the street, featuring a gabled roof and light-colored siding. The front porch has a decorative railing and a round window above the entrance. Surrounding greenery complements the neighborhood setting, with utility wires visible overhead.
Home in Picton
4.93 out of 5 average rating, 646 reviews

No Fees, Walk to Bars, restaurant. drive Beach

No Fees - House Downtown Picton, Ontario, only 10 Minutes to Beach & after day at Beach, come back to house, freshen up & never need to get back in car-steps away to Pubs, Breweries, bike trails, theatre, Groceries & LCBO - IMPORTANT: All weekends minimum 2 nights (Fri & Sat). Rates are based on 2 people & additional charges per person, per night where more than 2 guests. No animals due to allergies. Free Parking

Popular amenities for house rentals in Wellington

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Avg. price$240 SGD$229 SGD$240 SGD$293 SGD$343 SGD$381 SGD$414 SGD$417 SGD$330 SGD$290 SGD$259 SGD$225 SGD
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Quick stats about house rentals in Wellington

  • Total holiday rentals

    Explore 60 holiday rentals in Wellington

  • Nightly prices starting at

    Wellington holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Wellington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellington rentals

  • 4.9 Average rating

    Wellington stays are highly rated by guests – averaging 4.9 out of 5!

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