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Waupoos Vacation Rentals

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Our top choices for Waupoos vacation rentals

1. Cribs On The Hill

Cribs On The Hill
4.0 star property
Prince Edward
9.2 out of 10, Wonderful, (279 reviews)
"excellent location with ample parking."
Canada
Edward
The price is CA $170
CA $200 total
includes taxes & fees
Oct 12 - Oct 13
Cribs On The Hill

2. LAZY DAYZ Sunset Views and 2 minutes drive to Picton Main Street

LAZY DAYZ Sunset Views and 2 minutes drive to Picton Main Street
Prince Edward
10.0 out of 10, Exceptional, (46 reviews)
"Very clean, quiet and convenience, within 10 minutes drive to downtown, groceries and LCBO. Great vacation property"
Canada
Wai Hung Paul
The price is CA $140
CA $199 total
includes taxes & fees
Oct 13 - Oct 14
LAZY DAYZ Sunset Views and 2 minutes drive to Picton Main Street

3. Downtown Picton 2 Bedroom Boho Suite! (15 Minutes to Sandbanks)

Downtown Picton 2 Bedroom Boho Suite! (15 Minutes to Sandbanks)
Prince Edward
9.8 out of 10, Exceptional, (18 reviews)
"Great location, lovely space, Host was quick to reply to our questions. Would stay again :)"
Canada
Angele M.
The price is CA $290
CA $621 total
includes taxes & fees
Oct 12 - Oct 13
Downtown Picton 2 Bedroom Boho Suite! (15 Minutes to Sandbanks)

4. Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game

Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game
Prince Edward
9.6 out of 10, Exceptional, (23 reviews)
"Very clean, well equipped, attention paid to details. Would definitely come back"
United States
Harriett H.
The price is CA $160
CA $451 total
includes taxes & fees
Nov 9 - Nov 10
Gorgeous renovated-5 min to Main St-BBQ-Firepit-Free Sandbanks pass-Pac Man game

5. Steps to Lake on the Mountain, 10Minutes to Picton

Steps to Lake on the Mountain, 10Minutes to Picton
Prince Edward
6.0 out of 10, (2 reviews)
"The property is adequate. My primary grievance is the difficulty in corresponding with Ashley Cameron the owner of the property. She did not answer my request for how long it would take to receive back my security deposit (nor was said security deposit mentioned in 2 page contract) and it was only after I contacted VRBO that I got the money back minus the GST. The lack of response was frustrating and time consuming."
Canada
Dawn D.
The price is CA $226
CA $431 total
includes taxes & fees
Oct 12 - Oct 13
Steps to Lake on the Mountain, 10Minutes to Picton

6. Downtown Picton, 3 bedroom.

Downtown Picton, 3 bedroom.
Prince Edward
9.8 out of 10, Exceptional, (28 reviews)
"Great location, lovely home and very clean. We all loved it!"
Canada
Anthony
The price is CA $281
CA $698 total
includes taxes & fees
Oct 12 - Oct 13
Downtown Picton, 3 bedroom.

7. Central Picton Apartment, Sleeps 8; The Iron Horse

Central Picton Apartment, Sleeps 8; The Iron Horse
Prince Edward
9.8 out of 10, Exceptional, (6 reviews)
"Home was clean and easily fit 4 friends. Lots of parking and had necessary amenities! Good location for access to Picton and other towns in PEC."
United States
Deanna S.
The price is CA $302
CA $738 total
includes taxes & fees
Oct 12 - Oct 13
Central Picton Apartment, Sleeps 8; The Iron Horse

8. Relax in Style & Comfort in South Bay, PEC

Relax in Style & Comfort in South Bay, PEC
Prince Edward
8.6 out of 10, Excellent, (4 reviews)
"Clean, pet friendly, safe."
United States
Adam M.
The price is CA $496
CA $844 total
includes taxes & fees
Oct 10 - Oct 11
Relax in Style & Comfort in South Bay, PEC

9. The Birch

The Birch
3.0 star property
Prince Edward
9.6 out of 10, Exceptional, (71 reviews)
"Great little cabin!"
Canada
Boris
The price is CA $177
CA $258 total
includes taxes & fees
Nov 1 - Nov 2
The Birch

10. Central Picton, Games Room and steps from town!

Central Picton, Games Room and steps from town!
Prince Edward
9.4 out of 10, Exceptional, (10 reviews)
"Great location, excellent for our dog, perfect family retreat."
Canada
Sonya d.
The price is CA $328
CA $797 total
includes taxes & fees
Oct 11 - Oct 12
Central Picton, Games Room and steps from town!

11. Downtown Picton 2 Bedroom Professionally Designed Suite

Downtown Picton 2 Bedroom Professionally Designed Suite
Prince Edward
9.6 out of 10, Exceptional, (12 reviews)
"Our stay here was easy and very comfortable. Beautiful place."
United States
Jordana P.
The price is CA $213
CA $521 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Picton 2 Bedroom Professionally Designed Suite

12. Clarke Road Retreat

Clarke Road Retreat
Prince Edward
10.0 out of 10, Exceptional, (14 reviews)
Clarke Road Retreat

13. Downtown Picton Retreat |Near Sandbanks & Wineries

Downtown Picton Retreat |Near Sandbanks & Wineries
Prince Edward
10.0 out of 10, Exceptional, (18 reviews)
"We very much enjoyed our visit. The house was clean, comfortable and very well equipped. Easy walk to downtown."
United States
Jim S.
The price is CA $222
CA $457 total
includes taxes & fees
Nov 5 - Nov 6
Downtown Picton Retreat |Near Sandbanks & Wineries

14. NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)

NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)
Prince Edward
9.8 out of 10, Exceptional, (15 reviews)
"We had a lovely, lovely week!! The house is spacious, comfortable, and well appointed. We enjoyed the BBQ and outdoor space in particular. It is also near lots of good trails for running and close to Main Street. "
Canada
Catherine S.
The price is CA $463
CA $1,000 total
includes taxes & fees
Oct 12 - Oct 13
NEW Professionally Designed 8 Bed Home (w. 2 Sandbanks Passes)

15. Feel the Country Vibe in this 4-bedroom Farmhouse Inn! Close to Kingston, PEC

Feel the Country Vibe in this 4-bedroom Farmhouse Inn! Close to Kingston, PEC
Greater Napanee
8.4 out of 10, Very good, (13 reviews)
The price is CA $231
CA $441 total
includes taxes & fees
Oct 12 - Oct 13
Feel the Country Vibe in this 4-bedroom Farmhouse Inn! Close to Kingston, PEC

16. Fantastic Tiny House with Barbecue and Fire Pit in Deseronto, Ontairo

Fantastic Tiny House with Barbecue and Fire Pit in Deseronto, Ontairo
deseronto
Fantastic Tiny House with Barbecue and Fire Pit in Deseronto, Ontairo

17. 1971 Vintage Modern Airstream w/ Cowboy Tub near PEC

1971 Vintage Modern Airstream w/ Cowboy Tub near PEC
Hastings County
9.4 out of 10, Exceptional, (3 reviews)
"We really enjoyed our three nights of glamping! We had our meals on the deck and enjoyed the outdoor fireplace. We spent one day on the beach at Sandbanks (35 minutes) and one day exploring Prince Edward County with winery visits and lunch at a micro-brewery. The Airstream is well equipped. The coffee maker is a French press, so you don't need filters; there is a cannister of coffee, sugar, and coffee creamer. The campground is quiet -- we slept with windows open."
Canada
Bruce B.
1971 Vintage Modern Airstream w/ Cowboy Tub near PEC

18. 1971 Vintage Modern Airstream with Cowboy Tub

1971 Vintage Modern Airstream with Cowboy Tub
deseronto
1971 Vintage Modern Airstream with Cowboy Tub

19. Incredible Tiny House with Fireplace, Fire Pit and Pizza Oven in Deseronto, Ontario

Incredible Tiny House with Fireplace, Fire Pit and Pizza Oven in Deseronto, Ontario
deseronto
Incredible Tiny House with Fireplace, Fire Pit and Pizza Oven in Deseronto, Ontario

20. Tiny Home Near Wine Country with Stargazing Loft

Tiny Home Near Wine Country with Stargazing Loft
Hastings County
10.0 out of 10, Exceptional, (2 reviews)
"Our host was fabulous, all the little extras made our stay so enjoyable. "
Canada
Laurie
Tiny Home Near Wine Country with Stargazing Loft
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waupoos Hotel Reviews

Find out more about Waupoos

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Waupoos. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Waupoos?

Yes, there are vacation rentals close to the most popular local attractions in Waupoos, or you can select a secluded option if you're looking for a relaxing stay. Waupoos is known for its wineries and museums.

What are some of the best vacation home rentals in Waupoos?

The Birch: This vacation home rental outside of Waupoos offers a private yard, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a microwave and kitchenware can make your vacation run smoothly.

How many vacation rentals are there in Waupoos?

Choose from 7 Expedia vacation rentals in Waupoos for a memorable vacation.

What can I see and do in Waupoos?

Cultural attractions include Rose House Museum, whereas Lake Ontario is a spot to enjoy nature. While here, County Cider Company and Waupoos Winery are other places worth a visit.

What are vacation rentals like in Waupoos?

Vacation rentals are private accommodations you can stay in for several days or longer in Waupoos. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.