Vacation rentals in Pittsfield

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

This home was built in 2020 with the beautiful lake and mountain views in mind. The Wild Loon is what we decided to name our retreat because we are often visited by wild loons here on the lake. The Wild Loon has an open concept floor plan. Sleeping arrangements are upstairs and downstairs in the basement. The half bath, kitchen, living and dining room are all on the main floor. Parking is directly across the road and can fit 4 vehicles in the summer, spring and fall 3 vehicles during winter

5 out of 5 average rating, 5 reviews

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

4.89 out of 5 average rating, 9 reviews

A grassy area features a fire pit surrounded by several white Adirondack chairs. A large tree provides shade beside the inviting white house, which has multiple windows and a porch. Scenic views of the landscape are visible in the background.

Home in Poultney

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

4.92 out of 5 average rating, 171 reviews

A cozy bedroom features a wooden bed with a light-colored comforter and decorative pillows. A subtle grey blanket is neatly rolled on the bed. A dresser and a TV are positioned against the wall, with a bedside lamp providing soft lighting, complemented by natural light from a nearby window.

Cottage in Fair Haven

Historic Cottage 2 Bedroom 2 Bath Fast Wifi

Ski season has begun! Picturesque cottage next to the Castleton River. You can wake up to the birds chirping and fall asleep to the frogs croaking. Hourly church bells ring throughout the day. Walk down the historic slate sidewalk to the park and local beer, pastries & the best diner! Minutes to many lakes, trails & mountain activities. Perfect for day trips to Killington, Okemo, Woodstock, Lake George, Vergennes, Rutland, Burlington & Saratoga Springs. Message us about seasonal discounts!

4.95 out of 5 average rating, 20 reviews

A warm entryway reveals an open living space, featuring wood floors and a vaulted ceiling with exposed beams. A modern dining table can be seen in the distance, accentuated by a large decorative wall piece. Natural light fills the area, enhancing the inviting atmosphere.

Condo in Warren

Charming Sugarbush Farmhouse Condo with Hot Tub

MRT-11088676 The Mad House used to house the most exclusive restaurant in the valley. After a million dollar renovation it has transformed from the Common Man restaurant into the Mad House Rentals. This professionally managed, Renovated barn is nestled between Lincoln Peak and Mount Ellen, with Mad River Glen just a short distance away. The Mad House brings you everything you could want for any season. Ski lockers, mudrooms, A/C in most units, private decks with private grills and hot

4.96 out of 5 average rating, 149 reviews

A cozy interior is showcased, featuring a classic fieldstone fireplace with a mounted smart TV above it. Two pendant lights illuminate the room. A green armchair offers seating, along with a small kitchen area visible in the background.

Cabin in Plainfield

Magical cabin with amazing views

100 year old , freshly renovated cabin that is in the middle of five 100 year old apple trees with incredible Mountain View’s. The cabin sits 100ft uphill from my 1842 brick farmhouse and is surrounded by apples trees, an ancient elm tree, fields and my berry patches. The huge deck has a dining table, lots of seating and and outdoor shower. Off the side of the deck are two claw foot bathtubs with hot and cold water for you to soak in. Note, tubs aren’t usable during the freezing months.

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.97 out of 5 average rating, 33 reviews

A modern kitchen features wood cabinetry and stainless steel appliances. A polished countertop provides ample workspace, while a multiple-burner stove and microwave cater to cooking needs. Natural light enhances the room through a nearby window, complemented by patterned curtains. A trash can and sink are also visible.

Apartment in Pittsford

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

4.96 out of 5 average rating, 225 reviews

A spacious wooden house features a balcony with a railing, overlooking a green lawn. Large windows allow natural light to fill the interior, while five skylights add brightness. Vibrant trees display autumn foliage in the surroundings, creating a serene atmosphere.

Home in Addison

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!

4.96 out of 5 average rating, 26 reviews

The kitchen features a modern design with white cabinetry and a wooden countertop. Two windows allow natural light to brighten the space, while stainless steel appliances, including an oven, are positioned along the walls. A sink is centrally located, enhancing functionality.

Home in Cavendish

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

4.78 out of 5 average rating, 9 reviews

Apartment in Warren

Professionally Managed Ski Gem

New listing! Come de-stress in the beautiful mountains of Vermont. Our condo and all the amenities included are perfect for a romantic getaway or a family vacation. Located less than a half mile from Sugarbush Resort, our condo is an ideal location for a ski vacation. However, the access to 3 pools, 2 hot tubs, tennis courts, basketball court, gym and more make this a perfect 4 season rental as well!

4.8 out of 5 average rating, 10 reviews

A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.

Home in Hartford

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access

0 of 0 items showing

What guests are saying

Highland Haus: stunning ski getaway with hot tub

5 out of 5 average rating, 10 reviews1 month ago

Beautiful home that is about 15min from Manchester, which is wonderful to walk around (shops, restaurants). The home is secluded on a nice piece of property in the woods. It was a charming getaway with a wood-burning fireplace and great amenities (games, dart board, hot tub, etc). Highly recommend!

Home in Peru

What guests are saying

Breathtaking Southern Views of Lake George

4.91 out of 5 average rating, 66 reviews8 months ago

Absolutely beautiful spot on the lake! The house was perfect for our extended family (grandparents, parents and children) and extremely clean. I am usually a tough critic of cleanliness of air bnbs and very nose sensitive. Besides cobwebs (outside!) the entire place was spotless and odor free! Plenty of towels for the entire family and comfy beds and linens. Honestly felt like a home away from home. We brought our boat and explored the northern quarter of the lake. The dock looked brand new. A very nice sandbar on the opposite side of the island seen from the dock- great to park and swim at. Lots of cool islands to explore nearby too. It unfortunately rained almost every day we were there so thank god the house was big enough and comfy for 6 adults and 2 kids to hang out. Would recommend it to anyone looking for a peaceful part of lake George

Home in Ticonderoga

What guests are saying

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

4.98 out of 5 average rating, 48 reviews1 month ago

Awesome place! All the games in the basement gave us something to do while hanging inside the house. It’s great being able to come back after a long day of snowboarding and relaxing in the hot tub. The kitchen had everything we needed to cook. Only thing “negative” I could say is we couldn’t find any trash bags for the trash cans but obviously not that big of a deal. Overall I would 100% recommend and would definitely stay here again, without a doubt

Home in Cavendish

What guests are saying

Private post & beam log cabin on Macintosh Pond.

4.8 out of 5 average rating, 15 reviews3 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

Cabin in Barnard

What guests are saying

Comfortable Vermont Getaway. Three bedroom home.

4.93 out of 5 average rating, 14 reviews2 months ago

Robyn and her family are great hosts. She and her son were there when we arrived shoveling the drive way, gave us some helpful tips about the house, very friendly and accommodating - we were able to check in a couple of hours early and really made us feel right at home. Beautiful house with all amenities: Kitchen had everything would need to cook for several days (pots, pans, utensils, glass/coffee mugs, and even provided coffee and filters) - we only needed to bring food to prepare. Stores were close by and easy to get to. Bathrooms were pristine with plenty of towels and toiletries, bedrooms were spotless and comfortable, and had a great fireplace that was very useful during some cold days. About 15-20 minutes to Killington Mountain - easy drive. Fantastic property and we had an amazing stay, would definitely come back!

Home in Rutland

What guests are saying

The Carol

5 out of 5 average rating, 22 reviews1 month ago

The Carol is a stunning and beautifully decorated historic home that was the perfect getaway for our ski trip!!! We stayed one night but wish we had stayed longer! It is located only 10 mins from Okemo which was perfect. The beds were super comfy and the bathroom and kitchen were stocked with everything we needed. Sarah was super helpful and responsive to everything and provided tons of recommendations to make our stay worthwhile. Would 100% recommend this place to anyone looking to ski Okemo!

Home in Cavendish

What guests are saying

A quiet x in VT to Ski, Hike, Hot tub~3m Quechee

4.92 out of 5 average rating, 12 reviews2 months ago

I visited Thatcher and Lisa's place for a few days in February with 5 friends. It was an incredible experience overall. The home was a perfect peaceful getaway, with awesome amenities like multiple private rooms, a well-stocked kitchen, hot tub, and games. It is also very nicely located, providing a peaceful rural setting while also having great access to nearby areas like Woodstock, Hanover, and Killington (where we spent ~3 days skiing). Additionally, Lisa and Thatcher really went above and beyond as hosts. They left very clear instructions and recommendations, made sure that we arrived smoothly in the face of inclement weather, and even shipped home an item we left behind. I definitely recommend staying here for your next Vermont adventure!

Home in Hartland

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Pittsfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend

Original General Store20 locals recommend

Vermont River Tubing16 locals recommend

Green Mountain Trails16 locals recommend

The Backroom14 locals recommend

White River Golf Course11 locals recommend

Other great vacation rentals in Pittsfield

5 out of 5 average rating, 12 reviews

A wooden railing frames the outdoor balcony, offering views of the calm lake. Sunlight glimmers on the water's surface, with green hills visible in the background. A few boats are moored nearby, and the scene conveys a serene outdoor environment.

Home in Wells

Breathtaking Lakeside Retreat!

4.75 out of 5 average rating, 92 reviews

An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.

Condo in Killington

Still 89 Trails Open, Low, Low Rates

5 out of 5 average rating, 8 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

5 out of 5 average rating, 16 reviews

A spacious kitchen and dining area is seen, featuring a large granite island with bar seating. Open shelving and modern appliances are present. A staircase with wooden steps and metal railings leads to the upper level, while large windows invite natural light into the room.

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

4.97 out of 5 average rating, 39 reviews

A spacious hot tub emits a soft blue glow in the dark, surrounded by mist. The area is accented with a wooden deck, and a staircase provides access to the tub. Soft lighting enhances the peaceful ambiance of the outdoor space.

Home in Warren

Private Home with Hot Tub 1 mile from Sugarbush

4.93 out of 5 average rating, 57 reviews

Home in Newport

Crescent Lake home swim, golf and hike

4.96 out of 5 average rating, 27 reviews

An indoor pool area features large windows that bring in natural light, showcasing winter scenery outside. Comfortable lounge chairs and a table with an umbrella are arranged around the pool, creating a serene space for relaxation.

Condo in Killington

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC