Holiday houses 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.

%{current} / %{total}1 / 1
Top Guest favourite
A spacious studio apartment features a high, sloped ceiling and large windows that provide views of the surrounding greenery. The area includes a queen bed, cozy seating options, and a well-equipped kitchen with a breakfast bar, creating a welcoming and functional living space.
Guest suite in Waterbury Center
4.87 out of 5 average rating, 213 reviews

Cozy Mountain Retreat with a View of Mt Hunger

Nestled in the heart of Vermont's best skiing, hiking, dining + golfing right between Waterbury and Stowe. We're just minutes to downtown yet the private driveway that opens to 10 acres feels like you're a world away. The apartment has a private locking entrance through a shared garage, well stocked kitchen, cozy sitting area with a view of the mountains, full bathroom, memory foam mattress and blackout shades. We are family friendly with a highchair, pack n' play + changing table upon request!

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 guest house nestled among trees features a rich red exterior with a standing seam metal roof. The landscape is adorned with lush greenery and flowering plants, creating a serene environment. Two prominent windows provide natural light while maintaining privacy.
Cottage in Jericho
5 out of 5 average rating, 167 reviews

Selkie’s Shed

This guest house has been built and designed by my husband and I. It sits behind our house with private walking/biking trails right out your door. The design is modern with natural warm colors and tucked away in the trees. The loudest noise you will hear are the owls hooting and a faint distant train whistle two times a day. Our mission is to create an atmosphere of tranquility, calmness and peace. We offer mother nature outside your door with easy access to all the activities you desire.

Top Guest favourite
A cozy bedroom space is highlighted by warm wooden walls and twinkling string lights. A spacious bed is dressed in soft linens, adorned with decorative pillows. A large TV is mounted above a dresser, with an inviting area rug complementing the natural wood flooring.
Loft in Duxbury
4.98 out of 5 average rating, 272 reviews

Cozy Studio/Romantic Getaway

Take it easy at this cozy studio which is nestled in the hills of the beautiful Duxbury Vermont. Offered year round so that our guests can enjoy all that Vermont has to offer such as nearby skiing, changing leaves, hiking and so much more! Guests will enjoy their own private space with access to many amenities such as a full kitchen, private entrance, a queen bed, free WIFI and so much more! So grab a mug and sit back and relax next to the gas fireplace! You will want to return every season!

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, 272 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
A unique bow roof home sits nestled among trees, illuminated warmly against a backdrop of a star-filled night sky. The expansive windows reflect the twinkling stars above, creating a serene atmosphere for stargazing and relaxation.
Home in Starksboro
4.99 out of 5 average rating, 203 reviews

The Spring Hill House

Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Top Guest favourite
A cozy studio space is shown, highlighting a gray dresser and a red chair with a patterned cushion. The open kitchen area is visible in the background, featuring shelving with kitchen items, a small dining table, and modern appliances, all under soft lighting.
Apartment in Montpelier
4.96 out of 5 average rating, 172 reviews

Contemporary Studio in Montpelier

Keep it simple at this peaceful and centrally-located place just minutes from downtown Montpelier. A contemporary studio set within the charm of a historical building. Relax under the apple tree with your morning coffee or take a five minute walk into town for freshly-baked pastries. Discover what our vibrant little city has to offer without ever getting into your car. No matter the season, there are great places nearby to explore for swimming, hiking, biking, and skiing.

Top Guest favourite
A panoramic view reveals rolling green mountains under a partly cloudy sky. The foreground features a lush meadow filled with tall grass, bordered by a tree line. The vibrant greens of the trees contrast beautifully with the scenic backdrop, inviting a sense of tranquility.
Guest suite in Waterbury Center
4.95 out of 5 average rating, 304 reviews

Farmhouse with Sunset Mountain Views

Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe Village, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

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
4.92 out of 5 average rating, 142 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 private mountain home is nestled among lush greenery, featuring a wooden exterior and a metal roof. The structure is complemented by a welcoming porch and surrounded by a neatly maintained lawn, creating a serene atmosphere against the forest backdrop.
Home in Middlesex
4.94 out of 5 average rating, 195 reviews

True Mountain House

This is a very private mountain home surrounded by green and peace. Your private forest. Amazing Views. Very romantic. Open layout. Lots of light. Wood floors and electric heating. Very quiet, relaxing and cozy. It has a decompressing effect on it's guests. Perfect to rest your head. Not suitable for children under 12 years old. Amazing gourmet kitchen. WE HAVE HIGH SPEED INTERNET. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.

Top Guest favourite
The exterior of the guesthouse is shown, featuring a white wooden facade with multiple windows. A prominent cupola tops the structure, reflecting sunlight under a clear blue sky. Lush green trees and shrubs surround the building, enhancing the serene ambiance of the area.
Guesthouse in Vergennes
4.98 out of 5 average rating, 132 reviews

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

Guest favourite
A warm living area features a corduroy sofa adorned with colorful throw pillows. Nearby, a decorative lamp stands on a side table, and a wooden cabinet adds storage space. Artwork depicting a tree hangs on the wall, complemented by natural light filtering through patterned window coverings.
Apartment in Montpelier
4.96 out of 5 average rating, 113 reviews

Stylish Montpelier 2BR Apt. Walk to town

Stylish renovation in this sunny 2 bedroom Montpelier apartment. Entire second floor of a two unit house. Two large bedrooms, open living/dining room with wood floors throughout. Roku tv, large covered porch from living room and primary bedroom and fully equipped kitchen including washer/dryer, dishwasher, gas stove and microwave. 10 minute walk to downtown. Centrally located for skiing, hiking and exploring. Parking on site.

Popular amenities for Middlesex holiday rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$219 AUD$226 AUD$212 AUD$187 AUD$189 AUD$203 AUD$218 AUD$198 AUD$219 AUD$226 AUD$189 AUD$226 AUD
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 house rentals in Middlesex have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middlesex have wifi?

    Absolutely! We offer over 30 apartment 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 30 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 $57 AUD per night before taxes and fees

  • Verified guest reviews

    Over 14,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Middlesex holiday 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!

  1. Airbnb
  2. United States
  3. Vermont
  4. Washington County
  5. Middlesex