Holiday rentals in Bolton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Bolton

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

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

Guest house in Hamilton Beach

4.84 out of 5 average rating, 199 reviews

Hamilton Beach Guesthouse with guest Kayaks

LAKEFRONT* renovated lakefront small cottage with two Kayaks situated on the Hamilton Waterfront beach trail. Enjoy fantastic views of the Toronto Skyline and secluded sandy beach. Relax on large deck, overlooking the lake. Right on the waterfront trail, roller blade, bike, kayak or enjoy the sandy beach. Very central for a Niagara winery and Toronto trip. Includes: Smart TV, 1 Parking spot, Tetherball, good Wi-Fi, Fire-pit , BBQ, Kayaks Queen size bed Coffee, condiments &cooking ingredients

Superhost

Home in Hamilton Beach

4.95 out of 5 average rating, 79 reviews

Lakeside Manor | The Ultimate Lakeside Oasis

Welcome to The Lakeside Manor. Truly relax in extravagance, steps from the beach. Enjoy a comfortable California king bed, two queen beds, and plush couch. Experience our overstocked kitchen, large 4 piece bathroom, private balcony with mountain views while overlooking our massive private 16,000sq ft back yard oasis. Enjoy our private parking areas and convenient location close to everything you need! Top restaurants, trails, activities, beach, golf, go cart and more. Great fit for all!

Superhost

Home in Georgina

4.75 out of 5 average rating, 65 reviews

Melody’s Waterfront Cottage

Come and stay in my cozy waterfront cottage With a view so stunning, you won't believe your eyes It's a unique place, with a style all its own You'll feel right at home, in this log house Live your dream off Lake Simcoe, it's a rare find Boater's paradise, fisherman's delight, all in one Just 45 minutes from Toronto, you'll have so much fun With 2 bedrooms, and space for 4 , it's time to unwind you name it, we've got it all Lots of sunshine, and a fire pit to watch the sunset's thrill

Guest favourite

Home in Innisfil

5 out of 5 average rating, 8 reviews

Sand to Snow Getaway

Stay in the upper unit of this charming home, featuring a beautiful kitchen, 1.5 bathrooms, and a spacious living room. The unit offers 2 cozy bedrooms—one with a queen bed and the other with a double bunk bed—perfect for families or small groups. Located within walking distance to the beaches of Lake Simcoe, where you can enjoy ice fishing, snowmobiling, tobogganing, golfing, and skating. Stores and other amenities are just a short drive away. A perfect base for year-round adventures!

Guest favourite

Flat in The Beaches

4.92 out of 5 average rating, 116 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

Top guest favourite

Bungalow in Hamilton Beach

4.94 out of 5 average rating, 157 reviews

Lakefront. Pool. Beach. Fire-pit.

A PERFECT COMBINATION OF LOCATION, LUXURY AND LIFESTYLE. This unique, self contained Studio is only steps from the beach and the beach trail. Enjoy unforgettable beach sunrises. This exclusive beach-sand-bar community is centrally located between Toronto and Niagara. It's a hop, skip & a jump to world renowned restaurants, art crawls, fashion, theatre, culture & more. ADULTS ONLY (21>). Long weekends have a 3 night min.

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.

Top guest favourite

Home in Niagara-on-the-Lake

4.98 out of 5 average rating, 96 reviews

BLUE in NOTL - Lakeside Cottage Historic Old Town

Quaint Luxury Cottage steps to lake and short walk to Historic Old Town. This is the perfect place for daytripping to wineries, breweries, escarpment, lake, theatre and so much more. Watch the most amazing sunsets at near by lakeside park. Cottage is fully equipment and will make you want to come back often. NOTL Short Term License No: 003-2025

Guest favourite

Cottage in Georgina

4.9 out of 5 average rating, 135 reviews

Modern 4-bedroom Lakefront Cottage with Sauna

Bright and airy lakefront cottage in a popular upscale location by lake Simcoe. Open concept layout on the main floor and lot shape give you breathtaking lake views from almost anywhere in the house. Comfortable custom furniture, amazing decor and functional kitchen with everything you need make this place incredible for short or long time stay.

Top guest favourite

Flat in Bronte West

4.91 out of 5 average rating, 11 reviews

Lakeview Retreat | Cozy 3-Bedroom Home w/ Parking

Welcome to your perfect getaway! 🌊✨ This spacious basement unit 3-bedroom home offers stunning lake views and a peaceful retreat just minutes from Oakville’s top attractions. Whether you're here for a relaxing escape, a family vacation, or a work trip, you'll love the modern comforts and serene surroundings this home provides.