Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Top guest favorite
A charming barn-style structure is shown with a spacious driveway leading up to its entrance. The architecture features a peaked roof and wood paneling, complemented by the neatly arranged firewood at the side. Lush green grass surrounds the entryway, inviting exploration.
Farm stay in Berlin
4.96 out of 5 average rating, 297 reviews

Farm Stay - Working livestock farm

Come stay in our apartment connected to the barn on our active working farm. We are located 3 miles from the state capitol building in Montpelier, but you would never know it up here. You can cross country ski, snowshoe, hike, or bike out your front door, and we are located within 45 min. from Sugarbush, Stowe, Mad River Glen, & Bolton Valley. You can also check out the local beer & spirits scene, or just relax at the farm. Guests are always welcome to tour the grounds and see the animals.

Top guest favorite
A spacious home is set against a mountainous backdrop, featuring large windows and a wraparound porch. The well-maintained lawn leads up to the house, while a small red structure is visible in the distance, providing a charming contrast to the green landscape.
Apartment in Waterbury Center
4.98 out of 5 average rating, 181 reviews

1 Bedroom apartment. Between Stowe and Waterbury.

This one bedroom apartment is in a quiet residential neighborhood nestled at the foot of Hunger Mtn. Private entryway, over garage of homeowner. Queen bed and pull out (queen) couch, with full kitchen, and laundry. Expansive views of the mountains. 10-15 minutes to Stowe village, 10 minutes to Waterbury. In the heart of the mountains, this cozy apartment is steps away from mountain biking and hiking, and within a short driving distance of several major ski resorts. No added cleaning Fees

Top guest favorite
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 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
4.99 out of 5 average rating, 158 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.

Top guest favorite
Treehouse in Moretown
4.99 out of 5 average rating, 134 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

Insulated, thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Fabulous “Jotul” fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
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 favorite
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, 300 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*

Top guest favorite
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.

Popular amenities for Middlesex vacation rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ569ﺩ.ﺇ588ﺩ.ﺇ551ﺩ.ﺇ485ﺩ.ﺇ492ﺩ.ﺇ529ﺩ.ﺇ566ﺩ.ﺇ514ﺩ.ﺇ569ﺩ.ﺇ588ﺩ.ﺇ492ﺩ.ﺇ588
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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 vacation rentals in Middlesex

  • Total vacation rentals

    Explore 140 vacation rentals in Middlesex

  • Nightly prices starting at

    Middlesex vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 14,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 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!

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