Vacation rentals in Wellington

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Top-rated vacation rentals in Wellington

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Guest favorite

Guesthouse 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!

Apr 20 – 27

ﺩ.ﺇ490 per night

Guest favorite

Home in Prince Edward

4.97 out of 5 average rating, 116 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.

Oct 14 – 21

ﺩ.ﺇ1,380 per night

Guest favorite

Bungalow in Prince Edward

4.91 out of 5 average rating, 327 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.

Oct 31 – Nov 7

ﺩ.ﺇ369 per night

Guest favorite

Guest suite in picton

4.96 out of 5 average rating, 423 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

Apr 23 – 30

ﺩ.ﺇ427 per night

Guest favorite

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!

Feb 28 – Mar 7

ﺩ.ﺇ396 per night

Guest favorite

Guesthouse in Wellington, Prince Edward County, ON

4.97 out of 5 average rating, 225 reviews

Beachside Suite in Wellington Prince Edward County

Beachside Suite in Wellington is a renovated open concept loft on the 2nd floor of our 1870’s barn. Parking included. The location is outstanding; a 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, has a 3 piece ensuite, large kitchenette, private deck with BBQ, gorgeous views and is in the heart of wine Country. See also our Wellyside Suite on Airbnb. Licence ST-2019-0352 R2.

Jul 26 – Aug 2

ﺩ.ﺇ936 per night

Guest favorite

Apartment in Prince Edward

4.89 out of 5 average rating, 100 reviews

Modern open concept farmhouse studio w/parking

Welcome to Unit #3 at the Picton Commons! Located on Main St. near historic Picton Harbour, this mid-century modern studio offers a stylish and cozy retreat for those looking to explore PEC. Our unit features a tastefully renovated interior, complete with a king sized bed, farmhouse kitchen with new appliances, an adorable reading nook and free street parking directly outside. Steps away from the county fairground and a short walk to the best restaurants and shops Picton has to offer.

Nov 29 – Dec 6

ﺩ.ﺇ456 per night

Guest favorite

Apartment in Prince Edward

5.0 out of 5 average rating, 152 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!

Dec 21 – 28

ﺩ.ﺇ341 per night

Guest favorite

Apartment in Prince Edward

4.92 out of 5 average rating, 236 reviews

THE Village Suites - THE LOFT

Beautiful 1 bedroom suite on Main Street, in the Heart of Wellington. Steps away The Drake Devonshire and East and Main Bistro. For great coffee and breakfast head next door to Piccolina 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.

Nov 22 – 29

ﺩ.ﺇ426 per night

Guest favorite

Apartment in Prince Edward

4.94 out of 5 average rating, 105 reviews

Central Location in Picton, 2 Bed, Dog Friendly

We invite you to stay in our beautiful two-bedroom suite located in the heart of Prince Edward County. A one-minute walk to Main Street in Picton and a 15-minute drive to Sandbanks Provincial Park. This space has a fully stocked kitchen, bathroom, dining room, living room and laundry. Enjoy a walk to the Picton Harbour, go for a picnic at the gorgeous Macaulay Heritage Park, or dinner at one of the nearby restaurants in Picton.

May 10 – 17

ﺩ.ﺇ370 per night

Guest favorite

Home in Prince Edward county

4.99 out of 5 average rating, 200 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.

Nov 20 – 27

ﺩ.ﺇ2,044 per night

Guest favorite

Apartment in Prince Edward

4.99 out of 5 average rating, 236 reviews

Bark Guesthouse in Prince Edward County

Bark Guesthouse (Licence # ST-2020-0243) is a newly built guesthouse in Prince Edward County, set on a 2-acre property surrounded by vineyards. Within walking or biking distance of 20 plus wineries, lavender farm and a short drive to the villages of Wellington, Bloomfield and Picton. If you are looking to escape the city and enjoy a slower pace of life, then Bark Guesthouse might just be the place for you.

Jan 12 – 19

ﺩ.ﺇ919 per night