House holiday rentals in Middlesex

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Popular amenities for Middlesex house rentals

House rentals with a pool

Superhost
Home in Stowe
4.82 out of 5 average rating, 11 reviews

Modern condo at village green

DanRating, 5 stars2 months ago
Beautiful spot, and a quick walk to the bus stop if some of your family is taking too long to get ready!
Guest favourite
Home in Killington
4.91 out of 5 average rating, 204 reviews

Luxury Condo Tucked in the Heart of Killington

Anil KumarRating, 5 stars2 days ago
The place was amazing. Probably one of the best Airbnb’s I’ve rented in terms of value for money. Very responsive host. The location is private, had pretty much all the amenities one needs and everything was well organized. The only downside is the check in is at 3pm but the checkout is at 10am. Which is pretty much unheard of. I’ve asked for one hour extension but was immediately sent a 25$ surcharge request for 1 hour. Apart from that everything was good.
Top Guest favourite
Home in Mendon
4.89 out of 5 average rating, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars2 weeks ago
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!
Top Guest favourite
Home in Waitsfield
5 out of 5 average rating, 31 reviews

Winter Wonderful Waitsfield Spacious VT Home w/Spa

SeanRating, 5 stars6 months ago
Our stay in Sara and Mikes home in Waitsfield was incredible! Upon arrival into the mad river valley, the surrounding views were instantly beautiful and calming. The moment we stepped in the house we honestly felt right at home. The layout of the house is so calming and tasteful. Everything is perfectly organized, down to the labeling for all of the dishes and cookware so you’ll never have trouble finding what you need! Waking up and heading by downstairs for a workout in the home gym, followed by a dip in the hot tub on the secluded back deck was an insanely relaxing way to start the day. The custom built bed frames/furniture and the overall craftsmanship of the space added a comforting artistic value to the stay. Don’t get me started on the screen porch! This house is full of amenities and I’ve honestly never felt more at home at an air b&b stay. Nice quiet respectful neighborhood in an amazing community, would recommend this spot to anyone and we hope to return in the future!
Top Guest favourite
Home in Killington
4.99 out of 5 average rating, 134 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

JennRating, 5 stars5 days ago
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.
Top Guest favourite
Home in Barre
4.94 out of 5 average rating, 67 reviews

Charming Barre Getaway

AaronRating, 5 stars1 month ago
The best stay around! Barre is a great little walkable town with shops and restaurants to explore. It’s only a short drive to local ski / snowboarding mountains as well as some hiking. The house was clean, spacious and very nicely decorated. The kitchen had everything we needed that made it feel like we were cooking right at home, which we loved. Karen and Courtney were responsive and very helpful!
Superhost
Home in Warren
4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

PerryRating, 5 stars1 month ago
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!
Superhost
Home in Stowe
5 out of 5 average rating, 3 reviews

Cool Pool, a Private Oasis

MeganRating, 5 stars9 months ago
Lovely house and beautiful lot! Spent lots of time playing in the yard, swimming in the pool and exploring all the things that Stowe has to offer. We'll be back!

Weekly house rentals

Guest favourite
Home in Lincoln
4.98 out of 5 average rating, 205 reviews

Modern Home in Lincoln Sauna / Pond / Ev Chg / Pvt

CatherineRating, 5 stars1 month ago
Bjorn’s home is pristine and could not be nestled in a more beautiful place. He was very responsive and the house is well supplied with everything you could need. Highly recommend and look forward to staying here again!!
Superhost
Home in Killington
4.89 out of 5 average rating, 288 reviews

25 Rocky Ridge Road: Ski Home for Groups. Hot Tub.

JayRating, 5 stars1 month ago
The house was exactly what we were looking for. It was at most 8 minutes from the bottom of the mountain. Super easy to get to and fron everything at Killington. Classically, the first morning we forgot gloves, then skis, then a helmet. Doing the roundtrip from the mountain was easy. The house was exactly as discribed and perfectly appointed for a ski house. Kids loved the foosball table. Kitchen was easy to use and had plenty of fridge space, cooking areas, and seating. The two living rooms allowed people space to decompress differently. Bedrooms were well sized and had plenty of sleeping areas. The hot tube was hot! Simple Vacation was highly responsive and a great host. We couldn't have asked for more. It was exactly what we were looking for and we will be back.
Guest favourite
Home in Warren
4.92 out of 5 average rating, 206 reviews

Beautiful guesthouse -perfect for long stays

BriannaRating, 5 stars6 months ago
Very nice host !! Airbnb was very cozy and accessible, would highly recommend :)
Guest favourite
Home in Winooski
4.94 out of 5 average rating, 129 reviews

Spacious Winooski Oasis, close to downtown!

GauraviRating, 5 stars1 week ago
We had a great stay here. The house was quaint and exactly as pictured. We asked for recommendations but didn’t receive a response. However, Sam was super responsive for all other things house related like check in time and when the shower pump was broken and only giving us cold water. The hot water issue was taken care of right away which was appreciated! The backyard is big and fenced in. This is great for dogs! There is a grill and fire pit. We didn’t use either but having that amenity was nice. Location is great and so was the price. Walking distance and car ride from most eateries and cute shops. We felt safe, thank you!
Top Guest favourite
Home in Stowe
4.95 out of 5 average rating, 184 reviews

New Remodel w/VIEWS! on 20 Acres!

