Pet-friendly vacation rentals in Middlesex

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Top-rated pet-friendly home rentals in Middlesex

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
Cabin in Enosburg
4.99 out of 5 average rating, 191 reviews

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

Top guest favourite
Cabin in Morristown
5 out of 5 average rating, 254 reviews

Cady’s Falls Cabin

Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Top guest favourite
Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.
Barn in Morristown
4.98 out of 5 average rating, 210 reviews

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

Top guest favourite
An open living area features a wooden dining table surrounded by black chairs. A cozy lounge area includes a navy blue sofa and a wooden coffee table, complemented by a patterned area rug. Exposed beam ceilings add a rustic touch to the bright space.
Home in Waterbury Center
4.99 out of 5 average rating, 158 reviews

Stunning Views near Stowe / Private mountain home

Retreat and relax at this incredibly located and uniquely designed home nestled in the heart of ski country. This three bedroom, two bathroom vacation home is perfect for families or couples looking to enjoy Vermont's beauty and recreation. Very private location yet close to the amenities of Waterbury, Stowe and Mad River Valley. Enjoy the hiking trails, minutes away from this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

Guest favourite
The exterior of the duplex is showcased, featuring a welcoming porch with two umbrellas over a seating area. Steps lead up to the porch, surrounded by lush greenery and neatly arranged flower beds, and the house is embraced by mature trees.
Apartment in Montpelier
4.87 out of 5 average rating, 757 reviews

Entire 2nd Floor Walk to Montpelier

Five minute walk to the prettiest and coolest state capital in the country. Entire second floor duplex with separate entrance up a flight of stairs. Beautiful porch. Perfect base to explore Vermont; hiking, skiing, biking. Hosts live downstairs. Dogs are welcome with conditions. (Note the reservation requirements) Limit 4 people. (Includes toddlers and infants) If you are a skier, we're e less than an 40 minutes to major Ski areas. You won't have to pay resort prices and have a more room.

Top guest favourite
Two white Adirondack chairs are positioned on a grassy expanse, surrounded by autumn foliage. Trees with vibrant orange and yellow leaves create a scenic backdrop against a clear blue sky, showcasing the natural beauty of the 8-acre property.
Home in Waterbury Center
4.96 out of 5 average rating, 142 reviews

Peaceful setting with Mountain Views

Rent the entire house. Large primary bdrm w/ private bath and 2 bdrms that accommodate 4 people w/ a shared full bath, one bonus room with pull out couch. Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (available from Memorial Day till Thanksgiving), outdoor fire pit, all on 8 acres. Located centrally to three ski resorts, mountain biking, hiking , kayaking, swimming, you name it. An inviting home in any season!

Top guest favourite
A cozy sitting area features a couch and an armchair, complemented by decorative cushions. Wall art is displayed above a television, and a kitchenette is visible in the background. Warm lighting enhances the inviting atmosphere in this thoughtfully arranged space.
Guest suite in Waterbury Center
4.94 out of 5 average rating, 482 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room has a separate entrance located off a covered, back porch with a small table and chairs for summer use. There is adjustable heat and cool air from the wall mounted air-source, heat pump. The little kitchen alcove is convenient for coffee or tea or a light meal (toaster oven, single induction “hot” plate, water heater) We live in a historic building. Our neighborhood is very close to Rte 100. Waterbury village and Stowe are nearby too with skiing, hiking and biking.

