We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Holiday houses in Pittsfield

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Chalet in Stockbridge

4.85 out of 5 average rating, 114 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

24 – 31 Aug

$1,934 AUD total

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 131 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

10 – 17 Aug

$1,315 AUD total

Guest favourite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 reviews

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. 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.

3 – 10 July

$1,512 AUD total

Guest favourite

Apartment in Chittenden

5.0 out of 5 average rating, 223 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont. * We are following the guidelines set up by the W.H. O. and we are leaving a window between reservations to disinfect our suite due to Covid-19.

25 Feb – 4 Mar

$1,678 AUD total

Guest favourite

Apartment in Pittsford

4.99 out of 5 average rating, 118 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike in the warmer weather. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

7 – 14 July

$1,286 AUD total

Guest favourite

Guest suite in Bethel

4.97 out of 5 average rating, 137 reviews

Two bedroom. Separate enterence.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

4 – 11 Sept

$1,602 AUD total

Guest favourite

Home in Rochester

4.97 out of 5 average rating, 182 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!

22 – 29 Aug

$2,005 AUD total

Guest favourite

Home in Pittsfield

4.91 out of 5 average rating, 149 reviews

Beautiful Mountain Log Cabin with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from killington and pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

14 – 21 July

$4,621 AUD total

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 394 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

13 – 20 Mar

$1,676 AUD total

Guest favourite

Tiny home in Warren

4.99 out of 5 average rating, 154 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet.

16 – 23 Oct

$8,770 AUD total

Guest favourite

Apartment in Rutland

4.96 out of 5 average rating, 525 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

20 – 27 July

$1,145 AUD total

Guest favourite

Apartment in Hancock

4.95 out of 5 average rating, 146 reviews

Suite in the Green Mountains

We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette, a bedroom with queen bed, and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

31 Aug – 7 Sept

$1,156 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Pittsfield holiday rentals

Free parking on premises

Air conditioning

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend

Clear River Inn9 locals recommend

Swiss Farm Inn10 locals recommend

Green Mountain Trails16 locals recommend

Riverside Farm3 locals recommend

The Backroom14 locals recommend

Other great holiday rentals in Pittsfield

Guest favourite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

4 – 11 Dec

$1,854 AUD total

Guest favourite

Condo in Killington

4.89 out of 5 average rating, 204 reviews

Killington-Pico ski in/out Studio at base of Pico

4 – 11 July

$1,301 AUD total

Guest favourite

Home in Bethel

4.85 out of 5 average rating, 130 reviews

Hike, run, swim or cycle in beautiful Central VT

21 – 28 Aug

$1,510 AUD total

Guest favourite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

17 – 24 May

$1,204 AUD total

Guest favourite

Guest suite in Royalton

4.96 out of 5 average rating, 180 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

23 – 30 July

$1,499 AUD total

Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 221 reviews

Hancock hideaway

10 – 17 May

$1,854 AUD total

Guest favourite

Home in Killington

4.92 out of 5 average rating, 165 reviews

Cozy Condo Tucked in the Heart of Killington

6 – 13 June

$1,853 AUD total

Guest favourite

Home in Middlebury

4.99 out of 5 average rating, 355 reviews

Nice one bedroom cottage

6 – 13 Nov

$1,556 AUD total

Quick stats about holiday rentals in Pittsfield

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
$182 AUD before taxes and fees

Destinations to explore