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!

Mar 22 – 29

G$28,266 GYD per night

Guest favorite

Home in Prince Edward

4.92 out of 5 average rating, 130 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.

Oct 24 – 31

G$34,236 GYD per night

Guest favorite

Apartment 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.

Dec 15 – 22

G$24,208 GYD per night

Guest favorite

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.

Sep 26 – Oct 3

G$85,846 GYD per night

Guest favorite

Guest suite in Prince Edward

4.99 out of 5 average rating, 292 reviews

Rockery Suite - Picton 4 min to Main St ParkPass

Our spacious & welcoming Rockery Suite (licensed) - an inviting, fully equipped apartment with private entrance. Located less than 5 minutes from downtown Picton, the harbour, fine & casual dining, cafes, pubs, breweries, galleries & studios, shopping & so much more. Or take a short scenic drive to local wineries, beaches, ski & walking trails, Sandbanks Park, Lake On The Mountain, Glenora Ferry, Bloomfield, Wellington. Endless year round possibilities. Come and explore Prince Edward County.

Jan 2 – 9

G$18,933 GYD per night

Guest favorite

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.

Nov 14 – 21

G$20,353 GYD per night

Guest favorite

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

Jan 29 – Feb 5

G$22,569 GYD 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!

Nov 13 – 20

G$22,214 GYD 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.

May 16 – 23

G$38,346 GYD per night

Guest favorite

Apartment in Prince Edward

5.0 out of 5 average rating, 148 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 29 – Jan 5

G$19,396 GYD per night

Guest favorite

Home in Prince Edward

4.94 out of 5 average rating, 176 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

Jun 6 – 13

G$34,268 GYD per night

Guest favorite

Apartment in Prince Edward

4.99 out of 5 average rating, 235 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.

Dec 11 – 18

G$52,235 GYD per night