House holiday rentals in Middlesex

4.93 out of 5 average rating, 344 reviews

The exterior of a wooden house is displayed, featuring a sloping entrance with a wooden walkway leading to the main entry. Large windows provide views of the lake and surrounding greenery, while colorful flower beds enhance the peaceful setting.

Home in Port Kent

18 Lake Stunning View of Champlain in Adirondacks

Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY, this gem is the perfect place to relax and get away. People come from all across the country to tour this charming area on bicycles in summer, and from all over the world during the winter for Lake Placid's winter sports. In fall, the colors are vibrant and breathtaking. Fresh maple products are on tap in Spring. Enjoy area attractions such as Ausable Chasm, High Falls Gorge, Port Kent Beach, golf, orchards, hiking and biking.

A spacious living area showcases vaulted ceilings with exposed wooden beams. A dark sectional sofa is positioned near a modern coffee table, facing large glass doors that open to a forested view. A sleek kitchen features stainless steel appliances and a wood-burning stove adds warmth.

4.92 out of 5 average rating, 118 reviews

Brand new Beautiful Modern Clean Home On River

Kick back and relax in this calm, stylish space, nestled in the woods of Stowe. This gorgeous new two bedroom , two bath, is located right on the river. A beautiful, indoor, outdoor living space with ample room to spread out & enjoy a cup of coffee on the deck. This is a sleek, clean new build that is minutes to Main Street Stowe, two miles to Trapp Family Lodge and 15 minutes to Stowe Mountain Resort. You will never want to leave when you experience nature at its finest in this stunning space.

4.96 out of 5 average rating, 534 reviews

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

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.

An exterior view of a contemporary home features large windows allowing natural light in. A spacious deck is adorned with a dining set, shaded by a dark umbrella. Lush greenery surrounds the property, offering a serene atmosphere.

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.

4.98 out of 5 average rating, 139 reviews

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

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

4.98 out of 5 average rating, 175 reviews

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

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.

4.96 out of 5 average rating, 196 reviews

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

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.

An open living space features wooden beams overhead and large windows that allow natural light. A cozy seating area with leather chairs and a coffee table is situated beside a modern kitchen, equipped with stainless steel appliances and a dining table with stools.

4.96 out of 5 average rating, 115 reviews

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe

At this quiet 2BR on five green acres, you’ll start your mornings with coffee by the pond and end your days by the fire. Bring your bikes to ride over to Cady Hill, snow shoe or hike in Smuggler’s Notch, or stroll the flat mile into town for dinner. Inside, you’ll find toxin-free cookware, natural fiber bedding, and crisp spring-fed water straight from the tap. With a bunk room for the kids and a king suite for you, it’s a calm, well-kept base for year-round adventure in Stowe.

4.92 out of 5 average rating, 221 reviews

A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.

Home in Roxbury

Captain Tom's Cabin - Secluded Vermont Getaway

Welcome to Capt. Tom's Cabin. Nestled in the hills of Vermont with a beautiful view of the Green Mts., this 2-storey, 2 bedroom log house on 44 acres offers seclusion, serenity and privacy. Two large bathrooms, full kitchen, central heat, gas fireplace, pond and deck. Great for winter sports enthusiasts and nature lovers. Good wifi, dog-friendly with a fee. Please google and read Vermont's covid restrictions and agree to adhere to them before making a reservation.

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.

4.94 out of 5 average rating, 192 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.

A comfortable living area features two dark sofas arranged around a central coffee table on a textured area rug. A lamp stands beside one sofa, and a stone fireplace adds warmth to the space. Large windows allow natural light to illuminate the room.

4.97 out of 5 average rating, 208 reviews

Vermont Getaway Home - Perfect Location

Central Location! Covered patio with propane fire table. Cozy 2 bed, 1.5 bath home, in a 2 unit duplex, 1200 sq.ft. Fully furnished. Whether you choose to stay in or want to get out, this is a great location! 13 mi. to Stowe Mtn., 21 to Sugarbush, 25 to Burlington, 3 to local hiking trails, and 4 to downtown Waterbury, enjoy local restaurants, craft beer, and more! Bedrooms and full bath are on 2nd floor. AC throughout the house! Smoke Free, Pet Free Rental.

4.97 out of 5 average rating, 215 reviews

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

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!

Popular amenities for Middlesex house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

4.89 out of 5 average rating, 226 reviews

Luxury Condo Tucked in the Heart of Killington

Superhost

A white farmhouse is set against a clear blue sky, surrounded by lush greenery and large trees. A private pool reflects the house and trees, creating a serene outdoor space. A rustic barn can be seen in the background, indicating the property's charm.

Home in Plainfield

4.83 out of 5 average rating, 127 reviews

Mountain View Farmhouse w/ Orchard White Christmas

4.88 out of 5 average rating, 260 reviews

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

4.99 out of 5 average rating, 146 reviews

A spacious living room is illuminated by large windows overlooking the forest. A leather sofa and armchair are arranged around a patterned area rug. A coffee table and side table with modern lamps complete the cozy seating area. A wood-burning fireplace adds warmth to the setting.

