Holiday houses in Middlesex

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Top-rated holiday rentals in Middlesex

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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.

Guest favourite
The inviting living area includes a spacious couch and a coffee table with a chessboard set up. Natural light filters in through three large windows, enhancing the room's brightness. A dining table is visible in the background, alongside the kitchen area.
Apartment in Waterbury Village Historic District
4.97 out of 5 average rating, 99 reviews

Skiing, Winter Fun, Craft Beer, Electric Fireplace

Waterbury, Vt.: The best little foodie town in New England says The Boston Globe 5.10.2024 At Vermont’s crossroads, in the heart of the Green Mountains, you will be a short drive to great food, drinks, mountains, biking, hiking, swimming, river kayaking, Waterbury Resevior, and Vermont’s capital. Located over the garage of owner with a private entrance. Stairs are required to access property. 3 mins to downtown Waterbury 15 mins to Montpelier 30 mins to Stowe, Waitsfield, or Burlington

Guest favourite
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, 198 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 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 small vase containing vibrant flowers is placed on a wooden shelf. Sunlight filters through large windows, illuminating a loft area with a wooden ceiling. Spacious seating areas are visible below, providing a welcoming atmosphere.
Barn in Westford
5 out of 5 average rating, 283 reviews

The Book Barn: Newly Renovated Guesthouse

Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

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!

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
A lakeside home is nestled among lush trees on the shore of Lake Iroquois. The structure features a sloped roof and large windows, providing serene views of the water. A small dock is visible, along with kayaks positioned nearby under the green foliage.
Cottage in Hinesburg
4.98 out of 5 average rating, 201 reviews

Gorgeous lakefront home close to Burlington!

Lovely lakeside home w/expansive views of Lake Iroquois! Beautifully furnished 2 bedroom, 1.5 bath home with high-end finishes, hardwood, and slate floors. Relaxing great room, full kitchen, dining room, one-bedroom, and 1/2 bath on the first level. The entire upper level is devoted to a bedroom suite and features its own balcony, an oversized bathroom with a tiled shower, and a soaking tub. 2 kayaks and a canoe are available to explore the lake! 20 min. to Burlington.

Top Guest favourite
A bright living area is equipped with two blue velvet chairs positioned near a natural wood coffee table. Light enters through large windows, creating a warm ambiance. A rug with a geometric pattern covers the floor, complementing the overall modern bohemian decor.
Apartment in Montpelier
4.91 out of 5 average rating, 192 reviews

The Studio - in the heart of Montpelier

Welcome to The Studio in downtown Montpelier. This second floor unit is a cozy one bedroom with all you need for your stay. This charming renovated historic building is now an eclectic artful space with a separate bedroom, living room and kitchen/dining area. Walk to everything from here! One block to city center and all the downtown restaurants and shops. One off street parking space available. The perfect central location for exploring the surrounding areas.

Top Guest favourite
A cozy sitting area is seen with a green chair and a gray sofa positioned across from each other on a wooden floor. A round table sits between them, accompanied by a small black side table. A TV is mounted on the wall, and a door with a simple design is visible in the background.
Guest suite in Moretown
4.97 out of 5 average rating, 152 reviews

The Nest Studio

Off a quiet dirt road set up in the mountains, The Nest Studio is a bright and cozy space. Great for couples, the studio has a queen bed with an additional small twin pull out sofa, best for a little one. The newly remodeled Moretown studio is close to skiing, mountain biking, hiking and several wedding venues. Coffee and tea is provided. The Nest has a full kitchen, washer, dryer, and tiled shower. Secure bike storage and bike wash are present on the property

Top Guest favourite
Cabin in Worcester
4.95 out of 5 average rating, 231 reviews

Pet Friendly Cozy Treetop Cabin near Mt Worcester

Come get Vermonty like a local. A quiet sanctuary home base for adventure. Pick raspberries, climb a mountain, and cool off in a swimming hole. Far away from it all yet close to all you want to do. Wake up to a tree top sunrise. Have coffee in the hammock while watching the birds. Spend your days skiing fresh powder or apple picking and return home to quirky records, books, and games. Well-behaved pets welcome. Extensive seasonal local guide upon booking.

Top Guest favourite
A round, metal table surrounded by four matching chairs is positioned on a wooden deck overlooking the calm waters of Lake Champlain. Soft waves reflect the muted colors of the overcast sky, creating a serene atmosphere. The deck's railing frames the picturesque view.
Cottage in Swanton
4.97 out of 5 average rating, 128 reviews

Bluebird Cottage on Lake Champlain

Bluebird Cottage is located on the St Albans/Swanton town line directly on Lake Champlain on beautiful Maquam Shore. Enjoy our extensive private beach, sunsets from the large deck, shady lake breezes from the patios, large yard for outdoor activities and games complete with fire pit. Close by is the Missisquoi Wildlife Refuge, Alburg Dunes State Park, ski resorts, Burlington for fine dining and nightlife, the famous Lake Champlain Islands, and Canada.

Popular amenities for Middlesex holiday rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$221 AUD$228 AUD$214 AUD$188 AUD$191 AUD$206 AUD$220 AUD$200 AUD$221 AUD$228 AUD$191 AUD$228 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!

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