
Family-friendly holiday rentals in Middlesex
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Middlesex
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

The Birch Perch! Treehouse with spa and fire pit!
Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

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.

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.

Treehouse at Bliss Ridge Farm - Best Views in VT!
This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

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

Home on Flower Farm near VT’s best skiing & brews!
Country setting adjacent to a flower farm only 3 minutes off 89 perfectly nestled between mountains that boast hiking, skiing and mountain biking and the best of Vermont's brewery and restaurant scene. 20 minutes to Sugarbush and Mad River Glen, 30 minutes to Stowe and 25 minutes to Bolton Valley (night skiing!). With Waitsfield and Waterbury being less than 10 minutes away, it's an easy drive to two of the finest breweries, Lawsons and Prohibition Pig, that Vermont has to offer.

Farmhouse with Sunset Mountain Views
Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, 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 Village, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

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.

Morningstar Meadow - your home in Vermont
You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Recent guests claimed heat an issue. It is not. No complaints before or since.

True Mountain House
This is a very private mountain home surrounded by green and peace. Your private forest. Amazing Views. Very romantic. Open layout. Lots of light. Wood floors and electric heating. Very quiet, relaxing and cozy. It has a decompressing effect on it's guests. Perfect to rest your head. Not suitable for children under 12 years old. Amazing gourmet kitchen. WE HAVE HIGH SPEED INTERNET. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.

Pet Friendly Cozy Treetop Cabin near Mt Worcester
Come get Vermonty like a local. A quiet sanctuary home base for adventure. Pick raspberries, climb a mountain, and cool off in a swimming hole. Far away from it all yet close to all you want to do. Wake up to a tree top sunrise. Have coffee in the hammock while watching the birds. Spend your days skiing fresh powder or apple picking and return home to quirky records, books, and games. Well-behaved pets welcome. Extensive seasonal local guide upon booking.

Travelers Oasis in Montpelier
We are SuperHosts! Our average is 4.86 stars. We recently had to change the hosting account for this apartment: To see reviews: http://airbnb.com/h/travelers-oasis-reviews this listing is absolutely the same. Travelers will experience a beautiful and comfortable resting space in this upstairs apartment in the heart of Vermont's state capital, Montpelier. Uniquely renovated space that gives one the impression of being in a boat.
Popular amenities for Middlesex family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Bow House Perched in Trees w/ Hot Tub & View

Stowe Sky Retreat: Hot Tub/Views/Family Friendly

The 1919 Mountain Farmhouse, new hot tub and patio

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Haven Tiny House by Stowe | Hot Tub, Sauna & Views

Scandinavian design Chalet hiking trail + hot tub

Secluded Luxury Treehouse - Hot Tub + Projector

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub
Family- and pet-friendly home rentals

Cozy Cottage in the Mad River Valley

Studio suite in Barre

Tiny House at Camp Comyns

Cozy VT Barn by Burlington-Firepit-BringUrDog-WiFi

Cady’s Falls Cabin

Fairytale cabin at The Wild Farm

Song Bird Sangha Yurt

Birch Tree Cabin! Pets Welcome!
Family-friendly home rentals with a pool

Mountain View Farmhouse w/ Orchard, Hummingbirds

Stowe, Newly Renovated Topnotch Resort Townhouse

Lower Yurt Stay on VT Homestead

Cute Cottage - Poolside - Minutes To Activities

Serene Mountain Studio Spruce Peak Lodge | 1328

Hill Top Apartment With Amazing View Near Stowe

Cozy/Private, close to hospital, i-89

Château Chavis
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $473 NZD | $473 NZD | $410 NZD | $339 NZD | $339 NZD | $339 NZD | $382 NZD | $349 NZD | $378 NZD | $404 NZD | $339 NZD | $482 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 holiday rentals that are family-friendly in Middlesex

Total holiday rentals
Explore 70 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at $119 NZD per night before taxes and fees

Verified guest reviews
Over 5,790 verified reviews to help you choose

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, Wifi 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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- Rentals with a fire pit Middlesex
- Family-friendly rentals Washington County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Jay Peak
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Dartmouth College
- Stowe Mountain Resort
- University of Vermont
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Middlebury College
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Waterfront Park
- Quechee Gorge
- Snow Farm Vineyard & Winery
- Kingdom Trails
- Fairbanks Museum & Planetarium