Home in Killington

SugarBear- Pool, Hot Tub, 2 En Suites BR

A spacious living area features modern furnishings, including a light gray sofa and a rustic wooden coffee table. Large windows allow natural light to fill the space, with greenery visible outside. A dining area is positioned nearby, complemented by a contemporary light fixture.

4.93 out of 5 average rating, 30 reviews

Surrounded by nature perfect for fall!

4.96 out of 5 average rating, 25 reviews

An outdoor seating area features modern chairs and a small table, overlooking rolling hills and mountains in the distance. The framework highlights a tranquil setting with expansive views of the landscape, inviting relaxation and enjoyment of the natural surroundings.

Home in Morristown

The Vista - 180º Mt. views w/Pool 12min to Stowe

Superhost

A modern stand-alone condo is set against a backdrop of vibrant autumn foliage. The light gray exterior features large windows, allowing natural light to fill the interior. A wooden deck and stairs lead to the entrance, surrounded by well-maintained landscaping.

Home in Warren

4.82 out of 5 average rating, 119 reviews

Charming Sugarbush Standalone Condo

A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.

4.98 out of 5 average rating, 285 reviews

EPIC Stowe Getaway - Great For Families & Friends

Weekly house rentals

5 out of 5 average rating, 61 reviews

The exterior of a modern black house is shown, featuring a sloped metal roof and solar panels. Large floor-to-ceiling windows allow natural light to fill the interior, with a spacious deck extending in front. Lush greenery surrounds the structure, emphasizing its connection to nature.

Home in Waterbury

Modern Dwell Home +Sauna between Stowe/Waterbury

An aerial view captures a secluded home surrounded by vibrant autumn foliage. The cozy structure with a green roof is set amidst an array of trees displaying rich reds, oranges, and yellows, highlighting the beauty of the natural landscape.

4.9 out of 5 average rating, 77 reviews

The Vermont Red Barn

Home in Waterbury Village Historic District

The exterior of a newly built hillside home is shown, featuring a wooden facade with a sloped roof. Surrounded by tall trees, the structure includes large windows and a garage attached to the side. A clear pathway leads to the entrance amidst a snowy landscape.

4.97 out of 5 average rating, 74 reviews

Perry Pond House

5 out of 5 average rating, 17 reviews

A grassy outdoor area is bordered by natural landscaping, featuring a picnic table and several seating options arranged for relaxation. Lush greenery and rolling hills create a tranquil backdrop under a bright blue sky filled with scattered clouds.

Home in Worcester

Spacious and Secluded Family Home

A cozy living area features a sectional sofa adorned with yellow accent pillows and a stylish decorative throw. A round coffee table with a metallic base sits centrally, accompanied by a mid-century armchair. The space is brightened by natural light flowing in from multiple windows.

4.86 out of 5 average rating, 186 reviews

Modern design in the woods, private, beautiful

A modern Adirondack style home is set on a lush green lawn dotted with yellow flowers. A spacious deck wraps around the exterior, providing access to the natural surroundings. Towering trees create a serene backdrop, completing the inviting scene of outdoor living.

4.81 out of 5 average rating, 32 reviews

Year-round mountain escape, stunning views!

A charming family home is displayed with a green exterior and white columns. Warm light spills from the windows, hinting at a cozy interior. The surrounding yard features a well-maintained lawn, with a porch that includes seating options, inviting relaxation in a tranquil setting.

4.95 out of 5 average rating, 22 reviews

Convenient Retreat

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.

4.96 out of 5 average rating, 140 reviews

Peaceful setting with Mountain Views

Private house rentals

The living room features a comfortable gray sofa paired with two vibrant orange chairs, arranged around a circular coffee table. A blend of natural light and soft overhead lighting enhances the inviting space. A rustic kitchen is visible in the background, with modern appliances and decor.

4.96 out of 5 average rating, 90 reviews

The Stowey Deer | King Bed | 15 Min to Skiing

An aerial view of a spacious mountain house set on a green expanse, surrounded by vibrant autumn foliage. The structure features large windows and a multi-car driveway, with hills visible in the background under a clear blue sky.

4.88 out of 5 average rating, 58 reviews

Huge Waterbury home near Stowe with views/sauna

5 out of 5 average rating, 26 reviews

An aerial view showcases a classic farmhouse surrounded by lush greenery and colorful fall foliage. The expansive property spans 66 acres, featuring well-maintained gardens and scenic mountain views in the background. The peaceful landscape invites exploration and relaxation.

Home in Duxbury

Secluded, Magical Paradise with Hot Tub

4.93 out of 5 average rating, 14 reviews

Home in Williamstown

Cozy VT Getaway - Fully Furnished for Longer Stays

4.93 out of 5 average rating, 95 reviews

A cozy living area is arranged with two beige sofas positioned around a wooden coffee table. A small television is placed on a stand, and large windows allow natural light to fill the space. A patterned rug adds warmth to the floor.

Home in Moretown

Cozy net zero apartment

5 out of 5 average rating, 10 reviews

Home in Woodbury

Lakewood Bungalow

Home in Waterbury Village Historic District

A charming post and beam house is shown from an elevated perspective, highlighting the wrap-around deck and lush, landscaped yard. The private waterfall can be seen alongside the structure, offering a natural focal point in the surroundings.

4.95 out of 5 average rating, 59 reviews

Waterfall Oasis with Large Deck