Holiday houses in Pittsfield

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Top-rated holiday rentals in Pittsfield

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Top Guest favourite

Tiny home in Castleton

4.99 out of 5 average rating, 107 reviews

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Top Guest favourite

Guest suite in Stockbridge

5 out of 5 average rating, 100 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Top Guest favourite

Yurt in Randolph

5 out of 5 average rating, 130 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Top Guest favourite

Cabin in Stockbridge

4.95 out of 5 average rating, 110 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Guest favourite

Treehouse in Hancock

4.97 out of 5 average rating, 119 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

Guest favourite

Cabin in Pittsfield

4.98 out of 5 average rating, 157 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Superhost

Home in Pittsfield

4.91 out of 5 average rating, 171 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.

Guest favourite

Chalet in Stockbridge

4.96 out of 5 average rating, 128 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 474 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.

Top Guest favourite

Apartment in Rutland

4.96 out of 5 average rating, 610 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, skiing, golf, 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.

Top Guest favourite

Condo in Killington

4.99 out of 5 average rating, 113 reviews

Cozy Condo next to Resort * AC and Pool *

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! King bed and Queen pullout sofa sleeps up to four (4). This property is Shuttle In/Out (Sat & Sun and holiday periods Dec - April). Killington Reg #004858

Guest favourite

Treehouse in Bethel

4.98 out of 5 average rating, 109 reviews

Crooked Maple Treehouse

Nestled in the heart of the Vermont Green Mountains, the Crooked Maple Treehouse is handcrafted from timber harvested and milled on-site by the owner, Brett. Thoughtfully crafted to create a rustic and cozy retreat. Take this opportunity to escape your busy everyday life to appreciate the simplicity and solitude of living off the grid at the Crooked Maple.

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Other great holiday rentals in Pittsfield

Top Guest favourite

Apartment in Rochester

4.94 out of 5 average rating, 48 reviews

Cozy Green Mountain Village Apt

RyanRating, 5 stars2 weeks ago

Was in need of a place to stay in Rochester for a wedding down the road from the main part of town and I couldn't have picked a better spot for the weekend. It's a cozy little apartment that has all the simple things you need and it's walking distance to some small town jems to shop and eat at. If I ever want to come back to VT from Boston for the fall, or to escape the city life, I know what would be my first pick would be. :)

Superhost

Cabin in Stockbridge

4.91 out of 5 average rating, 45 reviews

Stunning Artist Retreat Cabin

KatelynRating, 5 stars3 weeks ago

Such a cute, unique cabin! It has inspired me to maybe build one back at home! We especially loved the tiny fireplace, seeing the stars from the loft, and the frog music. Only note for future guests is to make sure to read the full description as she notes that the Internet is spotty and didn't work the entire stay for us.

Guest favourite

Cabin in Bethel

4.95 out of 5 average rating, 80 reviews

The Gourmet Cabin at Stitchdown Farm

CorrielleRating, 5 stars4 weeks ago

Holy Smokes! So so peaceful and beautiful! My favorite was falling asleep (in the extremely comfortable bed) to frog sounds. Plenty of books and wonderful nearby hikes. We bought some maple syrup flower sprinkles from the farm stand on the property for gifts. The nearby town is lovely with a great family oriented bar called Babes. Would definately stay again!

Top Guest favourite

Tiny home in Pittsfield

5 out of 5 average rating, 39 reviews

Tiny Home: VT Mountain Cabin

AveryRating, 5 stars8 months ago

Great host, great location. Place is beautiful and definitely worth the trip!

Superhost

Home in Pittsfield

4.83 out of 5 average rating, 78 reviews

Green Mountain/Killington Getaway

ErnieRating, 5 stars3 months ago

Six of us stayed four nights in March at Paula’s place. Everything was great. Of the ones that stayed in the bunks all agreed we slept great. Usually bunks are uncomfortable but it was nice here. We aren’t small either. The house had everything we needed and was close enough to the mountain. We had two days of good snowboarding. The access road to the house isn’t great but we all made it fine with a civic, X3, and F150. We would all stay here again. Paula is a great host.

Top Guest favourite

Chalet in Killington

4.99 out of 5 average rating, 70 reviews

The Overlook - AC | Hot Tub | View | Fires | Games

KevinRating, 5 stars1 month ago

Oh my God the views! Super cute place with plenty of room and awesome hosts. The hot tub is nice (but SUPER chlorinated, which was a little annoying, but I get it). The kitchen is STOCKED with gadgets and cookware, which is super convenient. Also, killer location: great restaurants less than a mile away in Killington village and Rutland only 20 min away. Everything was clean and tidy and the whole family had an absolute blast. Will definitely come back.

Guest favourite

Home in Pittsfield

5 out of 5 average rating, 40 reviews

Hike & MTB In/Out Golf & Swim 2 Living Rooms

DanielleRating, 5 stars2 months ago

We loved our stay at Ed’s place, came with a group of friends to go skiing at Killington for the weekend. We had an issue with the power downstairs and wifi but Ed was very accommodating and responsive. The place matches the photo/description - this place is a gem!

Guest favourite