Vacation rentals in Middlesex

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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 R 637 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 14,400 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!

Top-rated vacation rentals in Middlesex

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

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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, 254 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
Cabin in Morristown
5.0 out of 5 average rating, 299 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.

Guest favorite
A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.
Treehouse in Newport
4.97 out of 5 average rating, 333 reviews

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

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
4.97 out of 5 average rating, 244 reviews

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.

Top guest favorite
A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.
Treehouse in Moretown
4.97 out of 5 average rating, 201 reviews

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

Top guest favorite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 180 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top guest favorite
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, 198 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 favorite
Home in Waterbury
4.98 out of 5 average rating, 100 reviews

Perry Pond House

Come with your family, friends or by yourselves to enjoy a restful stay at our newly built secluded hillside home. Perry Pond is located close to many recreation opportunities (ski, bike, hike, swimming holes, paddling), restaurants, breweries, and scenic attractions in the Waterbury-Stowe-Waitsfield-Montpelier area. Its private setting overlooking a pond and distant views provides the perfect getaway for those seeking a peaceful break from their daily routine or to relocate remote work.

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
4.95 out of 5 average rating, 208 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 favorite
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
4.98 out of 5 average rating, 367 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 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
4.94 out of 5 average rating, 193 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, 199 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.

Popular amenities for Middlesex vacation rentals

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 2,644 ZARR 2,708 ZARR 2,437 ZARR 2,293 ZARR 2,469 ZARR 2,469 ZARR 2,453 ZARR 2,230 ZARR 2,469 ZARR 2,548 ZARR 2,134 ZARR 2,548 ZAR
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 house rentals in Middlesex?

    Experience the best of Middlesex with our house rentals, starting at about $60 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 apartment rentals in Middlesex have air conditioning?

    Absolutely! We offer over 20 apartment 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 20 apartment 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 house rentals in Middlesex have free parking?

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