Holiday houses 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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Top Guest favourite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.96 out of 5 average rating, 184 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Top Guest favourite
The interior of the suite features warm wood accents and a combination of natural light and soft lighting. A spacious living area is furnished with a comfortable chair, while an inviting kitchenette is visible in the background. A rustic decor piece stands along one wall, enhancing the cozy ambiance.
Guest suite in Springville
4.98 out of 5 average rating, 235 reviews

Hallmark like cabin suite with panoramic view

Take it easy at this unique and tranquil getaway. Perfect for one or two Adults. Comfortable King Size Bed, private bath, kitchenette (not a kitchen) with airfryer/toaster oven, hot plate microwave & Keurig. Take time away from the hustle and bustle and stay closer to nature in this lovely private suite. Linens, towels and numerous kitchen items provided. Plenty of popular activities and scenery in the surrounding towns and villages. Complimentary WIFI is available but can be unreliable.

Top Guest favourite
A charming lodge is surrounded by vibrant autumn foliage. The wooden exterior features a welcoming porch with seating. A multi-level deck is visible, along with a landscaped yard that includes a stone-styled garden feature. The atmosphere suggests a peaceful retreat in nature.
Home in Colden
5 out of 5 average rating, 41 reviews

The Riehle Lodge

Take it easy at this unique and tranquil getaway nestled in the hills of Colden, NY. You will have you own quiet space in the woods for a romantic getaway or plenty of room for a family retreat. The highlights include 5 acres of woods and plenty of yard for fun and games. The outdoor pavilion boasts a large fireplace, seating and dining for 15, grill and entertainment space. Overlooking the driveway is a large, newly renovated multi-level deck with incredible views of the valley below.

Guest favourite
A charming two-story farmhouse features white siding with maroon shutters. The front porch is adorned with a u-shaped railing and includes a flag. Lush green shrubs frame the entrance, enhancing the welcoming appearance of the home amidst a clear blue sky.
Home in Hamburg
4.98 out of 5 average rating, 106 reviews

Updated authentic family farmhouse

We welcome you to our family farmhouse, which has been in our family for over 150 years. This charming 1860’s home has been lovingly updated and is nestled on 2 acres of land, surrounded by a 20-acre working farm. The home is ideally suited for smaller groups yet has the living space and bedrooms for large groups or multiple families. You will enjoy relaxing in the spacious old farmhouse or activities in the large surrounding yards, with yard games, a fire pit and cooking & dining available.

Top Guest favourite
Apartment in Orchard Park
5 out of 5 average rating, 14 reviews

Charming Modern Farmhouse Lower Loft

Discover this charming modern farmhouse retreat in OPNY, nestled at the edge of Chestnut Ridge Park, home to the renowned Eternal Flame. Minutes from the village, it’s centrally located near East Aurora & Hamburg. Enjoy quick access to Highmark Stadium, 6 mins; ski resorts like Kissing Bridge, 20 mins, Holiday Valley, 35 mins. The Buffalo airport is conveniently 20 mins away. Perfect for relaxation and adventure, this lower loft is an ideal getaway for nature lovers & sports enthusiasts!

Guest favourite
Home in Holland
4.92 out of 5 average rating, 13 reviews

Upscale living on Organic Farm

This is no ordinary farmhouse, but rather an upscale resort facility boasting Brazilian teak floors, expansive quartz countertops, a unique live-edge kitchen table, top-notch leather furniture, plush mattresses, modern bathrooms, and amazing views from every window. Outside there is a three acre lake with a white sand beach, kayaks, forest walking trails, a formal flower garden, an amazing Victorian glass greenhouse with built-in aquariums, and all the fresh in-season fruit you care to pick.

