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Pet-friendly vacation rentals in Middlesex

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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 R 970 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 3,900 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!

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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Guest favorite
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

4.82 out of 5 average rating, 149 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 138 reviews
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

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.

4.97 out of 5 average rating, 244 reviews
Top guest favorite
Cabin in Morristown

Modern Post&Beam w/ Hot Tub, Waterfall, Mtn. Views

Welcome to The Eddy at Stowe Falls, a thoughtfully designed, quintessential VT getaway. Boasting gorgeous sunrise mountain views, a roaring seasonal waterfall, hot tub, wood beamed ceilings, and a cozy wood stove, this home is your private oasis. Enjoy modern comfort and feel away from it all, while being only 10 min. north of Stowe village with great restaurants & shops, <20 min to Stowe Mtn Resort, and minutes to great hiking/biking/breweries. Experience the sounds, smells, and feels of VT.

4.97 out of 5 average rating, 185 reviews
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

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.

4.88 out of 5 average rating, 800 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 169 reviews
Top guest favorite
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.

4.97 out of 5 average rating, 261 reviews
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

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.

4.95 out of 5 average rating, 209 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 142 reviews
Top guest favorite
A two-story house features a sloped green metal roof, with large windows adorning its beige exterior. A welcoming deck is accessible through a set of stairs, surrounded by landscaped grass and greenery. A storage shed is positioned to the left, tucked among the trees.
Cottage in Moretown

Cozy Cottage in the Mad River Valley

My dad and I built this home from 2015-2019 working mostly on the weekends. We did everything we could ourselves including all the framing, siding, and fine woodworking. It has abundant natural and artificial light and a beautiful deck/porch. We made sure to build a lot of storage space with built in closets, cabinets, and drawers. I am very proud of what we accomplished and I'm so excited to be able to share our creation with guests.

4.95 out of 5 average rating, 231 reviews
Top guest favorite
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.
Home in Stowe

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.

4.98 out of 5 average rating, 203 reviews
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

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.

4.96 out of 5 average rating, 158 reviews

Popular amenities for Middlesex pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
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

4.97 out of 5 average rating, 303 reviews
Guest favorite
Home in Stowe

SylvanRhapsody-Stowe Village OutDoor Hot-tub!

4.92 out of 5 average rating, 145 reviews
Top guest favorite
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.
Home in Stowe

Cozy Mountain Home w/Million $ View

4.97 out of 5 average rating, 130 reviews
Top guest favorite
The main living area features high wooden ceilings and open spaces with natural light. A wooden staircase leads to a loft area, accented by greenery and artistic decor. A comfortable couch and a few wooden furnishings are positioned for cozy gatherings.
Home in Plainfield

Mountain Getaway

4.86 out of 5 average rating, 294 reviews
Top guest favorite
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

4.89 out of 5 average rating, 122 reviews
Guest favorite
The farmhouse is shown at dusk, with warm light emanating from numerous windows, creating a welcoming glow. A covered porch extends towards the entrance, flanked by a well-kept yard. The structure features contrasting exterior colors, emphasizing its rustic charm in a serene environment.
Home in Morristown

5 Bedroom Historic Chambers Farmhouse

4.92 out of 5 average rating, 123 reviews
Guest favorite
The exterior of a contemporary concrete home is showcased, featuring a unique asymmetrical roof design with solar panels. The structure is surrounded by trees, and large windows allow glimpses into the interior. Natural stone accents provide contrast against the smooth concrete façade.
Home in Warren

Architectural House Prickly Mountain

4.9 out of 5 average rating, 114 reviews
Top guest favorite
Home in Stowe

Vermont Cedar Cottage | Fireplace & Pond Views

4.96 out of 5 average rating, 164 reviews

Pet-friendly home rentals with a pool

Guest favorite
A private outdoor area showcases a swimming pool with a colorful floating toy. The pool is surrounded by a wooden deck and features lounge chairs. In the background, a light gray house with a porch and seating areas is visible, framed by mature trees and shrubs.
Apartment in Williamstown

Cozy/Private, close to hospital, i-89

4.91 out of 5 average rating, 185 reviews
Top guest favorite
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.
Home in Stowe

EPIC Stowe Getaway - Great For Families & Friends

4.98 out of 5 average rating, 313 reviews
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

4.87 out of 5 average rating, 144 reviews
Top guest favorite
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

4.95 out of 5 average rating, 108 reviews
Top guest favorite
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

4.98 out of 5 average rating, 185 reviews
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, 193 reviews
Guest favorite
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

4.77 out of 5 average rating, 279 reviews
Guest favorite
A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.
Yurt in Randolph

Lower Yurt Stay on VT Homestead

4.94 out of 5 average rating, 482 reviews

Private, pet-friendly home rentals

Top guest favorite
A modern kitchen features light grey cabinets and a stylish island with a dark countertop. Stainless steel appliances include an oven and hood vent. Natural light filters through a window, illuminating the herringbone backsplash. A red area rug adds warmth to the wooden floor.
Apartment in Montpelier

Modern & Central Treehouse Apartment

5.0 out of 5 average rating, 109 reviews
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

Waterbury Center Guest Bedroom - 244 Howard

4.94 out of 5 average rating, 496 reviews
Guest favorite
Cabin in Calais

Fabulous Fall Foliage on water in the heart of VT

4.87 out of 5 average rating, 124 reviews
Top guest favorite
An open living space features a cozy seating area with a modern sectional sofa and a sleek coffee table. Natural light illuminates the room, with decorative plants and artwork enhancing the ambiance. The kitchen area showcases contemporary cabinetry and appliances, accompanied by exposed brick accents and a tin ceiling.
Apartment in Montpelier

Miles Court 1BD Downtown Montpelier

4.96 out of 5 average rating, 467 reviews
Top guest favorite
Cabin in Worcester

Pet Friendly Cozy Treetop Cabin near Mt Worcester

4.96 out of 5 average rating, 250 reviews
Top guest favorite
An aerial view captures a modern farmhouse-style condo surrounded by trees with vibrant autumn foliage. The property features a wide deck, outdoor space, and a gazebo to the side, complemented by a manicured lawn and gravel pathway leading to the entrance.
Condo in Stowe

Renovated 4BD House: Hot Tub, Sauna & Backyard

4.97 out of 5 average rating, 158 reviews
Superhost
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

4.96 out of 5 average rating, 372 reviews
Guest favorite
A spacious living room is highlighted by a black brick feature wall, accommodating a wall-mounted TV and a stylish fireplace. Natural light floods the space through large windows, and comfortable seating is arranged around a wooden coffee table. A neutral color palette enhances the inviting atmosphere.
Condo in Stowe

Modern Condo Filled with Natural Sunlight

4.85 out of 5 average rating, 121 reviews

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 3,687 ZARR 3,962 ZARR 3,202 ZARR 2,781 ZARR 3,266 ZARR 3,283 ZARR 3,557 ZARR 3,234 ZARR 3,363 ZARR 3,315 ZARR 3,234 ZARR 3,606 ZAR
Avg. temp-6°C-5°C0°C8°C15°C20°C22°C21°C17°C10°C4°C-2°C

Destinations to explore