
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.

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.

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!

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.

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.

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.

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

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.

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.

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 house rentals in Middlesex
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Sunset Treehouse

Wildewood: Modern | Fireplace | Luxe in Stowe

Sylvan Hideaway - Lower Village - Game Room

Ranch at Mendon Mt Orchards

SugarBear- Pool, Hot Tub, 2 En Suites BR

Charming Sugarbush Standalone Condo

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

Modern Design Retreat: Sauna + Views Near Stowe

The Vermont Red Barn

Perfect Vermont Escape | Cozy & Centrally Located

Cozy VT Getaway - Fully Furnished for Longer Stays

Perry Pond House

Charming and Centrally Located Waitsfield Home.

Year-round mountain escape, stunning views!

Convenient Retreat
Private house rentals

The Old Schoolhouse

Sky Zen - Ridgeline Retreat

Charming Farmhouse near Maple Corners

Snowy Meadow Getaway—Ski Smugglers, Stowe, JayPeak

Lakewood Bungalow & Sauna

Waterfall Oasis with Large Deck

Cozy home with mountain views

On the River Aframe. Cozy River Lake & Mtn Retreat
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 236 | € 252 | € 204 | € 168 | € 164 | € 168 | € 189 | € 173 | € 182 | € 191 | € 168 | € 201 |
| 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 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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- House rentals Washington County
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- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Jay Peak
- Bolton Valley Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- ECHO, Leahy Center for Lake Champlain
- Montshire Museum of Science
- Dartmouth College
- Stowe Mountain Resort
- Middlebury College
- University of Vermont
- Shelburne Museum
- Waterfront Park
- Kingdom Trails
- Shelburne Vineyard
- Lake Champlain Chocolates
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Warren Falls




