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Pet-friendly vacation rentals in Middlesex

Find and book unique pet-friendly homes on Airbnb

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 favorite
A vibrant red barn is framed by greenery, with a full rainbow arching across a darkening sky. The barn's luminous white roof contrasts with the moody backdrop, creating a serene countryside image.
Barn in Middlesex
4.98 out of 5 average rating, 244 reviews

Jules Gem

Reconditioned Barn Apartment. One large room with 4 large windows creating much natural light with kitchenette, no oven at this time, but there is a toaster oven & BBQ Grill for your use Overlooking Mountains and situated next to a river. Enjoy the sounds and views of country on this 90 acre property. All new amenities and full bath with shower. Private swimming hole on property, steps from sought after hiking, 12 minutes to downtown Montpelier with fine dining, bars and unique shopping.

Top guest favorite
Cabin in Morristown
5 out of 5 average rating, 226 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 favorite
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
4.97 out of 5 average rating, 195 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 favorite
Home in Waterbury Center
4.99 out of 5 average rating, 149 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 favorite
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, 744 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.

Guest favorite
The exterior of the cabin is presented with a spacious deck featuring seating and a dining area. Two claw foot bathtubs sit on the side, surrounded by a landscaped area with small plants. The cabin is framed by apple trees under a clear sky.
Cabin in Plainfield
4.97 out of 5 average rating, 192 reviews

Magical cabin with amazing views

100 year old , freshly renovated cabin that is in the middle of five 100 year old apple trees with incredible Mountain View’s. The cabin sits 100ft uphill from my 1842 brick farmhouse and is surrounded by apples trees, an ancient elm tree, fields and my berry patches. The huge deck has a dining table, lots of seating and and outdoor shower. Off the side of the deck are two claw foot bathtubs with hot and cold water for you to soak in. Note, tubs aren’t usable during the freezing months.

Top guest favorite
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, 481 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 favorite
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, 256 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 favorite
A charming single-story house sits on a well-manicured lawn, surrounded by lush greenery and flowering shrubs. The exterior features large windows that invite natural light indoors, and a gentle sloping landscape leads towards a serene backdrop of trees.
Home in Moretown
4.96 out of 5 average rating, 198 reviews

Home on Flower Farm near VT’s best skiing & brews!

Country setting adjacent to a flower farm only 3 minutes off 89 perfectly nestled between mountains that boast hiking, skiing and mountain biking and the best of Vermont's brewery and restaurant scene. 20 minutes to Sugarbush and Mad River Glen, 30 minutes to Stowe and 25 minutes to Bolton Valley (night skiing!). With Waitsfield and Waterbury being less than 10 minutes away, it's an easy drive to two of the finest breweries, Lawsons and Prohibition Pig, that Vermont has to offer.

Guest favorite
A cozy cabin features a bright red door and decorative trim. Snow blankets the ground and clings to the surrounding trees. Two green chairs and a small table are placed outside, while a friendly dog sits on the porch, completing the inviting scene.
Guesthouse in Waterbury Center
4.86 out of 5 average rating, 132 reviews

Cozy Cabin at Waterbury Center

Leaf peeping season is here and the latest report is that the leaves are just beautiful! We are located near Stowe, Ben and Jerry's , Burlington. Well-behaved dogs welcomed! One queen bed, air mattresses available. Best for couples, three people is ok, four is tight but do-able. Hot water, microwave, Keurig , refrigerator. Fans, TV (requires you to use your own log in, no cable TV.) Great WIFI. Bathroom is very clean with new toilet, new shower and antique sink. Cozy glamping!

Top guest favorite
A log cabin with a sloped roof is nestled among tall trees, surrounded by a blanket of snow. The clear blue sky provides a bright backdrop to the tranquil scene, with light casting soft shadows on the ground.
Cabin in Groton
4.99 out of 5 average rating, 676 reviews

Peaceful Log Cabin in the Woods

This log cabin is set in the woods in a rural part of northeastern Vermont. Escape the hustle and bustle, clear your mind, and enjoy nature. A great place to get some fresh air or to stay in and take a nap. Beautiful summers for easy hikes and refreshing swims in the lakes of our local Groton State Forest, unbelievable foliage to view from small dirt roads, and tons of outdoor winter activities. Great for a couples getaway, friends weekend, or some quality time with the family.

Top guest favorite
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, 134 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.

Popular amenities for Middlesex pet-friendly home rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ962ﺩ.ﺇ779ﺩ.ﺇ771ﺩ.ﺇ514ﺩ.ﺇ683ﺩ.ﺇ657ﺩ.ﺇ808ﺩ.ﺇ735ﺩ.ﺇ764ﺩ.ﺇ771ﺩ.ﺇ753ﺩ.ﺇ914
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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 ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 3,830 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Middlesex vacation rentals include wi-fi 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!