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

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.

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!

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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

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.

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.

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.

Forest Hideaway
Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails are nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.

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

Captain Tom's Cabin - Secluded Vermont Getaway

Mountain View Farmhouse w/ Orchard, May Flowers

Spacious Eco-Friendly Stowe Home for Family Fun

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe

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

Wright’s Mountain Retreat

Architectural House Prickly Mountain
Pet-friendly home rentals with a pool

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

Mountain Lakes. Pet friendly. Entire Chalet.

Lakefront Peaceful Getaway in Mountain Lakes

Cozy Little Mountain Condo at BV Ski Resort

Cozy/Private, close to hospital, i-89
Private, pet-friendly home rentals

Romantic NEK Log Cabin w/ Hot Tub & Fireplace

Cozy VT Barn by Burlington-Firepit-BringUrDog-WiFi

Modern, Rustic Stowe Studio Apartment with a View

Fairytale cabin at The Wild Farm

Song Bird Sangha Yurt

Boathouse Cabin on Lake Wapanacki with Sunset View

Serene Country Cabins 1 In the heart of Vermont

1 Acre Private Island Cottage (Sat Check In/Out)
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,915 GYD | G$44,435 GYD | G$44,016 GYD | G$29,344 GYD | G$38,985 GYD | G$37,518 GYD | G$46,112 GYD | G$41,920 GYD | G$43,596 GYD | G$42,968 GYD | G$41,920 GYD | G$46,740 GYD |
| 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 G$12,576 GYD per night before taxes and fees

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

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Middlesex vacation 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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- Pet-friendly rentals Washington County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Jay Peak
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Stowe Mountain Resort
- Dartmouth College
- 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
- Elmore State Park