Carla Rating, 5 stars1 month ago
Kim was super kind and went above and beyond to help me sort out a situation even before our arrival. The home is located in a quiet beautiful area, it is super comfortable, beautifully decorated. The beds were very comfortable. We had plenty of towels and linens. My kids enjoyed playing games in the basement, and my husband and I enjoyed watching TV and reading by the fireplace. I highly recommend Kim's place.
Top Guest favourite
Home in Hartford
4.97 out of 5 average rating, 103 reviews

Luxury Barn Home w/Hot Tub, Sauna, Gardens MtnView

DianeRating, 5 stars3 months ago
This is my second time staying at Hilary’s home, and for good reason! My family loved gathering by the fireplace everyday, using the hot tub and sauna, and cooking dinners for our group of 8 in the well equipped kitchen every night! Plenty of room for us to spread out. Also love how close it is to the town of Woodstock (adorable with great shopping!) Hilary is very responsive and I am sure we will be back for a 3rd time at some point.
Guest favourite
Home in Colchester
4.96 out of 5 average rating, 126 reviews

Lake Champlain Colonial

ErikaRating, 5 stars2 weeks ago
We were 2 couples visiting children at UVM. The house was close enough to campus to go back and forth easily. The large kitchen and dining room meant we could cook big family dinners and sit around the table together - something we miss while they're at school. The rooms were large and clean with ample drawers and closet space and 8 of us easily slept there the night the kids stayed over. Bathrooms were great as well. We brought rackets and were able to use the public tennis courts right up the road. If the weather were nicer I'm sure we could have grilled and taken advantage of the huge back yard. There were 2 spots in the large, clean garage and plenty of driveway parking. All in all it was a much more affordable, versatile place to stay than downtown hotels.
Superhost
Home in Morristown
4.84 out of 5 average rating, 186 reviews

Green Mountain Getaway

KatRating, 5 stars1 month ago
We came to ski at Stowe last minute with two other family members and our two pups. The house was perfect for us and minutes to Stowe village. It’s very spacious and homey. We had a wonderful time!

Private house rentals

Guest favourite
Home in Milton
4.95 out of 5 average rating, 84 reviews

Waterfront * Sunsets * Private * Swimming/Fishing

KevinRating, 5 stars4 months ago
On our last day we saw a spectacular sunset which was indicative of our whole stay. The star was of course the wonderful setting on the lake. It was enhanced by how tastefully the house was renovated, decorated and fully supplied with everything we needed. It truely exceeded our expectations and made for a memorable experience in the beautiful state of Vermont.
Guest favourite
Home in Warren
4.97 out of 5 average rating, 102 reviews

Bluebird Cottage - Three Min to Sugarbush Resort

WhitneyRating, 5 stars1 week ago
Colin's place was great for our Easter with our four children and two grandchildren. Location is convenient to Sugarbush and surrounding attractions.
Superhost
Home in Waitsfield
5 out of 5 average rating, 3 reviews

FULL HOUSE w/HOT TUB - Waitsfield Common

LauraRating, 5 stars6 months ago
This home is beautiful, spacious and is surrounded by nature. The backyard had a huge deck with a tree lined backyard and you can hardly see the next neighbour. There are rolling hills and cows in the next pasture. So serene. The house has lots of room in the main area for our family, it never felt crowded. The kitchen looks better then the pictures, with a huge island and the entire house is fully stocked. You can tell this is not just a rental as it had more then we expected to live comfortably. She was also kind enough to bring us some baby items. The location is great as wherever you turn it's beautiful but also within driving distance to Stowe. The local towns are really cute too. Our family really enjoyed our time here.
Guest favourite
Home in Killington
4.94 out of 5 average rating, 117 reviews

Cozy Private House on Killington Mtn - Hottub

MeganRating, 5 stars1 month ago
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.
Superhost
Home in Morrisville
4.92 out of 5 average rating, 12 reviews

Morrisville's Cottage Style Coziness

DianaRating, 5 stars12 months ago
Sherry's cottage was the perfect place for our family to view the eclipse from! The place was well-equipped with everything we needed and spotless. Would definitely stay again!
Superhost
Home in Bakersfield
4.91 out of 5 average rating, 156 reviews

Northern Vermont Country Escape/ The Martin House

ViktorRating, 5 stars1 month ago
Thank you very much, Robin. The house is located in a cozy picturesque place. The weekend was wonderful. The house has all the amenities, and the hot tub is just super. We went skiing in the neighboring resorts, saw the sights. I recommend this wonderful place.
Superhost
Home in Grand Isle
4.87 out of 5 average rating, 156 reviews

Gorgeous 1835 Farmhouse w. Lake/MTN Views!

Maria Del CarmenRating, 5 stars3 months ago
It is a beautiful house where you can smell the family and we liked that a lot. It is close to the ski slopes, very clean and comfortable. Lidsa and Tom have very good communication, excellent service.
Guest favourite
Home in Stowe
4.94 out of 5 average rating, 189 reviews

Huge deck, hot tub, foosball, surrounded by nature

MaritaRating, 5 stars1 month ago
Great stay at Jen’s beautiful chalet. Easy to communicate with and well equipped with many kitchen supplies and all the needed towels, linens, hairdryers, and a thoughtful welcome package. Only about 15 mins from the mountain and 10 mins to town. Thanks!

Quick stats about house rentals in Middlesex

  • Total rentals

    70 properties

  • Nightly prices starting at

    $94 AUD before taxes and fees

  • Total number of reviews

    5.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Washington County
  5. Middlesex
  6. House rentals