Holiday rentals with a fireplace in Pittsfield

Guest suite in Lake Bomoseen

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

4.97 out of 5 average rating, 237 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

4.94 out of 5 average rating, 131 reviews

Treehouse in Stockbridge

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

4.99 out of 5 average rating, 136 reviews

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

Apartment in Killington

Elegant Alpine Condo

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Killington Reg #007718

4.97 out of 5 average rating, 113 reviews

A vibrant garden features an array of yellow daffodils and blooming flowers, extending towards the grassy area. In the background, a charming cottage with a brown roof is nestled among lush trees under a clear blue sky, creating a serene country setting.

Cottage in Tunbridge

Vermont Hillside Garden Cottage

Cozy converted artists’ studio, tucked in the hills at the end of a country road. Open the French door to views of a sprawling garden and rolling fields, alight with fireflies in the spring and bursting with color in the fall. Warm yourself by the wood burning stove after winter fun or unwind with a local microbrew by the fire pit, listening to the Whippoorwills on a summer evening. Beautiful in all seasons, this modern, comfy cottage is the perfect place to get away from it all.

4.97 out of 5 average rating, 432 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Earthen home in Granville

A serene winter landscape features three charming structures nestled among snow-covered trees. The main yurt and the smaller yurt are joined by a wooden cabin, all adorned with a soft layer of snow, creating a peaceful retreat in a forested setting.

4.93 out of 5 average rating, 152 reviews

Sculpted Earthen Yurt Near World Class Skiing

Secluded winter wonderland near Vermont's best skiing! Enjoy a 25-acre mountain homestead all to yourself, w/two beautifully-appointed yurts & a cabin. Toasty warm sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Stargaze around the fire circle under a glittering dark sky. A winter paradise for downhill & XC skiers; a haven for digital nomads, writers, & creatives; a refuge of deep quiet. Between Sugarbush, Mad River Glen, & Snow Bowl.

4.9 out of 5 average rating, 156 reviews

The exterior of the Austrian-style home is blanketed in fresh snow, highlighting its unique architectural features. Ice-tinged trees surround the property, while the American flag is prominently displayed. A serene mountain backdrop completes the winter landscape.

Flat in Killington

Killington VT Chalet - Lower apartment

Entire lower apt of Austrian Style home in Killington across from Pico Mtn offers beautiful views in a quiet setting with preserved forest and the Appalachian & Long Trail in our backyard. Only 2 miles to Killington Access Road. The apartment is the lower unit, owners occupy the upper unit. We are a ski family and are up early each morning. Previous reviews REQUIRED, no 3rd-party bookings. No partiers, smokers, or loud gatherings. No pets including service animals.

4.92 out of 5 average rating, 110 reviews

An aerial view captures the snow-covered Pico Mountain with ski trails visible on the slopes. The surrounding trees are dusted with snow. The Village Square at Pico Condo Association is seen at the base, with buildings arranged neatly alongside a parking area.

Apartment in Killington

Ski-on/ski-off 3BR at base of Pico Mountain!

Ski-on/Ski-off!! Our condo is at the base of Pico Mountain and offers amazing views from the private balcony. Enjoy all the benefits of being slope side of Pico Mountain while just 10 minutes away from Killington Resort! Pico Mountain offers 57 trails with 6 lifts and is a family-favorite to avoid some of the weekend crowds at Killington. Less then 1 mile from the Long Trail and Deer Leap overlook hiking trail. Both fantastic must-do hikes when in the area!

4.86 out of 5 average rating, 111 reviews

An aerial view highlights a secluded mountain farmhouse surrounded by lush greenery and rolling hills. The expansive 60+ acre property features a blend of fields and forests, with the distant Green Mountains visible under a partly cloudy sky.

Home in Pittsfield

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.

4.93 out of 5 average rating, 194 reviews

A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.

Chalet in Royalton

Scandinavian design Chalet w/ private hiking trail

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

4.97 out of 5 average rating, 150 reviews

A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.

Chalet in Stockbridge

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.

4.96 out of 5 average rating, 132 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Popular amenities for rentals with a fireplace in Pittsfield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

4.96 out of 5 average rating, 548 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

Cozy Bow House Perched in Trees w/ Hot Tub & View

4.87 out of 5 average rating, 150 reviews

A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.

Home in Stockbridge

Escape to Vermont

4.92 out of 5 average rating, 223 reviews

A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.

Home in Roxbury

Captain Tom's Cabin - Secluded Vermont Getaway

4.91 out of 5 average rating, 105 reviews

A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.

Home in Killington

Ski home to Trail Creek!

4.98 out of 5 average rating, 436 reviews

A unique house constructed from reclaimed wood features a distinctive round shape and a metal roof. The natural stone fireplace is visible on one side, while large windows allow for ample light and views of the surrounding greenery.

Home in Tunbridge

The Barnbrook House

4.97 out of 5 average rating, 105 reviews

A log cabin with a spacious deck, constructed from natural wood, is set against a backdrop of bare trees and mountains. The exterior features large windows and a chimney, allowing for natural light and warmth. Shadows from the trees add depth to the grassy area in front.

Home

Secluded Log Cabin with Unrivaled Views!

4.97 out of 5 average rating, 180 reviews

The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.

Home in Middlebury

Purple Door Cottage in the heart of Middlebury!

4.97 out of 5 average rating, 149 reviews

A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.

Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

Apartment rentals with a fireplace

5 out of 5 average rating, 211 reviews

A bright living area features tall windows allowing natural light to fill the space. A comfortable white sofa, accent chairs, and a wooden coffee table are positioned on warm wooden flooring. A bookshelf with numerous books adds character, while a desk provides a workspace.

Flat in Middlebury

The Barn at Middlebury

4.95 out of 5 average rating, 106 reviews

A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.

Flat in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

4.98 out of 5 average rating, 121 reviews

A spacious living room is depicted featuring comfortable sofas and a stylish coffee table. Natural light enters through a window with dark curtains, while a decorative rug adds warmth to the wood floor. A welcoming entryway is visible in the background.

Flat in Middlebury

Spacious Home Near Heart of Middlebury Fiber Wifi

5 out of 5 average rating, 259 reviews

A flowing waterfall cascades over rocky terrain, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. The water splashes against large stones, while vibrant foliage frames the scene.

Flat in New Haven

Dog Team Falls Apartment - Minutes from Middlebury

4.92 out of 5 average rating, 180 reviews

Flat in Plymouth

Canyons Unit: Skyeship Gondola 2 miles w/HOT TUB

Flat in Middletown Springs

The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.

4.89 out of 5 average rating, 272 reviews

Apartment in Vermont Historic Home

4.9 out of 5 average rating, 196 reviews

A charming two-story lake house apartment features a welcoming exterior with a covered porch adorned with hanging plants. Bright sunlit spaces are framed by large windows, and a grassy area is visible in the foreground, enhancing the outdoor ambiance.

Flat in Salisbury

Doc's Lake House 1st floor, 2 bdrm full apartment

4.99 out of 5 average rating, 167 reviews

A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.

Flat in Middlebury

Bluebird Studio- Light filled and airy

Villa rentals with a fireplace

5 out of 5 average rating, 26 reviews

A modern ceiling fan with five black blades is centered above a spacious living area, featuring two large skylights that allow natural light to fill the room. Tall windows frame the outside view, bringing the beauty of the outdoors inside.

Villa in Warren

Cozy, Comfy & Sunny renovated Sugarbush condo

4.9 out of 5 average rating, 40 reviews

The Windsor Mansion is positioned at the top of a hillside, surrounded by a lush landscape of trees in various shades of green and hints of autumn colors. The elegant white of the mansion’s exterior contrasts with the natural setting, creating a striking visual.

Private room in Windsor

Private Wing of largest Colonial Mansion in US

5 out of 5 average rating, 3 reviews

The living area features a comfortable blue sofa paired with a cozy armchair, illuminated by warm table lamps. A wooden coffee table sits at the center, and large windows with blue drapes provide a view of the surrounding landscape, creating a welcoming atmosphere.

Villa in Rutland

Pico D305 located slope side at Pico quiet area

A cozy living area is enhanced by a large brick fireplace. Two plaid sofas face each other, complemented by a wooden coffee table in the center. A large window allows natural light to fill the space, framed by blue curtains and adorned with seasonal decor.

5 out of 5 average rating, 3 reviews

Sunrise East Glade C8 Ski on Ski off

A comfortable living area is furnished with a spacious sofa and a wooden coffee table. Natural light floods the room through large windows, providing views of the outdoors. Artwork is displayed on the walls, while a lamp adds subtle illumination beside the seating.

4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7 Ski on Ski off

4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

The exterior view showcases an inviting multi-unit building with a unique architectural design. Angled roofs and large windows create an airy feel, while well-kept landscaping and gravel pathways enhance the property’s natural setting.

Whiffletree base of Killington outdoor pool

A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.