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
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, 154 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
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 charming backyard scene showcases a tiny home with a wooden exterior adjacent to a classic white house. Lush green grass surrounds the properties, enhanced by vibrant flowers, including tall sunflowers. Dense trees form a tranquil backdrop, completing this inviting outdoor space.
Home in Montpelier
4.94 out of 5 average rating, 386 reviews

Modern not so tiny house

Our backyard tiny home is walking distance to historic downtown Montpelier. Located on a quiet street, its many windows highlight all the efficiencies of tiny house living, including a fully equipped kitchen, radiant floor heat and the option of woodstove coziness. The bathroom includes a spacious walk-in shower and modern concrete sink. Two small bedrooms share a featured rotating wall and sliding barn door. The design plan is clean lines, minimalist decor and efficient energy use.

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, 198 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.

Top 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, 201 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
4.99 out of 5 average rating, 118 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.

Superhost
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
4.92 out of 5 average rating, 100 reviews

Cozy net zero apartment

Cozy one bedroom apartment with all the modern conveniences to make this your home base for a weekend, a week, or longer. Apartment runs on entirely solar power, and is heated and air conditioned. 20 minutes from sugarbush/mad river and 10 minutes from Waitsfield. 1 mile to the moretown general store. A perfect home base for exploring the mountains. Use our heated and unfinished stairway for your muddy and snowy boots and gear storage. Separate entrance through our garage.

Top guest favourite
Home in Moretown
4.98 out of 5 average rating, 151 reviews

Secluded Ski Cabin w/ Chef’s Kitchen | Sugarbush

Discover a peaceful Vermont retreat in the heart of the Mad River Valley. Secluded in the woods, our well-appointed cabin offers a quiet escape within a scenic 25-minute drive to Sugarbush and Mad River Glen. It’s an ideal base for skiing, hiking, or fly fishing the nearby Mad River. After a day of adventure, enjoy local valley dining or cook a gourmet meal in our chef’s kitchen. Perfect for those seeking both outdoor thrills and total relaxation. Follow us at @mrvstays

Top guest favourite
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.
Home in Waterbury Center
4.97 out of 5 average rating, 215 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.

Top guest favourite
An open living area features a cozy leather sofa set near a circular rug, with wooden floors adding warmth. Several windows allow natural light to filter in, revealing the charming wooden ceiling and rustic decor, enhancing the inviting atmosphere of the space.
Home in Waitsfield
4.95 out of 5 average rating, 104 reviews

Elegant 1-Bedroom Home in Stunning Location

Situated one mile from downtown Waitsfield, you can take it easy at this unique and tranquil getaway with stunning views of Sugarbush and Mad River Glen ski areas. Enjoy the outdoor patio with firepit, quiet/private setting, nearby amenities (skiing, biking, golf, fishing, ...), shopping in downtown Waitsfield and Warren Village, and nearby acclaimed eateries. Or, best of all, curl up with a good book and enjoy the peacefulness of this beautiful and unique home.

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, 318 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!

Top guest favourite
The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.
Home in Starksboro
4.99 out of 5 average rating, 151 reviews

Forest Hideaway

Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.

Popular amenities for house rentals in Middlesex

When is the best time to visit Middlesex?

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Avg. price€ 236€ 252€ 204€ 168€ 164€ 168€ 189€ 173€ 182€ 191€ 168€ 201
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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 € 51 per night before taxes and fees

  • Verified guest reviews

    Over 6,110 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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