
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.

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.

Worcester Mountain Cabin · Wildlife & Cozy Nooks
A modern cabin retreat in Vermont’s wild, undeveloped Worcester Mountain Range. Surrounded by wildlife, forest views, this cozy hideaway features a curated library, record player, art supplies, and space to create or simply rest. Explore local culture, skiing, swimming holes, and soulful retreats — or settle in, light a candle, and do nothing at all. Well-behaved pets welcome (the backyard is a dog’s dream). After booking, enjoy our insider welcome guide with local trial maps and hidden gems.

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.

Fairytale cabin at The Wild Farm
Lay in bed and look out the huge picture window at the farm. You might see cats climbing trees, hummingbirds, snowflakes falling, lightning storms and many more beautiful moments. We have a Wolf, don't be alarmed she is as friendly as can be and will greet you and escort you to the cabin. If you like nature, animals, walking in the forest, cuddling up by the wood stove, then this is the place for you. The cabin is surrounded by gorgeous perennial gardens. We look forward to hosting you!

Magical cabin with amazing views
100 year old , freshly renovated cabin that is in the middle of five 100 year old apple trees with incredible Mountain View’s. The cabin sits 100ft uphill from my 1842 brick farmhouse and is surrounded by apples trees, an ancient elm tree, fields and my berry patches. The huge deck has a dining table, lots of seating and and outdoor shower. Off the side of the deck are two claw foot bathtubs with hot and cold water for you to soak in. Note, tubs aren’t usable during the freezing months.

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

Cozy Cabin at Waterbury Center
Leaf peeping season is here and the latest report is that the leaves are just beautiful! We are located near Stowe, Ben and Jerry's , Burlington. Well-behaved dogs welcomed! One queen bed, air mattresses available. Best for couples, three people is ok, four is tight but do-able. Hot water, microwave, Keurig , refrigerator. Fans, TV (requires you to use your own log in, no cable TV.) Great WIFI. Bathroom is very clean with new toilet, new shower and antique sink. Cozy glamping!

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.
Popular amenities for Middlesex pet-friendly home rentals
Pet-friendly house rentals

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

Captain Tom's Cabin - Secluded Vermont Getaway

Mountain View Farmhouse w/ Orchard White Christmas

Epic Views of the Green Mountains

Spacious Eco-Friendly Stowe Home for Family Fun

Wright’s Mountain Retreat

Modern design in the woods, private, beautiful

The Guest House at Sky Hollow
Pet-friendly home rentals with a pool

Relax in Recreation Paradise!

3rd Floor Studio @ The Lodge at Spruce Peak

Lower Yurt Stay on VT Homestead

Cute Cottage - Poolside - Minutes To Activities

EPIC Stowe Getaway - Great For Families & Friends

Bunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool

Lodge At Spruce Peak Lux Studio | 1125

InSmuggs 5* 6 Daycations daily inc Mtn. View!
Private, pet-friendly home rentals

Cozy 1 bedroom loft apartment

Magical Karma Cabin in the Woods

NEW! Studio Loft in Stowe Hollow

Cozy & Peaceful Cabin on 40 Acres - Pups Welcome

Modern, Rustic Stowe Studio Apartment with a View

Pine Cabin, Galusha Hill Farm, incredible view!

Epic Luxury Treehouse - next to Dog Mountain !

Long Trail Suite - The Lodge at Wyckoff Maple
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $262 | $212 | $210 | $140 | $186 | $179 | $220 | $200 | $208 | $210 | $205 | $249 |
| Avg. temp | 21°F | 23°F | 32°F | 46°F | 58°F | 67°F | 72°F | 71°F | 63°F | 50°F | 39°F | 28°F |
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 $50 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 & 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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