
Holiday rentals with a pool in Woolwich
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woolwich
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

HotTub & Cozy Fireplace - Headwaters Retreat
Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Rural Retreat, near to Elora
A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

Charming Hideaway: 1-bedroom Apartment
Whether you’re in town for sports, work, or family, you'll love how the apartment is: Fully Furnished: from kitchen to bedroom, we’ve got you covered. Cozy: Gas fireplace and a queen air mattress for extra guests. Private Entrance: Your own smart lock access. Outdoor Space: Your own private deck with a BBQ. Heated Pool: SHARED pool available mid May to September. Entertainment: Stay connected with WIFI and enjoy Netflix, Prime, and Disney on the Smart Parking: No worries about finding a spot

Alpaca farm stay and bunkie getaway.
A farm stay on your way to soaking up all that our county has to offer. The bunkie is located next to a restored century barn and an outdoor pool. The property is home to 5 alpacas, mini goats, chickens and our family dog. The bunkie is on a shared property with our home. It's 1 hour from Toronto, 20 minutes from Hamilton, 1-hour from Niagara-on-the-lake and 10 minutes from the historic Ancaster village. Antiquing, hiking, nature tours, golfing, wine tours, farmers markets and more close by.

Five Star Hayloft Suite
This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games
**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat
Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

LuxCondo in the downtown kitchener uptown waterloo
Modern and Sophisticated 1+1 apartment in the heart of Kitchener Downtown and Uptown Waterloo. It features modern furniture, a fully equipped kitchen, and a balcony with stunning sunset views. Enjoy exclusive amenities like a bowling alley, spa, pool table, and hydro swimming pool. The apartment comfortably sleeps 3 with two cozy beds. Located steps from top bars and restaurants, this apartment offers a blend of luxury and convenience. Perfect for business or leisure stays.

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.

The Captain's Cottage at Willow Pond
You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Chic Downtown Condo Retreat
This chic 1-bedroom condo is just steps away from KW's tech hub, the LRT station, City Hall, cafes, and the renowned Victoria Park, which hosts numerous festivals throughout the year. Boasting exceptional amenities like an exercise room, pool area, games room, and rooftop deck/garden, this upscale condo ensures an enjoyable stay. Experience downtown living at its finest! One parking spot is included, with paid parking available for additional vehicles.
Popular amenities for Woolwich rentals with a pool
House rentals with a pool

Modern Luxury House w/EV Charger & Heated Pool

Cottage Ambiance Private

Four seasons Pool Retreat near downtown!

The Bayfront Flat - Harbour Views + Private Pool!

Brant Paradise. Where luxury meets country charm.

Riverside Retreat /w Hot Tub & Sauna in Elora

Luxurious Home | Hot Tub & Pool | Sleeps 8

Under the Whispering Pines
Apartment rentals with a pool

Cozy Space

1BR+*TheKorner@Circa1877-One Bedroom+Suite

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

City Views & Private Balcony | Gym, Pool & More!

Stylish Downtown Suite with Patio & City Views

Bright & Modern Downtown Stay w/ Pool & Gym

Hamilton condo, 1 hour to Toronto or Niagara Falls

Highrise King Condo With Home Cinema -Free Parking
Other holiday rentals with a pool

Rustic Farmhouse w/ pool, tennis court on 100 Acre

Charming Studio Retreat • Heated Pool Available

KJ's Farmhouse w/SwimSpa Retreat

Milton Home- a Family Oasis

Country Villa Fergus Elora

Classy Basement - 2 Bedroom in Burlington

Luxury Farm w/ pool & hot tub. Weekend Getaway

High Rise 1 BR Condo w/Free Parking
When is the best time to visit Woolwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $93 SGD | $94 SGD | $94 SGD | $94 SGD | $93 SGD | $107 SGD | $111 SGD | $117 SGD | $108 SGD | $116 SGD | $97 SGD | $97 SGD |
| Avg. temp | -5°C | -5°C | 0°C | 7°C | 13°C | 19°C | 21°C | 20°C | 16°C | 10°C | 4°C | -2°C |
Quick stats about holiday rentals with a pool in Woolwich

Total holiday rentals
Explore 50 holiday rentals in Woolwich

Nightly prices starting at
Woolwich holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 1,710 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Woolwich holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woolwich rentals

4.8 Average rating
Woolwich stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with pools Region of Waterloo
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- Port Credit
- Victoria Park
- Glen Eden
- Royal Botanical Gardens
- Bayfront Park
- University of Waterloo
- Mount Chinguacousy
- Museum
- Wet'n'Wild Toronto
- Art Gallery of Hamilton
- Erin Mills Town Centre
- Conestoga College
- Dundurn Castle
- Caledon Ski Club LTD
- The Mississaugua Golf and Country Club
- Sheridan College - Trafalgar Road Campus
- St Jacob's Farmer's Market
- Conestoga College
- University of Guelph
- Elora Gorge
- Albion Falls
- Bingemans
- Cambridge Butterfly Conservatory
- Waterloo Park




