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Places to stay near Naumkeag

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Top-rated vacation rentals near Naumkeag

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

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Top guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 468 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favorite
Tiny home in Tyringham
4.97 out of 5 average rating, 396 reviews

Enchanted Tiny Tower nestled in the Berkshires

Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

Guest favorite
A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.
Cottage in Becket
4.91 out of 5 average rating, 132 reviews

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Guest favorite
The spacious bedroom features a plush king-sized bed with high-end linens. A large rug covers the wooden floor, while accented walls create a modern atmosphere. A doorway leads to a bathroom, and additional furniture includes two gold-framed chairs and a desk beside a window.
Apartment in Great Barrington
4.87 out of 5 average rating, 147 reviews

King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Top guest favorite
A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.
Apartment in Stockbridge
4.96 out of 5 average rating, 119 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Guest favorite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Catskill
4.95 out of 5 average rating, 246 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Guest favorite
A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.
Guest suite in Richmond
4.93 out of 5 average rating, 198 reviews

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

Top guest favorite
A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.
Home in Kingston
4.98 out of 5 average rating, 175 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Guest favorite
A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.
Guesthouse in Stockbridge
4.9 out of 5 average rating, 152 reviews

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

Top guest favorite
Home in Lee
4.99 out of 5 average rating, 306 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Top guest favorite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 160 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Guest favorite
Tiny home in New Marlborough
4.94 out of 5 average rating, 168 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Popular amenities for vacation rentals near Naumkeag

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Naumkeag

Norman Rockwell Museum

474 locals recommend

Hancock Shaker Village

226 locals recommend

Mount Greylock

299 locals recommend

Naumkeag

181 locals recommend

Berkshire Botanical Garden

177 locals recommend

Berkshire Museum

142 locals recommend

Condo rentals with wifi

Guest favorite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Condo in Litchfield County
4.93 out of 5 average rating, 30 reviews

Meadow View

Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.94 out of 5 average rating, 71 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Superhost
A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.
Condo in Lenox
4.91 out of 5 average rating, 47 reviews

Spacious 3 bedroom apt in Lenox historic downtown

Superhost
A spacious light blue deck is shown, furnished with a small table and two white chairs. The surrounding area features greenery and a distant view of rolling hills, providing a serene outdoor space for relaxation.
Condo in Shelburne Falls
4.9 out of 5 average rating, 51 reviews

Flowers & Falls Spot House

Guest favorite
Condo in Albany
4.89 out of 5 average rating, 347 reviews

Elegant, spacious studio apt in historic mansion

Superhost
A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.
Condo in Kingston
4.89 out of 5 average rating, 171 reviews

walking distance to town and waterfront

Superhost
The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.
Condo in Hancock
4.61 out of 5 average rating, 162 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Superhost
Condo in Hartford
4.81 out of 5 average rating, 32 reviews

Newly Renovated Clean Comfortable Relaxing Ideal

Family-friendly house rentals

Top guest favorite
A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.
Home in Sheffield
4.99 out of 5 average rating, 129 reviews

Belle Meade

Top guest favorite
A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.
Home in Canton
4.99 out of 5 average rating, 131 reviews

Best River View, on Rail Trail in Collinsville!

Top guest favorite
A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.
Home in Lee
4.98 out of 5 average rating, 247 reviews

Berkshire 4 season home

Guest favorite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield
4.95 out of 5 average rating, 212 reviews

Cantabile life in the Berkshires

Guest favorite
An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.
Home in Stockbridge
4.94 out of 5 average rating, 155 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Top guest favorite
An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.
Home in Pownal
4.98 out of 5 average rating, 289 reviews

Cozy Vermont mini-house

Top guest favorite
A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.
Home in Stockbridge
4.9 out of 5 average rating, 117 reviews

Rabbit Run in the heart of Stockbridge Village

Guest favorite
Home in West Stockbridge
4.86 out of 5 average rating, 123 reviews

Peaceful Stockbridge Cabin in the Woods

Apartment rentals with air conditioning

Top guest favorite
A spacious bedroom features a wooden four-poster bed adorned with green and white pillows. A dining table with two chairs sits in one corner. Soft lighting is provided by a lamp and two hanging chandeliers, creating a calm ambiance.
Apartment in Hillsdale
4.98 out of 5 average rating, 244 reviews

Serene Suite: Hudson & Berkshires, Walk to Brewery

Guest favorite
A bright living area features a comfortable gray sofa complemented by colorful accent pillows. A black lounge chair sits beside a marble coffee table. Large windows allow plentiful natural light, and a sleek wood stove adds warmth to the space.
Apartment in Hudson
4.94 out of 5 average rating, 342 reviews

Romantic Warren St Penthouse w/Catskill Mtn Views

Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
4.99 out of 5 average rating, 188 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Top guest favorite
A wide expanse of green grass is framed by a line of trees under a blue sky dotted with fluffy white clouds. The landscape conveys a sense of open space and tranquility, characteristic of the surrounding rural setting.
Apartment in Plainfield
4.95 out of 5 average rating, 295 reviews

Sunny carriage house apartment

Guest favorite
A comfortable living area features a gray sofa adjacent to a wooden table and two chairs. Natural light filters through sheer curtains on the windows, highlighting the rustic wood flooring and a statement brick wall with a vintage-style light fixture above.
Apartment in Catskill
4.92 out of 5 average rating, 236 reviews

Catskill Village House - Garden Studio

Top guest favorite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Apartment in Coxsackie
4.99 out of 5 average rating, 154 reviews

Hudson River Beach House

Superhost
A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.
Apartment in Copake Falls
4.9 out of 5 average rating, 366 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Top guest favorite
A charming garden area is enclosed by a white picket fence, featuring an array of colorful flowers and tall sunflowers. The gray facade of the house provides a serene backdrop to the vibrant foliage, creating a welcoming atmosphere in the outdoor space.
Apartment in Conway
4.98 out of 5 average rating, 120 reviews

House Above the Hollow

Other great vacation rentals near Naumkeag

Top guest favorite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington
4.93 out of 5 average rating, 339 reviews

Artist Cottage

Guest favorite
The cozy Blue Jay Cottage features a vibrant blue exterior with white trim. A wooden porch with a railing leads to the entrance, surrounded by a mix of moss and bare trees. The landscape is softened by a light layer of snow, showcasing a serene countryside setting.
Guesthouse in Lee
4.95 out of 5 average rating, 22 reviews

The Blue Jay Cottage

Guest favorite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield
4.92 out of 5 average rating, 247 reviews

Peaceful Cabin in the Woods

Guest favorite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
Cottage in Saugerties
4.94 out of 5 average rating, 365 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Guest favorite
A cozy living area features a brown leather sofa with white throw pillows, positioned beside a window that allows natural light. A wooden coffee table sits atop a blue and white woven rug, complemented by a comfortable armchair. Shelves display decorative items and fresh flowers add a welcoming touch.
Cabin in Litchfield County
4.93 out of 5 average rating, 135 reviews

Blackberry Cottage

Top guest favorite
Home in Germantown
4.95 out of 5 average rating, 485 reviews

Rustic Swedish Barn/Featured in Airbnb Magazine

Guest favorite
The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.
Treehouse in New Marlborough
4.9 out of 5 average rating, 154 reviews

Berkshire Treehouse Retreat

Top guest favorite
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 120 reviews

Mountain Retreat close to Northampton & Amherst!

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