House holiday rentals in Chittenden

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Top-rated house rentals in Chittenden

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Guest favourite

Home in Barnard

4.99 out of 5 average rating, 152 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Top guest favourite

Home in Tunbridge

4.98 out of 5 average rating, 403 reviews

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

Superhost

Home in Rutland

4.81 out of 5 average rating, 160 reviews

6 Bedroom Home Mendon, VT. (Killington/Pico)

Relax with the whole family or multi families at this peaceful Mountain side retreat in Mendon Vermont. 5 min drive to Pico Ski Resort. 10 min drive to Killington. Great views and sunsets. Driving distance to downtown dinning or apre ski. The House is split into two separate apartments. This is one home but the two apartments are not connected inside and would require access to the other apartment from the Exterior/outside entrance. Great internet WIFi. Speed: Up to 150Mbps Security: WPA2-AES

Guest favourite

Home in Salisbury

4.95 out of 5 average rating, 111 reviews

Picture Perfect Lake Dumore Home

Located directly on Lake Dunmore, our home is the perfect house to catch the sun glistening on the lake. With 2 bedrooms, it can comfortably sleep up to 2 families of 4, easily split between the upper and lower level with the main/deck level in between. Tons of family fun to be had: pool table, foosball, hot tub, games/toys, stocked kitchen, a deck and dock overlooking the pristine mountain lake and minutes to Branbury State Park's Beach. Nay's Lake House has mini split cooling and heating.

Top guest favourite

Home in Killington

4.93 out of 5 average rating, 117 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

Superhost

Home in Rochester

4.91 out of 5 average rating, 298 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.

Guest favourite

Home in Rochester

4.96 out of 5 average rating, 156 reviews

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Guest favourite

Home in Rochester

4.97 out of 5 average rating, 208 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Guest favourite

Home in Pittsfield

4.85 out of 5 average rating, 107 reviews

A million-dollar view near Killington on 60 acres.

This secluded 200 + year old mountain farmhouse is located in the small town of Pittsfield, VT just 5 minutes away from one of the most scenic drives in New England, Route 100. Surrounded by national forest with stunning views of the Green Mountains, this is the perfect place to get away with family or even by yourself. Plenty of room outside on the 60+ acre property with fields and a small pond. In the center of Vermont, it's the perfect home base.

Top guest favourite

Home in Rutland

5 out of 5 average rating, 138 reviews

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

Guest favourite

Home in Pittsfield

4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Guest favourite

Home in Pittsford

4.94 out of 5 average rating, 200 reviews

Colburn's Carriage House

Only 30 minutes from Killington/Pico ski resorts, and 20 minutes from Mountain Top Inn and Chittenden Reservoir, Colburn's Carriage House is a charming and convenient getaway. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.