Holiday rentals with breakfast in Lenox

4.93 out of 5 average rating, 222 reviews

A spacious bedroom features floral wallpaper with green and pink patterns. A wooden bed is draped with a red patterned coverlet and accented by a decorative pillow. Two windows allow for natural light, and a bedside table with a lamp complements a nearby chair.

Flat in Athens

1 bdrm apt in Athens on the Hudson

Come enjoy village life right in the middle of this friendly and vibrant, yet quiet community in your own charmingly appointed 3 room apartment. Explore the Great Northern Catskills with its boating and paddling opportunities, antiquing, local history, art and music. The Thomas Cole House is minutes away in Catskill. Olana is right across the Rip Van Winkle Bridge. If sculpture is your passion, Opus 40 in Saugerties is not to be missed. Winerys abound and be sure not to miss Athens own brewery.

Guest house in North Adams

A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.

5 out of 5 average rating, 298 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

4.95 out of 5 average rating, 356 reviews

Adirondack chairs are positioned around a fire pit, offering a relaxing spot to enjoy the outdoors. A picnic table is seen nearby. The wooded area opens to a view of the Green River, which flows gently past the site, framed by lush greenery.

Flat in Williamstown

Studio In Town, By the Water, Walk to Shops/Campus

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

4.95 out of 5 average rating, 146 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

4.99 out of 5 average rating, 171 reviews

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.

Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

4.99 out of 5 average rating, 160 reviews

The exterior of a two-story house is displayed, featuring a combination of white siding and a metal roof. An American flag hangs from the porch, surrounded by greenery and flower beds. The front pathway leads to a welcoming porch space.

Flat in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town , pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Guest suite in Charlemont

A spacious living area is characterized by a combination of blue and neutral tones. A comfortable bed is positioned against one wall, while a cozy seating area contains a sofa and armchair. Natural light enters through an open door that leads to a kitchen beyond.

4.91 out of 5 average rating, 218 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

4.96 out of 5 average rating, 121 reviews

The living area features a comfortable seating arrangement with a patterned armchair and a light-colored sofa accented by a vibrant throw. A side table is positioned next to the sofa, and a wall clock adds a decorative touch, while wooden flooring enhances the cozy ambiance.

Flat in Troy

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

4.97 out of 5 average rating, 354 reviews

A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

5 out of 5 average rating, 213 reviews

A terrace area is seen, featuring a glass-topped dining table surrounded by metal chairs. A stone pathway leads to well-maintained gardens with various plants and neatly trimmed shrubs in the background. Bright sunlight illuminates the scene, conveying a serene outdoor setting.

Home in Hudson

Garden Paradise minutes from Hudson

We are just a 10 minute drive from Hudson's bustling Warren Street in the historic hamlet of Claverack. We live on the property, but our guesthouse is separate and private. It's all surrounded by our 2 1/2 acre garden, which is our passion as well as our profession. We've recently adapted a 2 year old standard poodle named Nora. She is a very shy little girl, and will win your heart. We are sorry, but we do not accept pets or children under 12.

4.93 out of 5 average rating, 144 reviews

A spacious studio apartment is highlighted by a large bed adorned with neutral bedding and vibrant throw pillows. A kitchenette with red accents is visible in the background, featuring modern appliances. A work bar with high chairs offers additional seating, while warm wood flooring complements the overall decor.

Flat in Rhinebeck

Private Studio Close to Downtown Rhinebeck

This modern studio apartment is ideal for a weekend retreat or remote working base. Just 17 minutes from Omega, we offer a Queen-size bed, free WiFi, and a Smart TV. The fully-equipped kitchenette and work/eating bar make meal prep and productivity easy. The bathroom features a rain shower head and Bluetooth speaker. With its own entrance and ample street parking, it ensures privacy and convenience. Give it a try – you won’t be disappointed!

4.9 out of 5 average rating, 429 reviews

An open living area features exposed wooden beams and concrete floors. A cozy seating area is arranged next to a patterned area rug. The adjoining bedroom area displays a spacious bed and mirrors reflecting the natural light that fills the room.

Guest suite in Hudson

Historic Hudson Hideaway

Historic Hudson Hideaway is the first floor of our 1840s home furnished with a mix of modern finds, antique textiles, and luxury linens. The suite has an abundance of natural light and is ideal for those looking for privacy and retreat while being conveniently located a block from Hudson's Amtrak station, and steps to Warren Street shops, restaurants, bars, and arts. City of Hudson Lodging Licensee #1168

Popular amenities for rentals with breakfast in Lenox

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with breakfast

4.97 out of 5 average rating, 73 reviews

A spacious living room features a large sectional sofa arranged around a central coffee table. The natural wood ceiling and light hardwood floors create a warm ambiance. A bookshelf filled with various items and plants lines one wall, while large windows provide ample natural light.

Home in Hudson

Secluded Hudson mid-century - pool & hot tub

4.97 out of 5 average rating, 143 reviews

A cozy red cabin is positioned on a snowy landscape, featuring a covered porch and large windows. Snow-covered trees frame the property, and a white expanse of the lake is visible in the background, reflecting the clear blue sky.

Home in Goshen

Lake Escape

4.89 out of 5 average rating, 1,002 reviews

A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.

Home in Feeding Hills

Farm Fresh Feeding Hills

5 out of 5 average rating, 54 reviews

A spacious kitchen features modern appliances and a large wooden island. Vintage cabinetry with glass display shelves complements the rustic atmosphere. Natural light streams in through a window above the sink, illuminating the wooden ceiling and exposed brick walls.

