
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.

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.

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 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 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.

Hydrangea House on the Hill
The loft is surrounded by woods in a quaint, picturesque, rural part of Northwestern Vermont close to Burlington and Mad River Glen. We are 25 mins to Mad River Glen, Bolton Valley and Burlington (Lake Champlain beaches) and 10 mins to Sleepy Hollow Ski and Bike Center, Camel's Hump Nordic Ski Area, Frost Brewery and Stone Corral. Enjoy complete privacy and peaceful surroundings of nature with the full amenities of a home.

Miles Court Downtown Montpelier
Curious about what makes the Smallest State Capital so amazing? Come stay at Miles Court named after Anne G. Miles in the 1890's. This is a newly renovated space combining late 19th century charm with modern conveniences. Right in downtown Montpelier there's no need to drive to enjoy the multiple restaurants and entertainment. Plus we're 30 minutes from all the skiing. Were centrally located in the heart of Vermont.
Popular amenities for Middlesex pet-friendly home rentals
Pet-friendly house rentals

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

Mountain View Farmhouse w/ Orchard White Christmas

The 1919 Mountain Farmhouse, new hot tub and patio

Epic Views of the Green Mountains

Vermont Ski Chalet Close to Sugarbush and Stowe!

Peaceful setting with Mountain Views

Dawnside - Green Mtns Home with White Mtns View

Vermont private retreat with gorgeous views.
Pet-friendly home rentals with a pool

Relax in Recreation Paradise!

Lower Yurt Stay on VT Homestead

Cozy Studio Spruce Peak Lodge Ski in Ski Out | 319

Secluded Cabin Getaway Mountain Lake Community!

Cute Cottage - Poolside - Minutes To Activities

EPIC Stowe Getaway - Great For Families & Friends

Mountain Lakes. Pet friendly. Entire Chalet.

Lakefront Peaceful Getaway in Mountain Lakes
Private, pet-friendly home rentals

Cozy Cottage in the Mad River Valley

Cozy Treehouse with Sauna in the Woods with Stream

Cozy cottage in peaceful location

Cozy & Peaceful Cabin on 40 Acres - Pups Welcome

Cady’s Falls Cabin

VT Hideaway studio: breweries,hiking, dogs welcome

Earthen Yurt in Green Mtn Wonderland

Peace of Dirt Ranch
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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Jersey City Vacation rentals
- Rentals with a fireplace Middlesex
- Family-friendly rentals Middlesex
- Apartment rentals Middlesex
- Rentals with a fire pit Middlesex
- House rentals Middlesex
- Rentals with a washer and dryer Middlesex
- Rentals with outdoor seating Middlesex
- Rentals with a patio Middlesex
- Pet-friendly rentals Washington County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Sugarbush Resort
- Jay Peak Resort
- Bolton Valley Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Dartmouth Skiway
- Cochran's Ski Area
- Lucky Bugger Vineyard & Winery
- Jay Peak Resort Golf Course
- Autumn Mountain Winery
- Pump House Indoor Waterpark
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Mt. Eustis Ski Hill
- Ethan Allen Homestead Museum
- Burlington Country Club
- Leahy Center for Lake Champlain
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes




