
Pet-friendly holiday rentals in Middlesex
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Top-rated pet-friendly home rentals in Middlesex
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Pet-friendly house rentals

Cozy Bow House Perched in Trees w/ Hot Tub & View
The Bow house was a beautiful place and Jen was incredibly hospitable and responsive. This is an amazing place to come and get away from the noise. Everything was so clean and cozy. Would definitely come again!

The Looking Glass, a modernistic escape
Overall we very much enjoyed modern rural space. Kiss the Cow farm about 5min drive was amazing& we got most all main food there w/ additional items from Barnard General Store. Spices/ cookware were very good - we brought nonstick pans& 1 knife to supplement. Plenty bowls, measuring cups/spoons, maybe a set of tom collins glasses would be nice albeit stemless wine and rocks glasses available. Needs garlic/onion powder. Tub was amazing/ upstairs bathroom a true getaway/ relaxing space. It was as pictured albeit note spiral staircase &open grated flooring upstairs. Plenty of windows albeit not much cross breeze so think ahead if bring own fan and/or start A/C before get too warm. I would say you must have an SUV year round for this rental - surrounding roads/ driveway are a good distance on rough dirt/gravel - traversable yet a sportier car with low profile tires/ ground clearance would not work. We enjoyed simply walking driveway& East Barnard Rd. Barnard Inn restaurant worth it.

Spacious Eco-Friendly Stowe Home for Family Fun
A beautiful Stowe getaway. The house has beautiful views of Mt. Mansfield, boasts plenty of space, and is in a great location relative to town.

Wright’s Mountain Retreat with Sauna
We loved spending our time in Vermont at Bonnie’s place! The house had everything we needed and Bonnie was a great and responsive host. The horses next door were such a treat for our kids to see and the views were beautiful.

Modern design in the woods, private, beautiful
Becca and Blake are excellent hosts. They were proactively communicative and their home was exactly as described in the listing. It was a seamless experience and a beautiful location!

The Guest House at Sky Hollow
This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!

Dawnside - Green Mtns Home with White Mtns View
Dawnside is just as beautiful in person as in the photos. We had a wonderful time and appreciated the views, privacy, and cleanliness of the property. Erich is a great host and the house manual is detailed and useful. We would visit again!

Maple Sugar Shack Tiny House w/hot tub & river by
Tyler’s tiny home was a very good stay. Location great, hot tub was amazing, and loved the loft. Bathroom was nice as well. We would stay here again for sure! The one downside was on our last morning, as we went to reach for some clean towels, only to find a bunch of dirty ones stuffed in the drawer with hair all over them. I would’ve let Tyler know but we had to be out quite early for checkout. I’m sure he would’ve taken care of it! I’d recommend this stay to anyone looking to explore Vermont, quick commute to Stowe, but also very private.
Pet-friendly home rentals with a pool

Epic Views of the Green Mountains
We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.

Secluded Paradise on the Connecticut River, VT
beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.

Relax in Recreation Paradise!
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

Lower Yurt Stay on VT Homestead
Beautiful spot to relax, reconnect and leave refreshed! We enjoyed everything about our stay, especially the sauna, living pool, and hike to the yurt! We would love to return, thank you for sharing such a peaceful place with us, it was exactly what we needed.

Apartment, comfy and cozy with kitchen/gas fire
We really enjoyed this place! The property is beautiful. The pool looked really clean and well cared for (but we didn't have a chance to use it). The supplied linens and especially the bath towels were great. This certainly will be on our list the next time are in VT.

Hilltop View Lodge - White Mountains, NH
Our stay was wonderful at the cabin. The cabin was clean and centrally located to winter activities. Andrea was very responsive. Cant wait to go back again

EPIC Stowe Getaway - Great For Families & Friends
weekend family trip for 6 of us and our dog(4 adults and 2 kids), plenty of space for everyone, and much larger than I expected! we enjoyed cooking in the well stocked kitchen, playing board games on the large dining room table, swimming in the pool and soaking in the hot tub, wrapping the nights up with a movie on their Roku TV! Kristin was very responsive in her communication, we had a lovely time and would love to plan future trips here again!

