
Holiday houses in Middlesex
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Top-rated holiday rentals in Middlesex
Guests agree: these stays are highly rated for location, cleanliness and more.

Farm Stay - Working livestock farm
Come stay in our apartment connected to the barn on our active working farm. We are located 3 miles from the state capitol building in Montpelier, but you would never know it up here. You can cross country ski, snowshoe, hike, or bike out your front door, and we are located within 45 min. from Sugarbush, Stowe, Mad River Glen, & Bolton Valley. You can also check out the local beer & spirits scene, or just relax at the farm. Guests are always welcome to tour the grounds and see the animals.

Jules Gem
Reconditioned Barn Apartment. One large room with 4 large windows creating much natural light with kitchenette, no oven at this time, but there is a toaster oven & BBQ Grill for your use Overlooking Mountains and situated next to a river. Enjoy the sounds and views of country on this 90 acre property. All new amenities and full bath with shower. Private swimming hole on property, steps from sought after hiking, 12 minutes to downtown Montpelier with fine dining, bars and unique shopping.

200 acre Stowe area Bunkhouse.
Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

the little house
Come rejuvenate in our sweet little cabin tucked into the Vermont mountains. It has such wonderful healing energy! ✨ Cozy up to read a book next to the fireplace or book a private healing session at my studio in Montpelier, VT. I have a passion for creating welcoming, safe spaces that support your nervous system & empower your soul. ❤️ -On site Minister Brook access--5 min. walk -Lots of skiing, hiking, water to explore -18 min to Montpelier- funky downtown, eccentric shops & restaurants

4-Season Treehouse @ Bliss Ridge; Best Views in VT
thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Farmhouse with Sunset Mountain Views
Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, 18 minutes to Stowe, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

Waterbury Center Guest Bedroom - 244 Howard
The guestroom room has a separate entrance located off a covered, back porch with a small table and chairs for summer use. There is adjustable heat and cool air from the wall mounted air-source, heat pump. The little kitchen alcove is convenient for coffee or tea or a light meal (toaster oven, single induction “hot” plate, water heater) We live in a historic building. Our neighborhood is very close to Rte 100. Waterbury village and Stowe are nearby too with skiing, hiking and biking.

A true Vermont get-away cabin in the woods
Badger Cottage offers a true rustic Vermont experience nestled in the woods with spectacular views and a quiet and peaceful ambiance. Once a barn, carefully reconstructed on the owners’ property, and modernized to today’s standards, this post and beam cabin is warm and cosy in winter and cool in summer. Well behaved dogs are very welcome and will enjoy the walks in the woods. Covid vaccinations are required. The owners live in an adjacent house with their very friendly Border Terrier

Contemporary Studio in Montpelier
Keep it simple at this peaceful and centrally-located place just minutes from downtown Montpelier. A contemporary studio set within the charm of a historical building. Relax under the apple tree with your morning coffee or take a five minute walk into town for freshly-baked pastries. Discover what our vibrant little city has to offer without ever getting into your car. No matter the season, there are great places nearby to explore for swimming, hiking, biking, and skiing.

The Roost - Recharge & Relax
Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.

Meadow Woods Cabin, private, cozy and unconnected
Enjoy beautiful sunsets from your rocking chair on the cabin's wonderful porch. There is a large, well equipped kitchen, open space floor plan, new shower unit and plenty of closet space in the bedroom. Easy access to VAST snowmobile trails, within an hour's drive to 3 ski areas (Stowe, Smuggler's Notch and Jay Peak), X-Country skiing right outside the door or in Craftsbury or Stowe. Elmore State Park is 3 miles away. Hiking trails and kayaking abound!

B suite Zenbarn 2BR Apt | VIP Perks Live Music
Zenbarn Loft: A Cozy 2-Bedroom Retreat Above Vermont’s Iconic Music Venue 🎶⛰️🍻 Stay in the heart of Vermont, just minutes from Stowe, Waterbury, and top breweries like Alchemist and Lawson’s! This 2-bedroom suite offers a cozy retreat with a kitchenette, fast WiFi, and a private entrance (shared hallway). Live music below creates a vibrant atmosphere. Please message us before booking with any questions to ensure this is the perfect stay for you!
Popular amenities for Middlesex holiday rentals
Stay near Middlesex's top sights
Other great holiday rentals in Middlesex

Countryside Cottage with Sauna and Fireplace

Sky Zen - Ridgeline Retreat

Perry Pond House

Spacious country retreat close to town and nature!

Farmhouse Sunset Studio at Anderbell Acres

Waterfall Oasis with Large Deck

Morningstar Meadow - your home in Vermont

The Carriage House
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $232 AUD | $239 AUD | $224 AUD | $197 AUD | $200 AUD | $215 AUD | $230 AUD | $209 AUD | $232 AUD | $224 AUD | $194 AUD | $221 AUD |
| 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Middlesex?
Four-legged friends are welcome in Middlesex. Choose from more than 30 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Middlesex?
Experience the best of Middlesex with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Middlesex have free parking?
Absolutely! We offer over 30 apartment rentals with free parking in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middlesex have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Middlesex?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with free parking, over 60 homes with a kitchen, over 40 homes with air conditioning, over 70 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Middlesex have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middlesex have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Middlesex?
Yes! Work meets play with ease at over 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.
Quick stats about holiday rentals in Middlesex

Total holiday rentals
Explore 140 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at $75 AUD per night before taxes and fees

Verified guest reviews
Over 13,730 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
140 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!
Destinations to explore
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- Sugarbush Resort
- Jay Peak Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Dartmouth Skiway
- Jay Peak Resort Golf Course
- Lucky Bugger Vineyard & Winery
- Pump House Indoor Waterpark
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Montshire Museum of Science
- Ethan Allen Homestead Museum
- Burlington Country Club
- Mt. Eustis Ski Hill
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery




