
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.

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.

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.

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 | Mad River
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.

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 — Perfect for Ski Weekend!
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

Sunset Treehouse

Wildewood: Modern | Fireplace | Luxe in Stowe

Sylvan Hideaway - Lower Village - Game Room

SugarBear- Pool, Hot Tub, 2 En Suites BR

Stoweaway

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

Perry Pond House

Mid century modern gem with views of Sugarbush

Waterfall Oasis with Large Deck

Charming and Centrally Located Waitsfield Home.

Year-round mountain escape, stunning views!

Convenient Retreat
Private house rentals

Waterbury Village Escape - Entire 3BR/2BA House

Perfect Vermont Escape | Cozy & Centrally Located

Charming Farmhouse near Maple Corners

Secluded Winter Paradise with Hot Tub

Huge Waterbury home near Stowe with views/sauna

Cozy VT Getaway - Fully Furnished for Longer Stays

Stowe Log Cabin! Close to town!

Lakewood Bungalow & Sauna
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $466 NZD | $497 NZD | $403 NZD | $331 NZD | $324 NZD | $333 NZD | $374 NZD | $343 NZD | $359 NZD | $378 NZD | $333 NZD | $398 NZD |
| 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 $100 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Middlesex holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- ECHO, Leahy Center for Lake Champlain
- Pump House Indoor Waterpark
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- University of Vermont
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- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Waterfront Park
- Middlebury College