Cute Cottage - Poolside - Minutes To Activities
Linda was a fantastic host, and her home was even better than listed. The cabin was a good size for our family of four + dog; the 2 bed / 2 bath arrangement allowed for good privacy when needed. The fireplace was great for apres and winding down at night. Location is a nice mix of seclusion (off the Mountain Rd), but close to everything.
Private, pet-friendly home rentals

Magical Karma Cabin in the Woods
Our stay at the Karma cabin was beyond wonderful. We booked it hoping for a calm weekend away and it certainly delivered. The bedroom (2nd floor) has the bed facing a massive window so if you leave the curtains open you wake up to the most beautiful sight of trees— we spent hours just relaxing, watching the rain, the birds, and the gentle swaying of the branches. The kitchen was equipped with everything we needed to cook, and there was a bonus grill outside too! The Karma cabin was spotless when we arrived— it’s clear Claudia puts great care into the space. She shared lovely recommendations for nearby hikes, food options (great cafe called the Roastery a short drive away), and breweries. She was responsive and thoughtful, checking in if we needed anything. The fenced in yard was a huge bonus, we sat out with morning coffee (and sometimes breakfast) while our pup sniffed to her hearts content. We will definitely be back for another visit!

Tiny House at Stony Brook Farm
I loved my stay! The Airbnb was easy to find and the hosts gave me a friendly welcome once I arrived. Communication was easy before arrival as well. This cozy spot had everything you could need for a few nights stay. It was clean and peaceful. I really enjoyed having my morning coffee with a view of all of the sweet farm animals that reside on the property. I will be staying here again 🙂

Cozy Treehouse with Sauna in the Woods with Stream
The treehouse was such a relaxing mini vacation spot! We arrived to find a lovely welcome basket for our anniversary on the counter and a welcome book for the property. The stream and outside deck were better than the photos and we enjoyed eating dinner sitting on the deck. We met Heather and was friendly and super helpful with local recommendations! We have already recommended to a few friends and would love to return in the future:)

NEW! Studio Loft in Stowe Hollow
I think this is the best air bnb I’ve ever booked. You literally feel at home and it was so cozy & quiet. Super clean, had books & board games, Suzie was super responsive and the location was just amazing, super close to everything. Basically everything you want when searching for an air bnb. I will most definitely be booking again every time I come up!

Hydrangea House on the Hill
Sergjio's cabin was everything we could have wanted and more from a relaxing stay in Vermont. He greeted us and showed us inside the cabin, where he had wine and farm fresh eggs for us as a welcome gift. The cabin itself was beautiful and incredibly well kept. Sergjio also provided us with plenty of local recommendations for food and activities, which we thoroughly enjoyed. Finally, after our stay, he made checkout incredibly easy. We were absolutely blown away by Sergjio's hospitality, and will definitely be back in the future!

Spring & Summer on the Pond in VT
We loved this sweet cabin overlooking Curtis Pond. Great screened in porch, well-stocked kitchen, games, barbecue and fire pit. A great spot to relax and take advantage of VT summer.

The Cabin
Super cute area, definitely an authentic rural Vermont stay. Made us feel right at home in the nature. Outhouse made for an interesting new experience, but overall great get away.

"Mansfield" Suite - The Lodge at Wyckoff Maple
We had a great time at Thomas’ Mansfield Suite. Very comfortable and well appointed. We found a binder with news articles regarding the history of the building, which was housed UVM’s outdoors club in the 60’s. We would absolutely rent again.
Quick stats about holiday rentals that are pet-friendly in Middlesex
Total rentals
40 properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
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- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Bolton Valley Resort
- Spruce Peak
- Jay Peak Resort Golf Course
- Pico Mountain Ski Resort
- Cannon Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Fort Ticonderoga
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- Mt. Eustis Ski Hill
- Northeast Slopes Ski Tow
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Cozy Cottages & Otter Valley Winery
- Leahy Center for Lake Champlain
- Country Club of Vermont
- Montshire Museum of Science
- Burlington Country Club
- Lincoln Peak Vineyard
- Killington Adventure Center