Home in Coxsackie

Explore the Woodland Areas at Circa 1804 Farmhouse

5 out of 5 average rating, 106 reviews

A spacious kitchen features modern appliances and elegant cabinetry. A gas stove is positioned beneath a stainless-steel hood, while a farmhouse sink is complemented by stylish fixtures. Light-colored countertops are paired with a herringbone backsplash, creating a fresh and inviting cooking space.

Home in Delmar

Rustic Farmhouse Meets Chic!

4.88 out of 5 average rating, 133 reviews

A charming pink house is framed by a snowy landscape, creating a vibrant contrast with the white snow. A stone pathway leads to the entrance, flanked by snow-covered plants. A decorative green tree structure stands in the foreground, adding to the winter scene.

Home in Kinderhook

Jenny’s Folk Art Museum

5 out of 5 average rating, 32 reviews

A bright living area features large windows offering views of the lake. A round table with pink tablecloth is surrounded by black chairs. Two comfortable purple armchairs flank a light wood coffee table, while a bedside table with a lamp adds function to the space.

Home in Goshen

Light-filled Lake House in Goshen

4.99 out of 5 average rating, 210 reviews

A bright and spacious studio features a cozy futon couch in a rich purple hue, paired with a wooden coffee table. A small dining area is set with a flower vase, while angled ceiling adds character. A kitchenette area is visible in the background.

Home in Williamsburg

Hilltown Studio

Apartment rentals with breakfast

4.83 out of 5 average rating, 240 reviews

A cozy bedroom features a king-sized bed with layered bedding and neatly arranged towels. Natural light filters through two large windows dressed in soft curtains, highlighting a vintage wooden dresser and an inviting ambiance.

Flat in Tivoli

Ground Floor Apartment on Hudson River

4.53 out of 5 average rating, 58 reviews

A comfortable living area features a tan leather sofa adorned with decorative pillows. A simple coffee table sits in front, with a remote placed on it. Two tall floor lamps provide ambient light. A plant adds a touch of greenery, and a framed artwork decorates the wall.

Flat in Mansion Area

“Private 3-Level Retreat Near Downtown Albany”

4.98 out of 5 average rating, 118 reviews

A cozy sleeping area features a spacious bed with white bedding and a decorative pillow. A low table with a bedside lamp stands beside the bed, and a small seating area with a blue and white striped chair is visible. A patterned area rug adds warmth to the floor.

Flat in Hudson

Private Hudson pied-à-terre; blocks from Amtrak

4.96 out of 5 average rating, 361 reviews

A spacious living area features a large brown sofa adorned with varied cushions. A wooden coffee table holds a magazine and a potted plant. In the background, a dining table set for four is visible, alongside a well-equipped kitchen area, creating an inviting communal space.

Flat in Rexford

Need a Getaway??

4.96 out of 5 average rating, 242 reviews

A cozy living room features an arrangement of plush sofas and an accent chair around a glass coffee table. Natural light filters through sheer curtains, illuminating the art on the walls and the decorative fireplace, which is complemented by plants and a unique mirror.

Flat in Hudson

Bright, Charming 3-BR with Garden in Heart of Town

4.72 out of 5 average rating, 65 reviews

A spacious living area features a comfortable sectional sofa and a coffee table. Bright windows allow natural light to fill the room. A dining area is visible in the background, with a large table and chairs. A wall decor piece depicting the Eiffel Tower adds a cultural touch.

Flat in Troy

Comfortable Stay 2

4.89 out of 5 average rating, 236 reviews

The bedroom features a spacious white upholstered bed with a dark bedspread and multiple pillows. A desk and chair are positioned near large windows, complemented by dark curtains. Hardwood floors are visible, adding warmth to the space.

Flat in Downtown Albany

Downtown Albany 2 Bedroom + Workstation @ The Mark

5 out of 5 average rating, 3 reviews

A cozy living area features a comfortable couch adorned with soft pillows, complemented by a wooden coffee table. An adjacent kitchen area with modern bar stools offers ample space. Natural light flows through the open layout, and a staircase leads to an upper level.

Flat in Hancock

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Bed and breakfast rentals with breakfast

Private room in North Chatham

4.97 out of 5 average rating, 577 reviews

Charming Eyebrow Colonial North Chatham, NY

Place to stay in Ashfield

The entrance of a traditional BnB features a vibrant orange facade and a prominently displayed red door. Two white columns frame the entry, while a charming balcony is visible above. Seasonal flowers in pots add a welcoming touch to the porch area, which is adorned with fallen leaves.

5 out of 5 average rating, 14 reviews

Norton Hill BnB

Private room in Bennington

A cozy bedroom features a spacious bed adorned with a floral quilt. Soft light filters through the window, casting gentle shadows on the bed. Two bedside tables with lamps flank the bed, and framed art pieces are displayed on the walls.

4.99 out of 5 average rating, 135 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

4.96 out of 5 average rating, 404 reviews

Private room in Athens

Brick Row House in the Woods, private 2nd floor

Private room in Sheffield

The rustic timber structure is surrounded by a vibrant forest, showcasing autumn foliage in shades of gold and red. Large, multi-pane windows provide a view of the inviting interior, while a welcoming porch extends from the front entrance.

4.98 out of 5 average rating, 56 reviews

Sheffield Lodge - Ramblewood Master

4.97 out of 5 average rating, 379 reviews

Private room in Troy

The Sara Tracy House, Eliot Room

Private room in Sandisfield

A cozy living room is characterized by wooden beams and warm wood paneling. Comfortable seating is arranged around a central area rug, with plants adorning the space. Natural light fills the room through large sliding glass doors that open to a deck.

4.93 out of 5 average rating, 150 reviews

Hospitality in the Berkshire Woods