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House vacation rentals in Whitingham

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Top-rated house rentals in Whitingham

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A bathroom features natural wood paneling and a brick accent wall. A compact vanity with a sink is complemented by a mirror and overhead lighting. Shelves hold neatly folded towels, while a washer and dryer unit is integrated into the design, presenting a functional space.

Home in Wilmington

4.91 out of 5 average rating, 232 reviews

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is also conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

A white cottage is framed by lush greenery and colorful flowers, including yellow irises and bluebells. Several large windows reflect sunlight, and a wooden bench sits invitingly among the vibrant plants, enhancing the serene garden setting.

Home in Townshend

4.97 out of 5 average rating, 126 reviews

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Top guest favorite

The cottage, constructed with a rustic red facade, is surrounded by vibrant greenery. A metal roof complements the structure, while nearby ferns and trees enhance the natural setting. Windows invite light into the space, showcasing a serene, wooded atmosphere.

Home in Guilford

4.96 out of 5 average rating, 131 reviews

Green River Cottage-A Peaceful Country Retreat

Bask in the beauty of rural Vermont while nestled in the woods of a cozy cottage along the Green River. Sit on the front deck and enjoy the sounds of the river or stargaze while surrounded by the enchanting beauty of the rolling emerald hills. Right outside the door you can walk, bike or jog for miles on quiet scenic back roads. Located on a dirt road 20 min. from Brattleboro & just a few miles from the Mass border, our cottage is the perfect place to relax or enjoy all the area has to offer.

A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.

Home in Whitingham

4.91 out of 5 average rating, 106 reviews

Vermont lake house near Mt. Snow-fab 360 views!

Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is just a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Top guest favorite

A inviting outdoor space features two blue Adirondack chairs paired with a fire pit, where flames reflect off colored glass. A hot tub is visible nearby, surrounded by greenery, enhancing the tranquil ambiance of the area.

Home in Wilmington

4.96 out of 5 average rating, 122 reviews

DowntownWilmington /HotTub-Firepit-OutdoorShower

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

A comfortable living area features a sectional gray sofa adorned with decorative pillows, a coffee table at the center, and two armchairs. Natural light filters in through large windows dressed in light curtains, illuminating the hardwood floor and creating a cozy atmosphere.

Home in Wilmington

4.88 out of 5 average rating, 180 reviews

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

Home in Winhall

4.96 out of 5 average rating, 274 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

A well-maintained home features a spacious porch with green chairs and is surrounded by a lush lawn and trees. The gravel driveway offers ample parking space, while the bright blue sky enhances the serene outdoor setting.

Home in Wilmington

4.94 out of 5 average rating, 285 reviews

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

The exterior of the home displays a charming red facade with light shutters and a welcoming front porch. An American flag is mounted next to the entrance. Lush trees and a blue sky create a natural backdrop, enhancing the home’s inviting presence.

Home in Wilmington

4.9 out of 5 average rating, 153 reviews

Family 4BR Cabin w/ Hot Tub & Pools – Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort & easy access to trails, lakes, and Wilmington’s shops & dining.

Top guest favorite

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.

Home in North Adams

4.99 out of 5 average rating, 136 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.

Home in Readsboro

4.86 out of 5 average rating, 128 reviews

Relax in Vermont! (Pet Friendly)

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked home. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, ski nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires, Bennington, Wilmington. Great location! PEACEFUL & PERFECT Vermont getaway! ☺

Top guest favorite

A charming two-story, red-paneled house features a welcoming front porch with white railings. Lush greenery and flowers line the stone walkway leading to the entrance, creating an inviting approach to the home.

Home in North Adams

4.98 out of 5 average rating, 462 reviews

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate. 10 min drive to Williams College & Clark. Steps to downtown & restaurants. Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

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Popular amenities for Whitingham house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

The farmhouse features a classic two-story white exterior with green shutters and multiple windows. Snow covers the ground in front, while the entrance is highlighted by a center door flanked by sidelights. A gentle landscape with shrubs is visible on either side.

4.98 out of 5 average rating, 198 reviews

Magical Farm Getaway - a must visit!

Home in Colrain

4.89 out of 5 average rating, 131 reviews

The 1770 House

Top guest favorite

The exterior of the industrial farmhouse is reflected in the calm water of the fishing pond. Surrounding vegetation includes lush green grass and reeds. The building features a warm glow from its windows, suggesting a welcoming atmosphere.

5 out of 5 average rating, 61 reviews

The Villa - Farmhouse with Hot Tub, Pool and Pond

Home in Deerfield

5 out of 5 average rating, 4 reviews

Serene South Deerfield Retreat

A spacious property is visible under a pastel sky at sunset, showcasing a well-maintained lawn with distinct stripes. The charming house, featuring a large covered porch, is framed by vibrant gardens and trees, with rolling hills visible in the background.

