Pet-friendly vacation rentals in Middlesex

A large house featuring a blend of stone and timber architecture is set against a backdrop of lush greenery. The exterior showcases a prominent gable roof, large windows, and a welcoming porch. A separate structure with a barn-like design is visible in the background.

4.97 out of 5 average rating, 131 reviews

Cozy Mountain Home w/Million $ View

Privacy, awesome views of Trapp Family Lodge and Stowe Mountain Resort. 5 min drive to town and 10 min to ski area. Home to famous visiting musicians thru the years including the recording of Phish's " Story of the Ghost ". Family or a group love it! My home offers a great open space to relax in front of the fire and enjoy the company of friends and/or family. It easily accommodates a lot of people. The entire house is for rent although less is open for discussion as well, just ask. I stay in an apartment next door so am readily available should anyone have a question. In the winter it is best to have snow tires or four wheel drive to access the property. I am around however to assist if you need help getting up the hill. The road and driveway are both maintained very well but this is Vermont and we get a lot of snow!

4.82 out of 5 average rating, 153 reviews

A white farmhouse is set against a clear blue sky, surrounded by lush greenery and large trees. A private pool reflects the house and trees, creating a serene outdoor space. A rustic barn can be seen in the background, indicating the property's charm.

Home in Plainfield

Mountain View Farmhouse w/ Orchard, Pool is Open!

This magical property is Vermont at its finest. Bring the whole family to this idyllic farmhouse with panoramic mountain views, large private pool, apple orchard, flower gardens, fire pit and much more. Be as free as you imagine on 14 private acres of lawn, perennial gardens, fruit trees and lush woods with a meandering stream. Let the kids swim in the pool all day while you read in the shade of old locust trees while taking in one of the best views in Vermont.Find us on insta: @upper_east_eden

4.99 out of 5 average rating, 140 reviews

The farmhouse is displayed with a classic white exterior and a metal roof. A welcoming front porch is flanked by steps leading up to the entrance. Surrounding fields stretch into the distance beneath a clear blue sky, showcasing the home's peaceful rural setting.

Home in East Montpelier

The 1919 Mountain Farmhouse, new hot tub and patio

Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

4.97 out of 5 average rating, 251 reviews

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

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.

4.88 out of 5 average rating, 803 reviews

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

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.

4.99 out of 5 average rating, 172 reviews

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

Stunning Views near Stowe /Mountain private home

Retreat and relax at this incredibly located & 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 minutes to the attractions of Stowe, Waterbury and Mad River Valley. Enjoy the hiking trails very close to this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

4.97 out of 5 average rating, 263 reviews

The log cabin features a charming exterior with a prominent stone chimney and rustic red accents. It is surrounded by lush greenery and tall trees, with a serene yard that conveys a peaceful retreat in nature. A welcoming wreath adorns the front door.

Cabin in Stowe

Charming log cabin w/ fireplace in Stowe village

The Ginger House: experience the warmth of this charming rustic log cabin, situated in the woods but close to the main village of Stowe. The open floor plan allows you to be in the new kitchen while still enjoying the real fireplace. Also located on the first floor is a full bath and spacious bdrm. Upstairs is where you’ll find the master with full bath. There is a large deck and fire pit which is great for just hanging out. All this and easy access to the Mountain Road shuttle.

4.95 out of 5 average rating, 210 reviews

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

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.

4.99 out of 5 average rating, 146 reviews

A hot tub emits steam under the soft glow of string lights, creating a relaxing ambiance. The wooden deck features outdoor seating, inviting guests to enjoy the night. The rustic home blends with the surrounding nature, offering a peaceful retreat.

Home in Waterbury Center

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub

Welcome to our cozy retreat nestled in the picturesque town of Waterbury, Vermont. This newly renovated spacious and modern home is perfect for families or groups looking for a comfortable and stylish retreat. With its prime location, you’ll have easy access to local attractions, outdoor activities, renowned craft beer scene, world-class skiing, hiking trails, and breathtaking Mountain View’s - making it an easy getaway choice for nature lovers and outdoor enthusiasts.

The house is set against a backdrop of vibrant fall foliage, with a blend of yellow and red leaves surrounding it. Large windows reflect the colors of the trees, while the modern architecture adds to its charm. The scene conveys a harmonious connection with nature.

4.98 out of 5 average rating, 203 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

4.96 out of 5 average rating, 160 reviews

Home in Waterbury

Cozy Hideaway w Hot Tub — Bike, Hike, Play & Relax

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.

4.93 out of 5 average rating, 136 reviews

Home in Huntington

Happy Hollow Barn

This one of a kind 4 bedroom home was built in 2018. We refinished an old barn frame from Waitsfield, VT and had it moved to our property. The hand-hewn frame of this early 1800's barn is a piece of art in itself. We have used as much of the original structure as we could to create a warm, rustic, and inviting space for you to get away from reality for a little while. Come enjoy a peaceful retreat in the mountains of Vermont.

Popular amenities for Middlesex pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 252 reviews

A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.