Top guest favourite
The cottage, featuring a wooden exterior and large windows, is surrounded by greenery and natural rock formations. A stone pathway leads to the entrance, which is sheltered by an overhanging roof. Sunlight illuminates the peaceful setting, highlighting the rustic charm of the structure.
Guesthouse in Waterbury Center
4.99 out of 5 average rating, 273 reviews

A true Vermont get-away cabin in the woods

Badger Cottage offers a true rustic Vermont experience nestled in the woods with spectacular views and a quiet and peaceful ambiance. Once a barn, carefully reconstructed on the owners’ property, and modernized to today’s standards, this post and beam cabin is warm and cosy in winter and cool in summer. Well behaved dogs are very welcome and will enjoy the walks in the woods. Covid vaccinations are required. The owners live in an adjacent house with their very friendly Border Terrier

Guest favourite
The cottage is nestled among trees, positioned on a gentle slope beside a flowing brook. A wrap-around deck extends from the structure, providing views of the surrounding nature. The peaceful sounds of water accompany the serene atmosphere created by the lush greenery.
Cottage in Morristown
4.93 out of 5 average rating, 104 reviews

The Cottage on Sterling Brook

Escape and relax in the peaceful atmosphere of Sterling Brook. 🍁 Comfortable & cozy interior leads onto a wrap-around deck right on the banks of Sterling Brook, beautiful in every season. 🍁 Keep an eye out for the local otters playing in the brook while drinking your morning coffee. 🍁 This serene hideaway offers a peaceful retreat in nature, leaving you rested and recharged. Conveniently located on the outskirts of Stowe. Sleeps 3. Dog-friendly with approval. 🍁🦦🍁

Top guest favourite
Cabin in Worcester
4.95 out of 5 average rating, 232 reviews

Pet Friendly Cozy Treetop Cabin near Mt Worcester

Come get Vermonty like a local. A quiet sanctuary home base for adventure. Pick raspberries, climb a mountain, and cool off in a swimming hole. Far away from it all yet close to all you want to do. Wake up to a tree top sunrise. Have coffee in the hammock while watching the birds. Spend your days skiing fresh powder or apple picking and return home to quirky records, books, and games. Well-behaved pets welcome. Extensive seasonal local guide upon booking.

Top guest favourite
A spacious living area features a large, sectional grey sofa adorned with colorful cushions. A coffee table sits in front, accompanied by a small decorative bowl. Natural light filters through large windows, enhancing the warm wooden flooring and inviting atmosphere.
Home in Waterbury Vermont
4.95 out of 5 average rating, 150 reviews

Cozy Hideaway w Hot Tub — Perfect for Ski Weekend!

Welcome to our lovely 1865 Waterbury Village Hideaway. We are located 1/2 mile from the very best Mountain Biking trails, less than 1 mile to great food and beer, access to more than 7 Ski Resorts, including Stowe, Sugarbush & Killington, and 30 minutes from Burlington and the Waterfront. Use this Hideaway to take advantage of everything Vermont has to offer and relax in the soothing waters of our Hot Tub at the end of the day.

Guest favourite
An open living area features wooden walls and a light wood floor. A small kitchenette is visible with seating at a bar. A table with two patterned chairs is positioned next to a doorway, leading to the stairs. Natural light enters through a nearby window.
Apartment in Montpelier
4.9 out of 5 average rating, 102 reviews

Travelers Oasis in Montpelier

We are SuperHosts! Our average is 4.86 stars. We recently had to change the hosting account for this apartment: To see reviews: http://airbnb.com/h/travelers-oasis-reviews this listing is absolutely the same. Travelers will experience a beautiful and comfortable resting space in this upstairs apartment in the heart of Vermont's state capital, Montpelier. Uniquely renovated space that gives one the impression of being in a boat.

Popular amenities for Middlesex pet-friendly home rentals

When is the best time to visit Middlesex?

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Avg. price$360 CAD$291 CAD$288 CAD$192 CAD$255 CAD$246 CAD$302 CAD$274 CAD$285 CAD$281 CAD$274 CAD$306 CAD
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Quick stats about vacation rentals that are pet-friendly in Middlesex

  • Total vacation rentals

    Explore 30 vacation rentals in Middlesex

  • Nightly prices starting at

    Middlesex vacation rentals start at $82 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Middlesex vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middlesex rentals

  • 4.9 Average rating

    Middlesex stays are highly rated by guests—averaging 4.9 out of 5!