
House vacation 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.

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.

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.

Modern Barn Perched on 24 Acres w/ Stunning Views
Relax and recharge at this bucolic 24 acre retreat perched up on a stunning country road. With expansive 180 degree views of Mt Mansfield (Stowe ski resort), your own trails to explore, and great hiking/XC trails nearby, The Lookout is a truly special spot for a romantic or low key getaway in the mountains. Feel away from it all, with tons to explore out your back door, while having modern amenities in a renovated, beautifully designed barn < 15 min to Stowe Village and 10 min to Morrisville.

Vermont 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

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.

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.

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.

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.

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.

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!

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!

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 Middlesex house rentals
House rentals with a pool

Sunset Treehouse

Mountain View Farmhouse w/ Orchard White Christmas

Epic Views of the Green Mountains

Sylvan Hideaway - Lower Village - Game Room

Winter Wonderful Waitsfield Spacious VT Home w/Spa

Charming Sugarbush Standalone Condo

Gorgeous mtn forest retreat 3 mins from ski resort

EPIC Stowe Getaway - Great For Families & Friends
Weekly house rentals

Modern Design Retreat: Sauna + Views Near Stowe

The Vermont Red Barn

Sky Zen - Ridgeline Retreat

Cozy VT Getaway - Fully Furnished for Longer Stays

Perry Pond House

Lakewood Bungalow & Sauna

Waterfall Oasis with Large Deck

Charming and Centrally Located Waitsfield Home.
Private house rentals

Peaceful Home with Gorgeous Views

Elegant 1-Bedroom Home in Stunning Location

A Magical Mountainside Farm: Your Personal Narnia

XC-Ski Heaven, Modern Secluded Cabin in Greensboro

Charming Farmhouse near Maple Corners

VT Views White Mtn Stay Hot Tub Fire Pit Pool Tble

Secluded, Winter Paradise with Hot Tub

Spruce Mountain View House
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,028 | ﺩ.ﺇ1,098 | ﺩ.ﺇ889 | ﺩ.ﺇ731 | ﺩ.ﺇ716 | ﺩ.ﺇ735 | ﺩ.ﺇ826 | ﺩ.ﺇ757 | ﺩ.ﺇ793 | ﺩ.ﺇ918 | ﺩ.ﺇ753 | ﺩ.ﺇ1,127 |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Quick stats about house rentals in Middlesex

Total vacation rentals
Explore 70 vacation rentals in Middlesex

Nightly prices starting at
Middlesex vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 5,840 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 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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- Sugarbush Resort
- Jay Peak Resort
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