Home in Roxbury

Captain Tom's Cabin - Secluded Vermont Getaway

4.89 out of 5 average rating, 122 reviews

The historic guest house is surrounded by a blanket of fresh snow, highlighting its charming architecture. The two-story building features a prominent front porch and distinctive chimneys, set against a backdrop of gently falling snowflakes and a clear winter sky.

Home in Waterbury Center

7 Bedroom/5.5 Bath House Near Stowe

4.97 out of 5 average rating, 306 reviews

The red wooden house features a welcoming entryway with a prominent front door framed by large windows. Bright green foliage lines the path, enhancing the natural setting. The garage is visible on the left, with sunlight illuminating the exterior.

Home in Hyde Park

CLASSIC VT STYLE

4.96 out of 5 average rating, 165 reviews

Vermont Cedar Cottage | Fireplace & Pond Views

4.99 out of 5 average rating, 364 reviews

The hillside home is framed by trees, featuring a red exterior with white trim. A small deck with two red chairs is visible in front, offering a cozy outdoor space to relax among the greenery.

Home in Corinth

Dawnside - Green Mtns Home with White Mtns View

4.92 out of 5 average rating, 145 reviews

SylvanRhapsody-Stowe Village OutDoor Hot-tub!

4.98 out of 5 average rating, 104 reviews

Home in Woodbury

Lakewood Lodge & Hot Tub

4.99 out of 5 average rating, 178 reviews

The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.

Home in Starksboro

Forest Hideaway

Pet-friendly home rentals with a pool

Superhost

A serene lake scene is framed by lush greenery and trees. A canoe rests on the grassy shore, with soft water reflections of the surrounding landscape. The sky displays gentle pastel hues, indicating a calm evening atmosphere.

Home in Haverhill

Lakefront Peaceful Getaway in Mountain Lakes

4.8 out of 5 average rating, 196 reviews

A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.

4.98 out of 5 average rating, 315 reviews

EPIC Stowe Getaway - Great For Families & Friends

Apartment in Williamstown

Cozy/Private, close to hospital, i-89

4.91 out of 5 average rating, 187 reviews

4.98 out of 5 average rating, 103 reviews

Villa in Stowe

World-Class Villa @ Trapp & Stowe

4.95 out of 5 average rating, 109 reviews

An aerial view captures a spacious, one-story home surrounded by expansive green lawns and wooded areas. The property features a detached garage and a shed, with ample outdoor space visible for recreational activities.

Home in Barre

Charming Barre Getaway

Superhost

Two friendly donkeys stand side by side on a grassy hillside, framed by a clear blue sky with clouds scattered above. Their ears are perked up, and their coats display shades of gray and brown, creating a charming scene of farm life.

Farm stay in Marshfield

UNIQUE, BEAUTIFUL HOME w/ 30 ACRE FARM

4.86 out of 5 average rating, 146 reviews

4.98 out of 5 average rating, 188 reviews

A red-painted two-story house is framed by lush green grass and colorful flower beds. A welcoming porch features two white chairs and wooden barrels. A friendly dog is seated at the entrance, adding a homely touch to the exterior.

Place to stay in Johnson

Château Chavis

4.78 out of 5 average rating, 281 reviews

A seasonal outdoor pool is surrounded by a fenced area, featuring lounge chairs and a colorful hammock. Lush green trees provide shade, while sunlight reflects off the clear water. A nearby cottage is visible in the background, adding to the tranquil setting.

Cottage in Stowe

Cute Cottage - Poolside - Minutes To Activities

Private, pet-friendly home rentals

4.96 out of 5 average rating, 251 reviews

Cabin in Worcester

Pet Friendly Cozy Treetop Cabin near Mt Worcester

5.0 out of 5 average rating, 212 reviews

A spacious cabin is set in a lush green landscape, surrounded by tall trees. Large windows dominate the front, allowing natural light to fill the interior. The sloped grassy yard leads to a relaxing outdoor space, perfect for enjoying the serene woodland views.

Cabin in Enosburg

The Rustic Retreat at Twin Ponds

Guesthouse in Waterbury Center

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.

A true Vermont get-away cabin in the woods

4.98 out of 5 average rating, 291 reviews

Guest suite in Waterbury Center

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.

Waterbury Center Guest Bedroom - 244 Howard

4.94 out of 5 average rating, 499 reviews

4.96 out of 5 average rating, 374 reviews

A farmhouse is positioned in a scenic landscape, with a gravel driveway lined by greenery leading towards it. The sunrise casts warm tones across the sky, reflecting on puddles in the foreground, while a distant tree stands amidst the open fields.

Farm stay in Elmore

Cozy rustic Cottage // Close to Stowe

4.97 out of 5 average rating, 159 reviews

Condo in Stowe

Renovated 4BD House: Hot Tub, Sauna & Backyard

4.94 out of 5 average rating, 266 reviews

A sun-filled living area features large windows that offer views of the surrounding trees. A cozy seating arrangement includes a blue couch and a brown accent chair. A low coffee table sits atop a vibrant, striped rug, complemented by a soft bean bag nearby.

Cabin in Moretown

Waldhaus - Modern Forest Cabin