Holiday rentals in Boston

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Top-rated holiday rentals in Boston

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

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Guest favourite
A serene view of the cabin is reflected in the tranquil pond, surrounded by lush trees. Red outdoor chairs are positioned nearby, inviting relaxation by the water's edge, while the cabin's simple design complements the natural landscape.
Cabin in Windham Centre
4.92 out of 5 average rating, 279 reviews

The Kiln - Stay Longer Save More!

Escape life's bustle & retreat to this 4-season cabin, which sits on an 80 acre farm overlooking a tranquil pond. Cozy up inside by the wood stove, play some of the many games provided, or kick your feet up & catch up on your favourite shows as satellite & wifi are accessible. Get outdoors to wonder the fields and go for long forest walks along the many trails, or sit around the fire pit roasting hot dogs and marshmallows! Make sure to keep an eye though, as you're bound to see some wildlife!

Top guest favourite
A repurposed shipping container is set within a forested area, surrounded by tall trees. A circular fire pit made of smooth stones can be seen in the foreground, with a fire crackling. A hammock is hung between two trees nearby, and two chairs are positioned on a wooden deck.
Shipping container in Simcoe
4.97 out of 5 average rating, 138 reviews

Little Can in the Pines - Bunkie No. 1

*NO hydro/power/electricity *NO running water *NO flush toilet (outhouse only) *NO Wi-Fi *NO street lights (it's dark at night) *NO sheets, blankets, pillows - Queen *NO cookware, plates, utensils etc. *HEATED seasonally from Oct - May *Outdoor shower - operates seasonally *Poor cell signal (except Rogers) *Very private *Far from road - 800 ft *Dogs welcome *Firewood for sale *BBQ & propane provided w/ tongs & spatula *Bunkies are 400 ft apart from each other We look forward to hosting you!

Guest favourite
A spacious bedroom features an elegant white bed with decorative pillows and a textured quilt. A woven basket sits on the bed, adding charm. Soft light is provided by hanging chandeliers, and a cozy seating area is visible, contributing to a tranquil ambiance.
Home in Waterford
4.91 out of 5 average rating, 121 reviews

Vintage Farmhouse with Hot Tub on Vineyard

Our tranquil Farmhouse at Bonnieheath Estate blends vintage country charm, creating a warm and inviting retreat for up to 8 guests. This beautifully styled three-bedroom, one-bathroom Farmhouse is on the main and upper floor of the building and does not share amenities with the Cellar Suite which is a separate unit on the lower floor. Perfect for relaxing, quiet gatherings, enjoying a peaceful countryside escape, steps away from the working Vineyard and Lavender farm at Bonnieheath Estate.

Top guest favourite
A comfortable bed is dressed in a white quilt with subtle texture, complemented by decorative pillows in various colors. A framed artwork featuring a tree hangs above the bed, while soft lighting enhances the serene environment of the room.
Flat in Port Dover
4.96 out of 5 average rating, 47 reviews

Country Apartment Retreat

Relax in this calm, stylish space set in the heart of Norfolk county. Parking & coded access insure smooth entry. You are minutes from the palm trees on Port Dover’s beach, the Theatre and multiple restaurant patios. Live a country experience while exploring a refurbished barn and meet the resident critters. You have quick access to the Lynn Valley trails, breweries, and wineries in the area. After a beautiful drive you will experience the wonders of our World Biosphere at Long Point.

Guest favourite
A modern kitchen is equipped with black cabinetry and stainless steel appliances. A central island with seating for four is paired with a double sink. Under-cabinet lighting and large windows contribute to a well-lit cooking area, enhancing the inviting ambiance.
Flat in Brantford
4.94 out of 5 average rating, 96 reviews

The Station House

Don’t judge this book by it’s cover. Steps from VIA Rail Brantford this unique apartment awaits your stay. The fully equipped kitchen with a dishwasher and gas stove will make your stay feel like your at home if you love to cook. Washer/dryer in unit for those extended stays. The bathroom will leave you speechless and mesmerized with its eclectic style. The cozy bedroom has 3 skylights to let that natural light in. Apartment is very soundproof so you only feel the odd train rumble by.

Top guest favourite
Guest suite in Hamilton
5 out of 5 average rating, 64 reviews

Summertime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Guest favourite
A modern guesthouse exterior is presented, featuring a contrasting white facade with black accents. Large windows allow for ample light, while the garage doors reflect a sleek design. The gabled roof adds architectural interest to the overall structure.
Guest house in Norfolk
5 out of 5 average rating, 9 reviews

Scenic & Cozy Guesthouse

Cozy guesthouse nestled on 50 acres of natural beauty. Perfect for nature lovers. Enjoy a comfortable stay in a thoughtfully designed space, complete with a cozy bedroom, a well-equipped kitchen, and a welcoming living area. Large windows let in plenty of natural light and provide views of the surrounding landscape. Explore private nature trails, perfect for hiking, birdwatching, or simply enjoying a tranquil stroll while enjoying all the comforts of home.

Guest favourite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guest house in Lincoln
4.96 out of 5 average rating, 312 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 27-JULY 6 JULY 8-18 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

Guest favourite
A spacious living area features a dark sectional sofa with decorative pillows, complemented by a wooden coffee table. A light blue area rug covers the floor, and wall art decorates the walls, creating a relaxed atmosphere. Natural light is provided by recessed lighting.
Home in Oakland
4.95 out of 5 average rating, 109 reviews

Luxury Oasis with Hot Tub/Pool

Forget your worries in this spacious and serene space. Our Apartment offers you the chance to get away from it all with luxurious extras from a romantic soak in our hot tub or swim in our seasonal pool. Spoiled with robes to use during your stay, or a coffee at our coffee, tea, and hot chocolate bar. Enjoy a romantic fire under the stars in a shared firepit, or relax in your beautiful patio area with your own bbq and beautiful outdoor lighting.

Guest favourite
The open-concept living area showcases a gray sofa paired with two elegant chairs featuring gold accents. A small, dark table is positioned between them. Natural light enters through a nearby window adorned with soft curtains, enhancing the inviting ambiance.
Guest house in Brantford
4.86 out of 5 average rating, 218 reviews

Charming Garden Guest House with Modern Comforts

Take it easy at this unique and tranquil getaway and enjoy a delightful stay in a separate studio garden suite for your Brantford trip. The guest house is equipped with AC, heating, and WIFI to make your stay comfortable. Our guest house is less than five minutes away from Hwy access, restaurants, bars, parks, and the Wayne Gretzky Sports Center. A great location for you to discover Brantford the best way. We look forward to hosting you!

Top guest favourite
A cottage is surrounded by vibrant red foliage, showcasing a blend of natural colors. The exterior features light wood siding and a tiled roof, with large glass doors leading to a patio area. Lattice work adorns parts of the structure, adding texture and visual interest.
Guest house in Delhi
4.97 out of 5 average rating, 177 reviews

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

Superhost
Home in Simcoe
4.76 out of 5 average rating, 153 reviews

Oliver's Tiny Home In The Forest | Sauna & Hot Tub

Escape to the heart of a Carolinian forest in Simcoe, Norfolk County — a private tree farm sanctuary designed for those who crave stillness. Sink into the hot tub, warm your soul in the wood-burning sauna, or brave the cold plunge bucket on warm days. Surrounded by towering trees and birdsong, this cozy retreat welcomes couples, friends, and solo adventurers year-round. Unplug. Breathe. Belong to the forest.

Popular amenities for Boston holiday rentals

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