
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.

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.

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.

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

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.

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe
At this quiet 2BR on five green acres, you’ll start your mornings with coffee by the pond and end your days by the fire. Bring your bikes to ride over to Cady Hill, snow shoe or hike in Smuggler’s Notch, or stroll the flat mile into town for dinner. Inside, you’ll find toxin-free cookware, natural fiber bedding, and crisp spring-fed water straight from the tap. With a bunk room for the kids and a king suite for you, it’s a calm, well-kept base for year-round adventure in Stowe.

Peaceful Log Cabin in the Woods
This log cabin is set in the woods in a rural part of northeastern Vermont. Escape the hustle and bustle, clear your mind, and enjoy nature. A great place to get some fresh air or to stay in and take a nap. Beautiful summers for easy hikes and refreshing swims in the lakes of our local Groton State Forest, unbelievable foliage to view from small dirt roads, and tons of outdoor winter activities. Great for a couples getaway, friends weekend, or some quality time with the family.

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub
Welcome to our cozy retreat nestled in the picturesque town of Waterbury, Vermont. This newly renovated spacious and modern home is perfect for families or groups looking for a comfortable and stylish retreat. With its prime location, you’ll have easy access to local attractions, outdoor activities, renowned craft beer scene, world-class skiing, hiking trails, and breathtaking Mountain View’s - making it an easy getaway choice for nature lovers and outdoor enthusiasts.

Waterbury Village Hideaway with a HotTub!
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

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

Spacious Eco-Friendly Stowe Home for Family Fun

Wright’s Mountain Retreat with Sauna

The Guest House at Sky Hollow

Vermont private retreat with gorgeous views.

Dawnside - Green Mtns Home with White Mtns View

CLASSIC VT STYLE

Green Mountain Getaway
Pet-friendly home rentals with a pool

Mountain View Farmhouse w/ Orchard White Christmas

Relax in Recreation Paradise!

Epic Views of the Green Mountains

Lower Yurt Stay on VT Homestead

Cute Cottage - Poolside - Minutes To Activities

EPIC Stowe Getaway - Great For Families & Friends

3BR Stonybrook * Near Mountain Rd and Trapp Family

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

Studio suite in Barre

BEARfoot Bungalow

Magical Karma Cabin in the Woods

Cozy Treehouse with Sauna in the Woods with Stream

Neighboring the oldest Covered Bridge in VT!

Casita Cabin -Sun drenched cozy cabin on homestead

Charming log cabin w/ fireplace in Stowe village

The Guest House at Chandlery Farm
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $368 CAD | $298 CAD | $295 CAD | $197 CAD | $261 CAD | $252 CAD | $309 CAD | $281 CAD | $292 CAD | $295 CAD | $288 CAD | $350 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 $70 CAD per night before taxes and fees

Verified guest reviews
Over 3,830 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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- Sugarbush Resort
- Jay Peak Resort
- Bolton Valley Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Jay Peak Resort Golf Course
- Autumn Mountain Winery
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- Pump House Indoor Waterpark
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- Montshire Museum of Science
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- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Burlington Country Club
- Country Club of Vermont
- Killington Adventure Center
- Vermont National Country Club
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