
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.

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, will you wake to coffee on the deck surrounded by nature? Or build a fire + cozy up on the couch? Perhaps a hike? Why not simply stay in bed and admire the view? The choice is yours!

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.

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.

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

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.

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.

Spacious Eco-Friendly Stowe Home for Family Fun
Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

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

Captain Tom's Cabin - Secluded Vermont Getaway

Epic Views of the Green Mountains

Modern Farmhouse on 25 Acres - Superb Views

Modern design in the woods, private, beautiful

Enjoy fall foliage from the hot tub!

The Guest House at Sky Hollow

Forest Hideaway
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!

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

Cozy Cabin at Waterbury Center

Pine Cabin, Galusha Hill Farm, incredible view!

VT Hideaway studio: breweries,hiking, dogs welcome

Sunday Mountain Surprise

Waldhaus - Modern Forest Cabin

"Mansfield" Suite - The Lodge at Wyckoff Maple

Peaceful Log Cabin in the Woods
Quick stats about vacation rentals that are pet-friendly in Middlesex
Total rentals
30 properties
Nightly prices starting at
₱2,910 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Rentals with a fireplace Middlesex
- Pet-friendly rentals Washington County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Burlington Country Club
- Leahy Center for Lake Champlain
- Mt. Eustis Ski Hill
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
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