Top Guest favourite
A spacious wooden deck is visible, featuring two rustic benches and a small table. Large windows showcase the interior and reflect greenery from the surrounding trees, creating a connection to nature.
Cabin in Glenwood
4.98 out of 5 average rating, 398 reviews

The Knotty Pine a Romantic Getaway

Our home is a warm and welcoming cabin located 5 minutes from Kissing Bridge ski resort and a short walk to Sprague Brook Park. The park offers three stocked fishing ponds plus hiking and bike trails. It's a 35-minute drive to Buffalo, a 15-min drive to historic East Aurora, 25 minutes to Highmark stadium, and an hour to Niagara Falls. You will have entire access to the cabin,which includes a master bedroom, full kitchen, living room, loft, and bathroom. The cabin is enjoyable year round.

Top Guest favourite
Home in Glenwood
5 out of 5 average rating, 21 reviews

A-Frame in the Hemlocks near Kissing Bridge

This newly renovated 3-bedroom A-frame cabin is directly across from Kissing Bridge Ski Resort, making it the ideal escape for ski lovers, nature seekers, or anyone craving a relaxing retreat. 🛏️ 3 bedrooms (sleeps 6–8) 🛁 Private hot tub for après-ski relaxation 🌲 Spacious deck with string lights for cozy evenings 📶 Wi-Fi & smart TV for streaming and remote work 1 min to Kissing Bridge 5 min to Sprague Brook 20 min to East Aurora 25 min to Orchard Park 35 min to Holiday Valley

Top Guest favourite
The exterior of the timber-frame home is shown, featuring large two-story windows and wood accents. A covered veranda extends from the structure, offering seating. Surrounding greenery and manicured grass enhance the natural setting, inviting a peaceful retreat in the countryside.
Home in East Aurora
4.97 out of 5 average rating, 131 reviews

Timber-frame home on 12 wooded acres

Featured in Buffalo Spree and Artvoice, this timber-frame home features stunning hickory and black walnut interiors illuminated by two-story windows that face the morning sun. Radiant floor heating and earthen-plaster climate design. Wake up in queen and king beds, lounge under covered verandas, and shop right next door at Thorpe’s organic farm store. • 7 minutes from the Village of East Aurora • 24 minutes from Bills stadium • 1 hour from Niagara Falls

Superhost
Home in Orchard Park
4.75 out of 5 average rating, 8 reviews

Two Bedroom Lower Unit in Orchard Park

Located in the Boston Hills, this property is close to everything! Only 10-40 minutes from prime skiing resorts (KB, Holiday Valley, Buffalo Ski Club) and snowmobile trail heads (Chestnut Ridge)! And only 10 minutes to downtown Hamburg and Orchard Park! This property offers the best of both worlds! Come relax, unwind and enjoy all Buffalo has to offer. This house is a split-level home, so stairs are unavoidable. Private laundry facilities available.

Top Guest favourite
Cabin in Ellicottville
5 out of 5 average rating, 47 reviews

Hot Tub, Cabin in Ellicottville, Fire Place

Escape to our newly remodeled 2025 cabin in Ellicottville, NY—perfect for couples or families. Sleeps 4 with modern comforts, including a cozy indoor fireplace, spacious bathroom with heated tile floors & walk-in shower, and fully equipped kitchen. Relax on the large deck overlooking a pond, soak in the hot tub, or gather around the outdoor firepit. Peaceful yet close to ski slopes, hiking, shops & dining—your year-round mountain retreat awaits!!

Top Guest favourite
A spacious balcony extends from the second floor, featuring two outdoor chairs and a small table. The view showcases a lush green lawn leading to the lake, framed by residential houses and trees under a clear blue sky.
Cottage in Fort Erie
4.95 out of 5 average rating, 154 reviews

Steps to the Beach + Lakeviews + HotTub + Elevator

Unwind at this The Red Lakehouse just steps from the beach, featuring a private hot tub, fire pit, and covered balcony with Lake Erie views. Perfect for families, groups, and getaways, this professionally designed home offers 3 bedrooms with private ensuites for ultimate comfort and privacy. Minutes to Niagara Falls, Crystal Beach, and the USA border — yet tucked in a quiet, relaxing neighbourhood. A spotless, thoughtfully curated stay.

Popular amenities for Boston holiday rentals