Home in Lanesborough

5 out of 5 average rating, 26 reviews

Mountain Blossom Retreat by Evergreen Home

Top guest favorite

The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.

4.98 out of 5 average rating, 58 reviews

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Top guest favorite

The exterior of the home is showcased, revealing a charming blend of rustic wooden shingles and modern design. Large windows and a stylish doorway invite natural light, while a stone foundation adds character. Lush grassy areas surround the house, enhancing its serene setting.

Home in East Chatham

5 out of 5 average rating, 20 reviews

Stylish Rural Sanctuary! (+ Summer Pool)

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

4.89 out of 5 average rating, 224 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Weekly house rentals

Top guest favorite

The exterior of a newly constructed wooden home is framed by greenery, with natural stone accents enhancing its rustic appeal. A spacious porch is adorned with potted plants, and large windows invite light into the inviting interior. Access to the upper level is provided by exterior stairs.

Home in Wilmington

5 out of 5 average rating, 11 reviews

New Construction Ski/Lake home

Top guest favorite

A spacious living room features a large sectional sofa with decorative pillows, paired with a wooden coffee table. Natural light floods in through large windows, highlighting the hardwood floor. The adjoining dining area, visible in the background, includes a wooden table surrounded by several chairs.

Home in Wilmington

4.96 out of 5 average rating, 57 reviews

Vermont Village Retreat Near Mount Snow

Top guest favorite

Aerial view of a charming home nestled among vibrant autumn foliage, showcasing rich reds and yellows. Rolling hills and a serene green field extend in the background, while a quiet road meanders through the picturesque landscape.

Home in Whitingham

5 out of 5 average rating, 68 reviews

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

The two-story cabin is nestled within a vibrant forest, showcasing a blend of green and autumn foliage. Warm light emanates from the windows, creating a cozy atmosphere against the backdrop of a cloudy sky.

Home in Wilmington

4.9 out of 5 average rating, 67 reviews

3 miles to Mt. Snow,4 Min to Hermitage w Hot Tub!

Top guest favorite

The exterior of the cottage is partially obscured by tall, colorful wildflowers swaying in the breeze. Sunlight illuminates the scene, highlighting the serene setting surrounded by greenery and trees, with a clear blue sky in the background.

Home in East Dover

5 out of 5 average rating, 56 reviews

Magical Retreat Cottage Autumn Colors & Waterfalls

The kitchen features modern cabinetry with a combination of dark and light finishes. A farmhouse sink is positioned beneath a window, complementing stainless steel appliances, including a gas range and dishwasher. A spacious countertop offers ample preparation area.

4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

4.93 out of 5 average rating, 68 reviews

Vermont Mirror House

Top guest favorite

Home in Whitingham

5 out of 5 average rating, 42 reviews

Stonehedge Farm family getaway - swim, ski, hike

Private house rentals

Top guest favorite

A two-story wooden house features a rustic facade with cedar shingles and a green metal roof. Large windows allow natural light into the interior. A wooden deck is accessible from the ground level, with chairs positioned on the grass nearby and a basketball hoop attached to the exterior.

Home in Charlemont

4.95 out of 5 average rating, 65 reviews

Tall Pines Rental

A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.

Home in Ashfield

4.97 out of 5 average rating, 69 reviews

An 18th century farmhouse

Top guest favorite

Home in Wilmington

5 out of 5 average rating, 34 reviews

Rustic home near skiing & lakes, walk to downtown

Top guest favorite

A green grassy area is framed by a large tree on the left, with a bird feeder standing amidst a variety of plants. In the background, expansive fields and rolling hills are visible under a partly cloudy sky, suggesting a serene rural environment.

Home in Stamford

5 out of 5 average rating, 40 reviews

Comfortable Entire Farmhouse close to North Adams

The cabin is set back from the winding gravel driveway, surrounded by lush green grass and trees. Brightly colored autumn foliage adds a touch of warmth against the rustic brick exterior and red roof. The peaceful atmosphere is enhanced by natural surroundings.

Home in Wilmington

4.85 out of 5 average rating, 93 reviews

Secluded cabin on brook near skiing and lakes

The exterior of the chalet features a two-story structure surrounded by greenery, with a spacious balcony on the upper level. Soft lighting outlines the balcony, creating a welcoming ambiance. A kayak is situated near the base of the chalet, indicating opportunities for outdoor activities.

Home in Wilmington

4.9 out of 5 average rating, 31 reviews

Newly renovated chalet, 9 min to Mt. Snow

Top guest favorite

A spacious yard is shown with a variety of trees, framed by a vibrant sunset sky. A comfortable seating area with chairs is positioned on the grass, offering views of the home and surrounding landscape, blending nature with the warm invitation of the evening.

Home in Bennington

5 out of 5 average rating, 26 reviews

VT at its best! - near museums, trails & colleges

4.87 out of 5 average rating, 55 reviews

Scenic mid-century chalet w/ hot tub near Mt Snow

Destinations to explore