
House vacation rentals in Middlesex
Find and book unique houses on Airbnb
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 6,380 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!
Top-rated house rentals in Middlesex
Guests agree: these houses are highly rated for location, cleanliness, and more.

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!

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.

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.

Peaceful setting with Mountain Views
Rent the entire house. Primary bdrm w/ private bath, 2 bdrms that accommodate 4 people w/ shared full bath, one bonus room w/ pull out couch and a 1/2 bath . Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (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!

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.

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.

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.

Secluded Mad River Valley Cabin: Chef’s Kitchen
Discover a peaceful Vermont retreat in the heart of the Mad River Valley. Secluded in the pines, 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

Full House 3 Bedrooms/3.5 Baths
Come to the area for outdoor adventures, business needs or romantic retreats and you will enjoy all the beauty Vermont has to offer. All accommodations are close (delicious restaurants, award winning craft beer breweries, small locally owned shops, miles of mountain biking/hiking/skiing/snowboarding and a huge arts & culture scene giving you plenty of ways to fill your days. Near Bolton, Mad River Glen, STOWE and Sugarbush are a short scenic drive away.
Popular amenities for Middlesex house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Vermont Mountain Summer Retreat

Steps to Golf and Mountain Biking

Mountain View Farmhouse w/ Orchard, Pool is Open!

Ranch at Mendon Mt Orchards

SugarBear- Pool, AC, Sauna, Gym, Tennis!

Charming Sugarbush Standalone Condo

Private 3 Acre Forest Retreat | Trails Pool Fire
Weekly house rentals

Sky Zen - Ridgeline Retreat

The Looking Glass, a modernistic escape

Perry Pond House

Lakewood Bungalow & Sauna

Cozy VT Mountain House for Skiers, Hikers & Bikers

Waterfall Oasis with Large Deck

Year-round mountain escape, stunning views!

Convenient Retreat
Private house rentals

Secluded Paradise in Greensboro on Barr Hill

Charming Farmhouse near Maple Corners

Peaceful Meadow Retreat • Cobbler Hill Farm Stay

Huge Waterbury home near Stowe with views/sauna

The Gambrel Mountain Retreat at Twin Ponds

On the River Aframe. Cozy River Lake & Mtn Retreat

Stowe Modern Masterpiece with Gym!

Sunset facing valley view home - Waterbury Stowe
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ936 | ﺩ.ﺇ1,072 | ﺩ.ﺇ823 | ﺩ.ﺇ731 | ﺩ.ﺇ716 | ﺩ.ﺇ735 | ﺩ.ﺇ826 | ﺩ.ﺇ757 | ﺩ.ﺇ793 | ﺩ.ﺇ834 | ﺩ.ﺇ735 | ﺩ.ﺇ878 |
| 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 |
Destinations to explore
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- Rentals with a fire pit Middlesex
- Rentals with a fireplace Middlesex
- Rentals with outdoor seating Middlesex
- Rentals with a patio Middlesex
- Family-friendly rentals Middlesex
- Apartment rentals Middlesex
- Pet-friendly rentals Middlesex
- Rentals with a washer and dryer Middlesex
- House rentals Washington County
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- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Stowe Mountain Resort
- Smugglers' Notch Resort
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- Jay Peak
- Jay Peak Resort Golf Course
- Dartmouth College
- Middlebury College
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Montshire Museum of Science
- Pump House Indoor Waterpark
- Spruce Peak
- Warren Falls
- Elmore State Park
- Shelburne Museum
- Snow Farm Vineyard & Winery
- Quechee Gorge
- Shelburne Vineyard





