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Holiday rentals in Middlesex

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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, 252 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 favourite
A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.
Cabin in Morristown
5 out of 5 average rating, 271 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
The exterior of the house is visible, showcasing a modern design with large windows. A spacious deck features patio furniture and an umbrella, surrounded by lush green trees. The clear blue sky creates a serene backdrop for the home, enhancing its privacy.
Home in Waterbury Center
4.99 out of 5 average rating, 160 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
An A-Frame cabin is framed by vibrant fall foliage, showcasing shades of orange and yellow. A spacious deck is visible with seating, and a vintage blue truck is parked nearby. The cabin features large windows that allow natural light to fill the interior.
Cabin in Stowe
4.95 out of 5 average rating, 184 reviews

The Summit House - remodeled unique A-frame

Welcome to The Summit House, a completely renovated A-Frame cabin less than 1 mile to downtown Stowe. Wake up to views of the morning light casting through the forest from your glass wall bedroom. Relax after a day exploring the mountains in the huge spa style rainfall shower. Settle down after dinner around the modern wood burning fireplace while watching your favorite shows on the 50" TV. It's not just a rental, it's an experience. The latest addition to the OM Home Residences collection.

Top guest favourite
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
4.99 out of 5 average rating, 196 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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

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.
Guest house in Waterbury Center
4.99 out of 5 average rating, 276 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

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. Primary bdrm w/ private bath, 2 bdrms that accommodate 4 people w/ shared full bath, one bonus room w/ pull out couch and a 1/2 bath . Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (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 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, 202 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.

Top guest favourite
A wooden bridge leads to the entrance of the treehouse, surrounded by trees displaying autumn colors. The structure features large windows and a unique architectural design, blending nature with handcrafted elements.
Treehouse in Waterbury
4.93 out of 5 average rating, 161 reviews

The Roost - Recharge & Relax

Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.

Top guest favourite
A serene landscape showcases rolling hills silhouetted against a pastel sky at sunset. The subtle gradient of pinks and purples transitions into deeper hues, while trees cresting the hills add depth to the tranquil scene.
Guest suite in Middlesex
4.97 out of 5 average rating, 358 reviews

Morningstar Meadow - your home in Vermont

You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Recent guests claimed heat an issue. It is not. No complaints before or since.

Top guest favourite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 314 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Guest favourite
A spacious living area features a large arched window allowing natural light to fill the room. A wooden coffee table is centered on the floor, while a small desk and chair sit nearby. Potted plants add a touch of greenery, complementing the earthy tones of the walls.
Flat in Waterbury Center
4.9 out of 5 average rating, 240 reviews

B suite Zenbarn 2BR Apt | VIP Perks Live Music

Zenbarn Loft: A Cozy 2-Bedroom Retreat Above Vermont’s Iconic Music Venue 🎶⛰️🍻 Stay in the heart of Vermont, just minutes from Stowe, Waterbury, and top breweries like Alchemist and Lawson’s! This 2-bedroom suite offers a cozy retreat with a kitchenette, fast WiFi, and a private entrance (shared hallway). Live music below creates a vibrant atmosphere. Please message us before booking with any questions to ensure this is the perfect stay for you!

Popular amenities for Middlesex holiday rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹15,938₹16,322₹14,690₹12,674₹12,866₹13,826₹14,786₹13,442₹14,882₹15,362₹12,866₹15,362
Avg. temp-6°C-5°C0°C8°C15°C20°C22°C21°C17°C10°C4°C-2°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Middlesex?

    Middlesex has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Middlesex?

    Experience the best of Middlesex with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Middlesex?

    Four-legged friends are welcome in Middlesex. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Middlesex?

    Yes! Work meets play with ease at over 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Middlesex have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middlesex have a kitchen?

    Absolutely! We offer over 30 apartment rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middlesex have wifi?

    Absolutely! We offer over 70 house rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middlesex have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Middlesex. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Middlesex

  • Total holiday rentals

    Explore 140 holiday rentals in Middlesex

  • Nightly prices starting at

    Middlesex holiday rentals start at ₹3,841 per night before taxes and fees

  • Verified guest reviews

    Over 14,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    130 of Middlesex holiday 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!

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