Family-friendly holiday rentals in Middlesex

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Popular amenities for Middlesex family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Stowe
4.92 out of 5 average rating, 357 reviews

The Rabbit Hole - Luxury Cabin in heart of Stowe

SuzanneRating, 5 stars1 month ago
The house was perfect for us. We were a group of 8 and everyone had a comfortable place to sleep, plenty of space to move around, park our cars and sit while relaxing throughout the house. Ryan was so helpful and quick to respond if we had any questions. Lovely house, hope I get to return.
Guest favourite
Yurt in Randolph
4.94 out of 5 average rating, 456 reviews

Upper Yurt Stay on VT Homestead

JillianRating, 5 stars1 day ago
Jonathan communicated well and the place was beautiful - would definitely come back again !
Guest favourite
Cabin in Starksboro
4.88 out of 5 average rating, 284 reviews

Charming getaway tucked away in the Green Mtns

TraceyRating, 5 stars4 weeks ago
Not sure if it was the mattress, the sheets and quilt, the pillows, the Vermont woods, Vermont fresh air, or the rain hitting the roof… maybe all of it… but, my husband and I have not slept so well in… maybe EVER! Rob’s home is super comfy and dog friendly. The hot tub is a nice feature and works wonderfully. If you are looking for a quiet, peaceful location for your visit, this hits all the marks. Sitting outside with your morning coffee is a treat. If weather doesn’t cooperate, recommend sitting in the den in front of the picture window. Our old dog truly appreciated exploring the fenced yard, and we loved allowing him off off-leash. Great place to stay!
Top Guest favourite
Home in Stowe
4.95 out of 5 average rating, 108 reviews

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak

BrianRating, 5 stars3 weeks ago
This place was perfect for our family of three for a long weekend. The room had everything we needed and the views of the village from the balcony were amazing. Lots to do in the village and plenty more just a short drive down the road to Stowe. We’d love to come back in the summer when there are more outdoor activities available.
Guest favourite
Apartment in Hinesburg
4.93 out of 5 average rating, 287 reviews

Hilltop Haven

LeahRating, 5 stars2 days ago
We had a wonderful stay at the Monty's place -- the apartment was well stocked with many thoughtful items, the area is very peaceful and near to outdoor activities, and the hosts were friendly and responsive. Would definitely stay again! Thank you!
Guest favourite
Home in Stowe
4.94 out of 5 average rating, 189 reviews

Huge deck, hot tub, foosball, surrounded by nature

MaritaRating, 5 stars2 months 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!
Top Guest favourite
Home in Stowe
4.98 out of 5 average rating, 267 reviews

EPIC Stowe Getaway - Great For Families & Friends

KatieRating, 5 stars2 weeks ago
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!
Superhost
Apartment in Morristown
4.92 out of 5 average rating, 221 reviews

Cozy Country Apartment with private hot tub

AbbeRating, 5 stars3 months ago
Steve's place was great! Reasonably close to Stowe, easy to check in and out, and as described in the listing.

Family- and pet-friendly home rentals

Guest favourite
Cabin in Hyde Park
4.94 out of 5 average rating, 589 reviews

Dream Cabin in Vermont

RebeccaRating, 5 stars6 days ago
We absolutely adored our stay at the cabin. It is idyllic inside and out! It was amazing to come home to after a day of exploring. The bed was super comfortable and the highlight for us was watching VHS on the TV with snacks. It is so well equipped and cosy, also enjoyed a lovely bath in the claw foot tub. Just perfect for a rustic, cosy stay in nature. A highlight for me was stepping outside at night and listening to (I assume they were) frogs!! They were so loud and it was incredible to hear them, the trees were also surrounded by fireflies (I’d never seen them before!) and I’ll always remember that perfect moment of peace. Thank you for making our 10 year anniversary so memorable with such a lovely place to stay, if you’re thinking of it for a special occasion or just as a base to explore this adorable region of Vermont, look no further :) thank you!
Guest favourite
Cabin in Woodstock
4.95 out of 5 average rating, 200 reviews

Hideaway Cabin by the Stream on 27 Acres

JenniferRating, 5 stars2 weeks ago
Our stay was incredible! The view by the stream was amazing, everything was so peaceful and perfect. Inside the cabin was exactly what we expected, very homey, everything we needed. We loved the walls lined with books! Kevin was very attentive towards what we needed - it stormed all day Saturday and he brought a second heater for us because the temperature dropped, which with that and the gas fireplace, kept the place perfectly warm and comfortable. He was also very accommodating in allowing us to stay an extra night since our plans of hiking all weekend were thwarted by the rain. We went for my husband's 40th birthday and i couldn't have picked a better place to get away from the stress of life. We plan on going back for sure!
Guest favourite
Home in Stowe
4.98 out of 5 average rating, 159 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

JohnathanRating, 5 stars3 months ago
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.
Top Guest favourite
Apartment in Hardwick
4.94 out of 5 average rating, 104 reviews

Peaceful retreat overlooking park (Apartment 3B)

PaigeRating, 5 stars3 months ago
Claudia's place was PERFECT! If you are looking to explore Hardwick this is the only way to do it, easy check in and check out and literally spackle dab in the middle of town! Did I mention it's right above one of the most amazing coffee shops, with a great space to work, people with and enjoy delicious homemade bake goods and breakfast sandwich! I also enjoyed positive pie and cork and fork! Thank you so much for everything, felt right at home!
Top Guest favourite
Cabin in Topsham
4.99 out of 5 average rating, 293 reviews

Pine Cabin, Galusha Hill Farm, incredible view!

