Family-friendly holiday rentals in Middlesex

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Top-rated family-friendly rentals in Middlesex

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Waitsfield

4.96 out of 5 average rating, 140 reviews

Warm Luxury Mid-Century Modern Chalet

Warm, clean & comfortable chalet w/ thoughtful & stylish touches. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swim holes, farms, hiking, road & mtn bike, golf, climbing, tube on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views of surrounding mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

Guest favourite

Guest suite in Burlington

4.92 out of 5 average rating, 382 reviews

3 Cozy Rooms ,2 Bathrooms,2 Bedrooms,Beach,Bike

This quiet, charming neighborhood is a treasure. Lake Champlain , on the 14 mile bike path. Bikes available. microwave, small fridge, toaster oven, Keurig coffeemaker provided, Wifi, HD Smart TV, Netflix , Amazon Prime, DVD, Roku, HuluTV, CD player, screened in front porch. Locking gate at the top of the stairs.There is not a kitchen. Not recommended for guests who what to cook. Two bedrooms one full bath and one half bath. LGBTQ always welcome. Well behaved doggie parents and dogs allowed.

Guest favourite

Home in Rutland

4.81 out of 5 average rating, 347 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Guest favourite

Home in Rochester

4.91 out of 5 average rating, 295 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Top Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 180 reviews

Close to Smuggler's Notch Resort! High speed Wifi!

NOTE: Minimum age of 25 years required to rent our house and to be a guest here. Children traveling with parents are exempt from this age requirement. Exceptions made on a case by case basis. Beautiful, bright, and spacious 4 bedroom home in the heart of Smuggler's Notch area with views of the mountains. Less than 4 miles to Smugglers Notch Resort and 1 mile from the Wedding Barn. Property consists of our primary residence with the rental being a separate and private "mother in law" home.

Guest favourite

Cabin in Barton

4.81 out of 5 average rating, 159 reviews

Charming lake cottage on Crystal Lake! Boats! R&R!

Lakeview Cottage is adorable and located on one of Vermont's cleanest and most beautiful lakes, Crystal Lake! It's in the heart of the Northeast Kingdom, in the charming town of Barton. Sit around the outdoor firepit and soak in the view! You're just steps away from beaches and a dock. You'll find great swimming, fishing, boating, hiking, golfing, and mountain biking. Use our canoe or kayaks! Plus, Hill Farmstead Brewery is a short drive away. Beers there are rated best in the world!

Top Guest favourite

Cabin in Hyde Park

4.96 out of 5 average rating, 278 reviews

Serene Country Cabins 2 In the heart of Vermont

My place is close to Stowe, Smuggler's Notch and within 15 minutes of 6 breweries. It is nestled in the woods with some views, art and culture, farms, hiking trails, lakes, 3 major ski resorts, snow machine trails, and 3 miles from the down town shopping plazas. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Our bedrooms offer a create a king to accommodate guests who prefer a king bed and guests who prefer twin beds.

Guest favourite

Cabin in Jeffersonville

4.93 out of 5 average rating, 191 reviews

Cozy two-bedroom cabin near Smugglers Notch

Our two-bedroom log cabins (we have several) are a long-time family and small group favorite. Equipped with one queen bed, two twin beds (that can be converted to a king), one bath, a kitchen, living space, a woodstove or traditional fireplace, TV, and free WiFi, these cabins are cozy, yet spacious enough for the whole family or two couples to enjoy. This cabin has a maximum occupancy of 6 adults/children. Close to skiing/snowboarding, hiking, horseback riding, wedding barns and more.

Top Guest favourite

Home in Addison

4.96 out of 5 average rating, 225 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Guest favourite

Condo in Killington

4.78 out of 5 average rating, 176 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Killington has become a wonderful 4 season resort area that satisfies many tastes. You can hike, play golf ,swim, bike, ski-snowboard, or just lay back and enjoy the surroundings. You can go to the Killington website to find out what is happening. Please go to the Killington website to get complete information before you go. There is also a Mountain Green website that will let you know which amenities are available during your stay. mountaingreen.com

Guest favourite

Townhouse in Stowe

4.89 out of 5 average rating, 167 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

Superhost

Home in Stowe

4.83 out of 5 average rating, 161 reviews

Great For Large Groups with Hot Tub

This property is not suited to noisy groups - please don’t book for partying. Recently renovated to meet every vacation need, this unique property has everything you require for a great trip. The property is huge, ideally located right on Mountain Rd - minutes to slopes, spas, breweries, restaurants, hiking, biking and swimming holes. With 4 large comfortable bedrooms, fun basement, huge living space with fireplace and private hot tub.