Vacation rentals with a pool in Woolwich

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Top-rated rentals with a pool in Woolwich

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Waterloo

4.93 out of 5 average rating, 28 reviews

Entire Guest Unit+Free Parking by Glenbridge Plaza

Located in a prime location in Waterloo, one of the most desirable safe and quiet neighborhoods of Lincoln Heights, this unique place perfectly blends privacy and comfort. Just minutes away from University of Waterloo, Wilfrid Laurier University, Conestoga College, highways (7/8),2 minute walk to Glenbridge Plaza, Zehrs Market (Grocery), CIBC Bank, A&W, Canadian Pizza, pharmacies, etc. It is an 8-minute drive to the St. Jacobs Farmers Market and only a 5-minute drive fromWalmart.Busstop is here

May 15 – 22

G$21,263 GYD per night

Guest favorite

Camper/RV in Saint Agatha

5.0 out of 5 average rating, 37 reviews

Modern Retreat Destination Trailer

Experience glamping in our modern destination trailer nestled in the country side of St. Agatha, minutes away from Waterloo. If you aren't up to the hassle of camping but want to experience nature in stylish comfort, this is the perfect place for you. Enjoy sitting on the spacious deck, roasting marshmallows by the fire, and star gazing above. Experience the peaceful walking trails in the woods and lounging by the large unheated swimming pool (seasonal from June to September, weather permitting)

May 6 – 13

G$28,030 GYD per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private HotTub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

G$15,654 GYD per night

Guest favorite

Condo in Waterloo

4.89 out of 5 average rating, 46 reviews

Cozy 1BR Condo w/ Insuite LDRY, Gym & Free Parking

Indulge in the comforts of home away from home with our fully equipped kitchen, complete with modern appliances and ample counter space. Our in-suite laundry is at your disposal, so you can pack light. Step out onto our private balcony and take in the breathtaking views of the city, while enjoying a cup of coffee. Stay connected with high-speed internet and unwind with your favourite shows on our smart TV, making your stay more enjoyable, so you can relax and recharge in style.

Feb 18 – 25

G$17,950 GYD per night

Guest favorite

Home in Cambridge

4.91 out of 5 average rating, 240 reviews

Spacious Bungalow Guest House

Welcome to our stylish, modern, guest house nestled in a private country setting. Enjoy all of the updated conveniences while experiencing rustic surroundings. Peaceful and stress free for the whole family. Located minutes to the City of Cambridge. Note: The pool is outdoor and is generally open by Victoria Day weekend (3rd weekend in May) until Labour Day weekend (last weekend in August), but if it is warm earlier or later we may extend that by a few weeks. Please inquire.

Dec 26 – Jan 2

G$34,022 GYD per night

Superhost

Apartment in Kitchener

5.0 out of 5 average rating, 4 reviews

The hideaway

It’s a unique space , perfect to work anywhere in tri-cities close to st jacobs and Elora also. The lower floor is cozy. It’s has its own entrance .If longer stays the area it will be cleaned once a week a no extra charge. It’s not a hotel room , it’s better , feels like home. Lots of character. Covered patios to bbq. ID required with photo Perfect to visit the area and enjoy the grand river. we only use thieves natural cleaning products,and no scents on sheets,towels.

Nov 30 – Dec 7

G$15,815 GYD per night

Guest favorite

Apartment in Ariss

4.97 out of 5 average rating, 111 reviews

Rural Retreat, 1 bedroom suite near Elora

The perfect winter country retreat in Ariss. Relax in the hot tub and watch the birds. Well situated between Elora, Fergus, St Jacobs and Guelph. Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking, biking, snowshoeing, snowmobile trails & Chicopee Ski Resort. King bed, portable crib, shower, kitchenette, seating area, natural light. Swimming pool, hot tub, large backyard, bonfires, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

Sep 2 – 9

G$26,811 GYD per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Mar 4 – 11

G$34,935 GYD per night

Guest favorite

Home in Centre Wellington

5.0 out of 5 average rating, 7 reviews

A Quiet Oasis in Elora

Relax with the whole family at this peaceful place to stay. Wonderfully landscaped yard, cozy up in the front garden and enjoy this quiet street. Stay and play in the backyard, with lawnspace for games, a pool and an outdoor dining area with gas BBQ and bar. The inside offers a open concept main living with full kitchen, a chefs gas range and large fridge. Find all the things you need to make the perfect meal. The basement offers a quiet retreat, or game's area.

Jul 19 – 26

G$43,025 GYD per night

Guest favorite

Home in Waterloo

4.94 out of 5 average rating, 123 reviews

EXECUTIVE HOME WITH POOL IN WATERLOO

Welcome to Waterloo!! This beautiful executive house is located in Waterloo. High-end finishes include custom kitchen, granite countertops, and stainless steel appliances. Short distance to universities and colleges. Easy access to the highway. ***POOL IS NOT HEATED**** **PLEASE NOTE THE POOL WILL BE AVAILABLE ONLY IN SUMMER BETWEEN MAY LONG WEEKEND AND Sept 15** ★★★★★SUPERHOST★★★★★ ✪ Upgraded High Speed Internet ✪ Parking provided! ✪ Washer/Dryer

Aug 4 – 11

G$114,699 GYD per night

Guest favorite

Guest suite in Stratford

4.97 out of 5 average rating, 167 reviews

Private airy space in a perfect location

With a walkable score of 86, our private room in a friendly neighbourhood is ideal for your visit to Stratford. This space has hard wood floors, high ceilings, ceiling fan and heating/central air conditioning. A cozy electric fireplace to relax in winter. Our central location is just minutes away from all 3 theaters, as well as the Avon River, various parks, the tennis club, and all that downtown has to offer. A private parking space is included.

Nov 24 – Dec 1

G$21,277 GYD per night

Guest favorite

Guest suite in Newton

4.89 out of 5 average rating, 186 reviews

Century Home Apartment next to the G2G Trail

This rural property is a great place to relax and unwind in the heart of Amish and Mennonite country. The location is perfect for outdoor enthusiasts with the G2G hiking/biking trail literally being in the backyard. The second storey Apartment has lots of charm and character. There is ample parking, reliable wifi, outdoor hot tub, pool and a patio with firepit. The famous Anna Mae's Restaurant and the Zehr's Country Market are 1 km down the road.

Dec 5 – 12

G$14,959 GYD per night