
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 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.

CLASSIC VT STYLE
This is an authentic VT house tucked between two of the state's most celebrated ski resorts, Stowe and Smuggler's Notch. We are about 30 minutes north of Mount Mansfield with tons of hiking and exploration opportunities. In this area you can enjoy some of the state's most popular outdoor recreational attractions and activities. The space is private and serene and works for all different kinds of local adventures in any season. Come experience a unique part of VT in your own unique VT home!

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!

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.

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.

Private 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

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.

Spacious Eco-Friendly Stowe Home for Family Fun
Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

Cozy Hideaway w Hot Tub — Bike, Hike, Play & Relax
Welcome to our lovely 1865 Waterbury Village Hideaway. We are located 1/2 mile from the very best Mountain Biking trails, less than 1 mile to great food and beer, access to more than 7 Ski Resorts, including Stowe, Sugarbush & Killington, and 30 minutes from Burlington and the Waterfront. Use this Hideaway to take advantage of everything Vermont has to offer and relax in the soothing waters of our Hot Tub at the end of the day.
Popular amenities for Middlesex house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Last Run Stowe: Pool, spacious, 5min to Village

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
Weekly house rentals

Modern Design Retreat: Sauna + Views Near Stowe

Cheerful, Cozy, Quiet Home near Montpelier, VT

Sky Zen - Ridgeline Retreat

Charming Farmhouse near Maple Corners

Bear Creek | Mountain & Forest Views + Bbq

Cozy VT Mountain House for Skiers, Hikers & Bikers

Waterfall Oasis with Large Deck

Charming and Centrally Located Waitsfield Home.
Private house rentals

Lakeside Vermont Retreat

Secluded Paradise in Greensboro on Barr Hill

The Looking Glass, a modernistic escape

Huge Waterbury home near Stowe with views/sauna

The Gambrel Mountain Retreat at Twin Ponds

Lakewood Bungalow & Sauna

Cozy home with mountain views

Sunsets on the Ridge, Group Friendly
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $356 CAD | $407 CAD | $313 CAD | $278 CAD | $272 CAD | $279 CAD | $314 CAD | $287 CAD | $301 CAD | $317 CAD | $279 CAD | $334 CAD |
| 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 $84 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Middlesex vacation 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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- Jay Peak Resort
- Sugarbush Resort
- Pico Mountain Ski Resort
- Stowe Mountain Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Killington Resort
- Dartmouth College
- Middlebury College
- Jay Peak
- ECHO, Leahy Center for Lake Champlain
- Montshire Museum of Science
- University of Vermont
- Pump House Indoor Waterpark
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Warren Falls
- Elmore State Park
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Waterfront Park





