House holiday rentals in Middlesex

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Top-rated house rentals in Middlesex

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

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Top guest favourite
A bright living room features large windows, allowing natural light to fill the space. Two comfortable white sofas are positioned around a wooden coffee table, complemented by a patterned area rug. Exposed beams add a rustic charm to the wooden flooring.
Home in Waterbury Center
4.99 out of 5 average rating, 134 reviews

Cozy Farmhouse Nestled Between Stowe and Waterbury

Beautifully restored 1840's era farmhouse is the ideal retreat for ski vacations, hiking, biking & exploring lakes and streams, hanging with friends & family and work from home & homeschooling stays. Features post & beam construction, wide plank flooring, luxurious radiant heat, stainless steel appliances, large windows and powerful WiFi. Clean, cozy, and loads of character combining the best of old and new. Pls msg w/a few trip/group details before instant booking as we are on multiple sites!

Top guest favourite
The farmhouse is displayed with a classic white exterior and a metal roof. A welcoming front porch is flanked by steps leading up to the entrance. Surrounding fields stretch into the distance beneath a clear blue sky, showcasing the home's peaceful rural setting.
Home in East Montpelier
5 out of 5 average rating, 102 reviews

The 1919 Mountain Farmhouse, new hot tub and patio

Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

Top guest favourite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 539 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Top guest favourite
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, 149 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 favourite
The spacious kitchen features wooden cabinets and countertops with an array of modern appliances, including a stainless steel refrigerator and oven. Pot racks hang from the ceiling, and a window provides natural light, enhancing the inviting atmosphere of the cooking area.
Home in Moretown
4.98 out of 5 average rating, 143 reviews

Charming VT Cabin: Ski Sugarbush|Stowe|Mad River

Located centrally to everything the Mad River Valley offers, this well-appointed cabin has all the comforts of home for your next Vermont getaway. An ideal place for anyone seeking outdoor activities or just some relaxation. Secluded in the trees yet a short drive to Sugarbush and Mad River Glen ski areas, mountain biking, and hiking. Fly fishing and swimming spots on the Mad River are nearby. Enjoy great options for casual and fine dining, or prepare meals in our chef’s kitchen! @mrvstays

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, 141 reviews

Peaceful setting with Mountain Views

Rent the entire house. Large primary bdrm w/ private bath and 2 bdrms that accommodate 4 people w/ a shared full bath, one bonus room with pull out couch. Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (available 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 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
4.98 out of 5 average rating, 180 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.

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, 198 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 hot tub emits steam under the soft glow of string lights, creating a relaxing ambiance. The wooden deck features outdoor seating, inviting guests to enjoy the night. The rustic home blends with the surrounding nature, offering a peaceful retreat.
Home in Waterbury Center
5 out of 5 average rating, 102 reviews

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub

Welcome to our cozy retreat nestled in the picturesque town of Waterbury, Vermont. This newly renovated spacious and modern home is perfect for families or groups looking for a comfortable and stylish retreat. With its prime location, you’ll have easy access to local attractions, outdoor activities, renowned craft beer scene, world-class skiing, hiking trails, and breathtaking Mountain View’s - making it an easy getaway choice for nature lovers and outdoor enthusiasts.

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, 193 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 warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.
Home in Rochester
4.97 out of 5 average rating, 216 reviews

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Top guest favourite
A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.
Home in Moretown
4.98 out of 5 average rating, 306 reviews

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Popular amenities for house rentals in Middlesex

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹24,851₹26,538₹21,479₹17,662₹17,307₹17,751₹19,970₹18,283₹19,171₹22,189₹18,195₹27,248
Avg. temp-6°C-5°C0°C8°C15°C20°C22°C21°C17°C10°C4°C-2°C

Quick stats about house rentals in Middlesex

  • Total holiday rentals

    Explore 70 holiday rentals in Middlesex

  • Nightly prices starting at

    Middlesex holiday rentals start at ₹5,325 per night before taxes and fees

  • Verified guest reviews

    Over 5,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 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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