
Pet-friendly vacation rentals in Middlesex
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Middlesex
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

The Rustic Retreat at Twin Ponds
Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

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.

Entire 2nd Floor Walk to Montpelier
Five minute walk to the prettiest and coolest state capital in the country. Entire second floor duplex with separate entrance up a flight of stairs. Beautiful porch. Perfect base to explore Vermont; hiking, skiing, biking. Hosts live downstairs. Dogs are welcome with conditions. (Note the reservation requirements) Limit 4 people. (Includes toddlers and infants) If you are a skier, we're e less than an 40 minutes to major Ski areas. You won't have to pay resort prices and have a more room.

Peaceful setting with Mountain Views
Rent the entire house. Large primary bdrm w/ private bath and 2 bdrms that accommodate 4 people w/ a shared full bath, one bonus room with pull out couch. Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (available from Memorial Day till Thanksgiving), outdoor fire pit, all on 8 acres. Located centrally to three ski resorts, mountain biking, hiking , kayaking, swimming, you name it. An inviting home in any season!

Waterbury Center Guest Bedroom - 244 Howard
The guestroom room has a separate entrance located off a covered, back porch with a small table and chairs for summer use. There is adjustable heat and cool air from the wall mounted air-source, heat pump. The little kitchen alcove is convenient for coffee or tea or a light meal (toaster oven, single induction “hot” plate, water heater) We live in a historic building. Our neighborhood is very close to Rte 100. Waterbury village and Stowe are nearby too with skiing, hiking and biking.

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

The Cottage on Sterling Brook
Escape and relax in the peaceful atmosphere of Sterling Brook. 🍁 Comfortable & cozy interior leads onto a wrap-around deck right on the banks of Sterling Brook, beautiful in every season. 🍁 Keep an eye out for the local otters playing in the brook while drinking your morning coffee. 🍁 This serene hideaway offers a peaceful retreat in nature, leaving you rested and recharged. Conveniently located on the outskirts of Stowe. Sleeps 3. Dog-friendly with approval. 🍁🦦🍁

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.

Cozy Hideaway w Hot Tub — Perfect for Ski Weekend!
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.

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 pet-friendly home rentals
Pet-friendly house rentals

Mountainside Lodge, near wedding barns/Stowe

Captain Tom's Cabin - Secluded Vermont Getaway

Epic Views of the Green Mountains

Mid century modern gem with views of Sugarbush

Cozy net zero apartment

Modern design in the woods, private, beautiful

The Guest House at Sky Hollow

Vermont Ski Chalet Close to Sugarbush and Stowe!
Pet-friendly home rentals with a pool

Relax in Recreation Paradise!

Secluded Paradise on the Connecticut River, VT

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 Studio Ski in Ski Out | 145

Cozy Little Mountain Condo
Private, pet-friendly home rentals

Romantic NEK Log Cabin w/ Hot Tub & Fireplace

Vermont Treehouse in the Woods with Sauna & Stream

NEW! Studio Loft in Stowe Hollow

Scandinavian design Cabin hiking trail + hot tub

Epic Luxury Treehouse - next to Dog Mountain !

Serene Country Cabins 1 In the heart of Vermont

Waldhaus - Modern Forest Cabin

3br Chalet with Amazing Views of Mt. Mansfield
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $360 CAD | $291 CAD | $288 CAD | $192 CAD | $255 CAD | $246 CAD | $302 CAD | $274 CAD | $285 CAD | $281 CAD | $274 CAD | $306 CAD |
| 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 vacation rentals that are pet-friendly in Middlesex

Total vacation rentals
Explore 30 vacation rentals in Middlesex

Nightly prices starting at
Middlesex vacation rentals start at $82 CAD per night before taxes and fees

Verified guest reviews
Over 4,030 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Middlesex vacation 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!
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- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Jay Peak
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Stowe Mountain Resort
- Montshire Museum of Science
- Dartmouth College
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Shelburne Museum
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- Middlebury College
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- Warren Falls
- Waterfront Park
- Lake Champlain Chocolates
- Snow Farm Vineyard & Winery
- Elmore State Park