BridgetRating, 5 stars2 weeks ago
We loved our stay and hope to come back again!
Guest favourite
Cabin in Hyde Park
4.95 out of 5 average rating, 354 reviews

Serene Country Cabins 1 In the heart of Vermont

EdwardRating, 5 stars2 weeks ago
Great little cabin for a weekend stay for my wife and I and our dog. Easy access to town for necessities and close to several local breweries. Would definitely stay here again.
Top Guest favourite
Apartment in West Glover
4.98 out of 5 average rating, 537 reviews

The Lodge at Blackberry Hill

MargaretRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. the space was very comfortable, clean, well equipped, and in a beautiful setting. We highly recommend this location!
Top Guest favourite
Cabin in Groton
4.99 out of 5 average rating, 640 reviews

Peaceful Log Cabin in the Woods

RimRating, 5 stars1 week ago
This cabin was such a dream. Tucked away in the woods, it gave us the perfect mix of peace, nature, and comfort. Everything was clean and so well equipped. it had everything we needed and more, which made our stay super easy and relaxing. My boyfriend and I really appreciated the quiet, peaceful, cozy vibe. We felt completely at home and could just unplug and enjoy the moment we spent our time playing board games, sipping coffee in the garden or making dinner together in the cute little kitchen. Emily was an absolute pleasure: very kind and thoughtful, and great to talk to. You can tell she really cares about the space and the people who stay in it. We left feeling refreshed, happy, and already dreaming of coming back.

Family-friendly home rentals with a pool

Superhost
Condo in Stowe
4.81 out of 5 average rating, 284 reviews

Spacious Stowe condo Amzing views w/shared hot tub

JeffRating, 5 stars2 months ago
great place close to Stowe.
Guest favourite
Home in Granville
4.96 out of 5 average rating, 145 reviews

Epic Views of the Green Mountains

ColbyRating, 5 stars1 week ago
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.
Guest favourite
Guest suite in Ryegate
4.92 out of 5 average rating, 229 reviews

Secluded Paradise on the Connecticut River, VT

JatinRating, 5 stars3 weeks ago
beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.
Superhost
Guest suite in Jericho
4.74 out of 5 average rating, 292 reviews

Apartment, comfy and cozy with kitchen/gas fire

DavidRating, 5 stars6 days ago
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.
Superhost
Cabin in Mountain Lakes
4.92 out of 5 average rating, 165 reviews

Hilltop View Lodge - White Mountains, NH

AndrewRating, 5 stars3 months ago
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
Top Guest favourite
Townhouse in Stowe
4.87 out of 5 average rating, 214 reviews

Gorgeous panoramic views - 4 miles to the mountain

RuthRating, 5 stars2 months ago
Absolutely wonderful stay! As a family of five, we couldn't have asked for a better place. The unit was incredibly spacious, comfortable, and had such a warm, homey feel—it truly felt like a home away from home. The mountain view from the living room window was beautiful, a perfect backdrop for our mornings and evenings. Jeff, the host was exceptional—extremely responsive, thoughtful, and helpful throughout our stay. Every question or request was handled quickly and kindly, which made our experience stress-free and enjoyable. We had some wifi issues which took time to resolve but Jeff helped and made sure it is taken care of. The apartment was impressively well-equipped with everything we needed, clearly a lot of care went into preparing the space for guests. The location was perfect for us— surrounded by beautiful trails that we explored as a family. If you are into skiing, the ski tracks are short drive away. It was the ideal base for both adventure and relaxation. Highly recommended
Superhost
Cottage in Stowe
4.77 out of 5 average rating, 241 reviews

Cute Cottage - Poolside - Minutes To Activities

ChrisRating, 5 stars2 months ago
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.
Guest favourite
Condo in Killington
4.93 out of 5 average rating, 455 reviews

Hike bike golf 1 bedroom 1 nght Ok shuttle

ScottRating, 5 stars1 month ago
Great place great stay as always !!

Quick stats about holiday rentals that are family-friendly in Middlesex

  • Total rentals

    70 properties

  • Nightly prices starting at

    $116 NZD before taxes and fees

  • Total number of reviews

    4.8K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 properties include access to Wi-Fi

Destinations to explore