Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Downtown Toronto

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Top guest favourite

Home in The Beaches

4.99 out of 5 average rating, 143 reviews

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Guest favourite

Guest suite in Uxbridge

4.78 out of 5 average rating, 9 reviews

Hilltop Getaway|Scenic Views |Back to ForestTrails

Escape to this stunning hilltop 2-bedroom Airbnb, nestled on 22 acres of beautiful woodland just 2 minutes from Lake Ridge Ski Resort.Enjoy breathtaking panoramic views of the mountains from your private retreat, perfect for those seeking both relaxation and adventure This cozy unit is ideal for hikers, with direct access to Glen Major Forest and scenic trails right at your doorstep There is no living room, you will have 2 bed rms, 1 washroom and a kitchen This unit is a portion of main cottage

Guest favourite

Home in Burt

4.92 out of 5 average rating, 200 reviews

Laketown Cottage:House with large yard by the lake

You’ll love our beautiful newly renovated cottage by the lake!! Outside you'll enjoy a really large yard: great to play lawn games, lay in the hammock or recline under the covered porch with a great book! Inside you'll enjoy a spacious living room where you can curl up by the electric fireplace or enjoy a movie together. Full kitchen & separate dining room make sharing meals or playing games indoors easy. For family vacation, personal retreat, or a fishing excursion, this is the perfect spot!!

Top guest favourite

Guest suite in Burlington

4.94 out of 5 average rating, 132 reviews

Burlington core close to lakefront and downtown.

Large bright lower level walkout 3 bedroom in quiet residential neighborhood within walking distance to downtown and lake. Plenty of greenspace and deck and parking. Brand new kitchen fully stocked including oil spices tea coffee. Separate entrance with self-check in. Own free laundry facilities. Close to beach, promenade, festivals, trails, restaurants, shopping and more. 45 mins to Niagara Falls and Toronto. Wi-Fi, freezer, cable, Netflix included. 3 piece bathroom and unlimited towels.

Guest favourite

Home in Bowmanville

4.87 out of 5 average rating, 71 reviews

*Lakeside Retreat: Viva La Vida*

Modern Aesthetic meets Lakeside Luxury with Close Proximity to a lot of Activities! - 3 Beds/1.5 Bath to sleep 8 - 2 Queen size beds & 4 single bunk bed spaces - 60'' Flat-screen TV ( Amazon Prime, Netflix, Smart TV) - Fully equipped kitchen with modern appliances - Coffee Machine - Cozy living room with ample seating - Outdoor furniture for lakeside relaxation - In-suite Washing machine & Dryer - 1000 MBPS Wi-Fi - Washer and dryer for your convenience - 3 car parking space - Large patio

Guest favourite

Flat in The Beaches

4.92 out of 5 average rating, 117 reviews

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

Guest favourite

Cottage in Barker

4.93 out of 5 average rating, 73 reviews

Lake Front Vista & HotTub w/Sun-Thu night discount

Enjoy Spectacular Lakefront views. Relax at your own pace. Take a dip in the spa tub or just enjoy the scenery Very quiet road Speedy internet Fire-pit Enjoy the Niagara Wine Trail 2 Bdrm 6 min to Golden Hill Park 12 min to White Birch Golf course 15 min to Olcott/Burt (fishing charters) 20 min to Waterport/Kent (fishing charters) 50 min to Niagara Falls *Promo: 3rd night or more, will be discounted ~25% (no discount on cleaning and fees, excl 06/23-09/10)

Top guest favourite

Home in Burt

4.94 out of 5 average rating, 109 reviews

Olcott Cottage on the Park

Olcott - This centrally located single family home backs up to Krull Park, a 325 acre park with multiple playgrounds, a splash park, tennis courts, nature trails, softball diamonds, lacrosse fields, horseshoe pits and multiple other activities. It is also within walking distance to downtown Olcott Beach with various restaurants, bars, shops and Newfane Town Marina. It is equipped with all the amenities of home with an updated patio, grill and fire pit.

Superhost

Cottage in Little Britain

4.8 out of 5 average rating, 30 reviews

Cozy Lakeview Cottage | Kawartha Lakes Getaway

Peaceful Atmosphere: Relax in serene surroundings with nature's soothing sounds. Water Access: Short stroll to the water's edge for swims, relaxation, kayaking, and ice fishing. Open Design: Cathedral ceiling, large windows, patio doors for deck access. Family Fun: Bunk beds, teepees, board games for kids' enjoyment. Scenic Views: Panoramic lake and field views from the spacious deck. Enjoy boho decor, coffee bar, firepit, WiFi.

Guest favourite

Cottage in Burt

4.81 out of 5 average rating, 341 reviews

Anchors Away Cottage with Hot tub!

Experience Niagara Falls USA and Lake Ontario like a local! You'll enjoy a restful sleep in our Anchors Away cottage right within walking distance of a public pebble beach. Our quaint cottage is just minutes from Olcott Beach, the Niagara Wine Trail, and world-famous fishing along Eighteenmile Creek and Burt Dam. Niagara Falls is about 30 miles away and the Buffalo metropolitan area is about 40 miles away.

Top guest favourite

Home in Uxbridge

5 out of 5 average rating, 41 reviews

Lakeside Lodge

Skiers dream. Close to Dagmar and Lakeridge ski resorts. Modern, fully renovated beautiful home/cottage. Make some memories at this unique and family-friendly place. Enjoy kayaking canoeing paddle boarding, fishing, outdoor fires, sunsets. Winter offers icefishing, close to ski hills with a warm fireplace to cozy up to after a day on the slopes.