
Pet-friendly vacation rentals in Middlesex
Find and book unique pet-friendly homes on Airbnb
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 R 960 ZAR per night before taxes and fees

Verified guest reviews
Over 3,900 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!
Top-rated pet-friendly home rentals in Middlesex
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Mountain View Farmhouse w/ Orchard, Pool is Open!
This magical property is Vermont at its finest. Bring the whole family to this idyllic farmhouse with panoramic mountain views, large private pool, apple orchard, flower gardens, fire pit and much more. Be as free as you imagine on 14 private acres of lawn, perennial gardens, fruit trees and lush woods with a meandering stream. Let the kids swim in the pool all day while you read in the shade of old locust trees while taking in one of the best views in Vermont.Find us on insta: @upper_east_eden

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.

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.

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.

Waterbury Center Guest Bedroom - 244 Howard
The guestroom room has a separate entrance located off a covered, back porch with a 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 w/ toaster oven, single induction “hot” plate, water heater & small fridge We live in a historic building. Our neighborhood is near Rte 100. Waterbury village and Stowe are nearby with skiing, hiking and biking too.

Stunning Views near Stowe /Mountain private home
Retreat and relax at this incredibly located & 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 minutes to the attractions of Stowe, Waterbury and Mad River Valley. Enjoy the hiking trails very close to this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

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.

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.

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.

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.

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.

44 Degrees North
This cozy 3 bed 2 bath cabin is situated on the southern end of the Worcester Range in Waterbury Center. Enjoy beautiful sunsets over Camel's Hump and Bolton Mnt while sipping cocktails on the deck. Or warm up in the in the hot tub during the winter while watching the cats groom the trails at Stowe . Hike, bike and snowmobile from your doorstep or treat yourself to VT craft beers and eats just a short 5-7min drive away.
Popular amenities for Middlesex pet-friendly home rentals
Pet-friendly house rentals

Vermont Cedar Cottage | Fireplace & Pond Views

Cozy Mountain Home w/Million $ View

Best of Both - Quiet woodland home near activities

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

SylvanRhapsody-Stowe Village OutDoor Hot-tub!

CLASSIC VT STYLE

Modern Barn Perched on 24 Acres w/ Stunning Views

Forest Hideaway
Pet-friendly home rentals with a pool

EPIC Stowe Getaway - Great For Families & Friends

Cozy/Private, close to hospital, i-89

World-Class Villa @ Trapp & Stowe

UNIQUE, BEAUTIFUL HOME w/ 30 ACRE FARM

Château Chavis

Lakefront Peaceful Getaway in Mountain Lakes

Charming Barre Getaway

Cute Cottage - Poolside - Minutes To Activities
Private, pet-friendly home rentals

Fabulous Fall Foliage on water in the heart of VT

Charming log cabin w/ fireplace in Stowe village

Modern Condo Filled with Natural Sunlight

Cozy Cottage in the Mad River Valley

Cady’s Falls Cabin

Renovated 4BD House: Hot Tub, Sauna & Backyard

The Rustic Retreat at Twin Ponds

The Cottage on Sterling Brook
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 3,647 ZAR | R 3,919 ZAR | R 3,167 ZAR | R 2,751 ZAR | R 3,231 ZAR | R 3,247 ZAR | R 3,519 ZAR | R 3,199 ZAR | R 3,327 ZAR | R 3,279 ZAR | R 3,199 ZAR | R 3,567 ZAR |
| 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 |
Destinations to explore
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- Jay Peak Resort
- Sugarbush Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Dartmouth College
- Jay Peak
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Cannon Mountain Ski Resort
- Killington Resort
- Jay Peak Resort Golf Course
- Kingdom Trails
- Montshire Museum of Science
- Snow Farm Vineyard & Winery
- Warren Falls
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Pump House Indoor Waterpark
- Quechee Gorge
- Elmore State Park
- Fairbanks Museum & Planetarium





