
Pet-friendly holiday rentals in Middlesex
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Middlesex

Total holiday rentals
Explore 30 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at €53 per night before taxes and fees

Verified guest reviews
Over 3,940 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Middlesex holiday rentals include wifi 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!
Top-rated pet-friendly home rentals in Middlesex
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

The 1919 Mountain Farmhouse, new hot tub and patio
Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

Cady’s Falls Cabin
Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

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.

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.

Birch Tree Cabin! Pets Welcome!
A cute, cozy dream tucked away in the woods of Vermont. Completely private and yet close to everything. You can feel the warmth, charm, and uniqueness of Vermont. The fenced in area will be a great playground for your 4-legged family members! Home! We are aiming to create a eco friendly and living with nature environment. Part of that is to have an edible landscape during the warm months. From fruit trees to berries to herbs it is a wonderful experience for young and old. MRT-10102198

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.

Tiny House at Camp Comyns
NO check in. Total privacy. Tiny House with a big heart! This magical place is located 3 miles from Waterbury (I-89 exit 10), walking distance to Camel's Hump hiking trails and the Long Trail. Cross Vermont biking, VAST snow mobile trails, kayaking, swimming, fishing, skiing and more. Breathtaking views of mountains, gorgeous foliage. Great restaurants, breweries and live music all within five miles. Plenty of parking. Close to Stowe, Montpelier, and Burlington.

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.

Waldhaus - Modern Forest Cabin
Escape to our beautifully designed Vermont cabin, transformed into a modern, cozy, and sun-filled retreat. From the moment you step inside, you'll feel at home in this inviting space. The entire cabin & yard will be yours during your stay. High-speed fiber WiFi keeps you connected and dogs are welcome. We're just 15-20 min from Mad River Glen, Mt. Ellen & Sugarbush. Many restaurants & stores are within 15 min to Waitsfield, 20 min to Waterbury.

Cozy Cottage in the Mad River Valley
My dad and I built this home from 2015-2019 working mostly on the weekends. We did everything we could ourselves including all the framing, siding, and fine woodworking. It has abundant natural and artificial light and a beautiful deck/porch. We made sure to build a lot of storage space with built in closets, cabinets, and drawers. I am very proud of what we accomplished and I'm so excited to be able to share our creation with guests.

Cozy Hideaway w Hot Tub — Bike, Hike, Play & Relax
Welcome to our lovely 1865 Waterbury Village Hideaway. We are located 1/2 mile from the very best Mountain Biking trails, less than 1 mile to great food and beer, access to more than 7 Ski Resorts, including Stowe, Sugarbush & Killington, and 30 minutes from Burlington and the Waterfront. Use this Hideaway to take advantage of everything Vermont has to offer and relax in the soothing waters of our Hot Tub at the end of the day.
Popular amenities for Middlesex pet-friendly home rentals
Pet-friendly house rentals

Mountainside Lodge, near wedding barns/Stowe

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

Captain Tom's Cabin - Secluded Vermont Getaway

Spacious Eco-Friendly Stowe Home for Family Fun

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

Cozy net zero apartment

Wright’s Mountain Retreat

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub
Pet-friendly home rentals with a pool

UNIQUE, BEAUTIFUL HOME w/ 30 ACRE FARM

Mountain View Farmhouse w/ Orchard, Pool is Open!

Lower Yurt Stay on VT Homestead

Secluded Cabin Getaway Mountain Lake Community!

EPIC Stowe Getaway - Great For Families & Friends

Cute Cottage - Poolside - Minutes To Activities

Lodge At Spruce Peak Lux Studio | 1125

Cozy Little Mountain Condo at BV Ski Resort
Private, pet-friendly home rentals

Modern, Rustic Stowe Studio Apartment with a View

Fairytale cabin at The Wild Farm

Hilltop Retreat with Large Deck and Mountain Views

"Mansfield" Suite - The Lodge at Wyckoff Maple

Entire 2nd Floor Walk to Montpelier

Charming log cabin w/ fireplace in Stowe village

The Rustic Retreat at Twin Ponds

Magical cabin with amazing views
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €200 | €215 | €174 | €123 | €163 | €157 | €193 | €176 | €183 | €180 | €176 | €196 |
| 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 |
Destinations to explore
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- Jay Peak Resort
- Sugarbush Resort
- Pico Mountain Ski Resort
- Jay Peak
- Bolton Valley Resort
- Dartmouth College
- Killington Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- University of Vermont
- Middlebury College
- Jay Peak Resort Golf Course
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Kingdom Trails
- Pump House Indoor Waterpark
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- Shelburne Museum
- Warren Falls
- Elmore State Park
- Cold Hollow Cider Mill
- Quechee Gorge





