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Vacation rentals with breakfast in Stockbridge

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Top-rated breakfast rentals in Stockbridge

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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.

Apartment in Athens

4.93 out of 5 average rating, 217 reviews

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.

Top guest favorite

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.

Guesthouse in North Adams

5 out of 5 average rating, 288 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.

Top guest favorite

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

4.94 out of 5 average rating, 140 reviews

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.

Top guest favorite

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.

Apartment in Canaan

4.99 out of 5 average rating, 155 reviews

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 brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Top guest favorite

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.

Guest suite in Charlemont

4.91 out of 5 average rating, 215 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

The sunroom features multiple windows allowing natural light to fill the space. Two rocking chairs are positioned beside potted plants. A ceiling fan hangs overhead, and the wooden floor enhances the comfortable atmosphere. Views of the garden and trees are visible through the windows.

Guest suite in Stanfordville

4.93 out of 5 average rating, 160 reviews

Charming Guest Suite in the Hudson Valley

Nestled in the heart of the Hudson Valley on a quiet country road, this house features a private, newly renovated space at the back of a unique house built in 1789. Surrounded by trees and nature, it makes for a perfect relaxed setting, with access to your own private deck and back yard. A short walk to enjoy Hunns Lake and close to the Buttercup Sanctuary, Stissing Mountain trails, Pine Plains and Millbrook villages. It’s the ideal retreat for a peaceful country getaway.

A spacious living room features large windows allowing natural light to filter in. Comfortable sofas are arranged around a focal point gas fireplace, with a television nearby. A decorative rug enhances the warm ambiance, and double doors open to a wraparound deck.

Home in Lakeville

4.98 out of 5 average rating, 133 reviews

Upland Meadow Retreat - 3 bedrooms/2 baths

Very comfortable 2000 square foot ranch home - 3 bedrooms, 2 bathrooms on 2 acres is the perfect getaway for a quiet relaxing time in the country. Our house is a few minutes from Hotchkiss, Salisbury and Indian Mountain Schools - and is close to town. This is quintessential New England at its best. Enjoy a perfect country setting offering peace and quiet in a beautiful, natural environment. Easy drive from New York/Boston, close to Metro North Wassaic train station.

Top guest favorite

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.

Apartment in Troy

4.96 out of 5 average rating, 119 reviews

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!

Top guest favorite

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

4.97 out of 5 average rating, 351 reviews

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!

Top guest favorite

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.

5 out of 5 average rating, 207 reviews

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.

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

4.9 out of 5 average rating, 424 reviews

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

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

4.95 out of 5 average rating, 256 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

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Popular amenities for Stockbridge breakfast rentals

Free parking on premises

Air conditioning

House rentals with breakfast

Top guest favorite

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.

4.96 out of 5 average rating, 142 reviews

Lake Escape

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

4.89 out of 5 average rating, 995 reviews

Farm Fresh Feeding Hills

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

5 out of 5 average rating, 54 reviews

Explore the Woodland Areas at Circa 1804 Farmhouse

The living area showcases large windows with original trim, allowing ample natural light. A cozy orange couch is paired with a small black coffee table, complemented by two blue armchairs. Natural wood flooring and a geometric rug add warmth and texture to the space.

Home in Kingston

4.91 out of 5 average rating, 102 reviews

Peaceful Retreat in the Heart of Kingston

A dining area is set on a gravel patio, featuring a wooden table surrounded by six folding chairs. A green umbrella provides shade over the table, which is positioned in a grassy space, bordered by trees in the background.

Home in Kingston

4.91 out of 5 average rating, 117 reviews

Country House in the Hudson Valley near Woodstock

Top guest favorite

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.

5 out of 5 average rating, 103 reviews

Rustic Farmhouse Meets Chic!

Top guest favorite

A serene sunset view is captured over rolling hills. Three individuals relax on a grassy area while facing the vibrant sky, which transitions from orange to soft blue. In the background, fields are visible alongside parked cars, contributing to the tranquil countryside setting.

5 out of 5 average rating, 43 reviews

Little Joe Cottage in Hudson

Home in Kinderhook

4.88 out of 5 average rating, 130 reviews

Jenny’s Folk Art Museum

Apartment rentals with breakfast

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.

Apartment in Tivoli

4.84 out of 5 average rating, 234 reviews

Ground Floor Apartment on Hudson River

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, 167 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Top guest favorite

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.

Apartment in Hudson

4.98 out of 5 average rating, 112 reviews

Private Hudson pied-à-terre; blocks from Amtrak

A functional kitchen showcases modern cabinetry with open shelving displaying colorful dishware and glassware. A central island made of wood offers additional workspace. Natural light enters through a window above the sink, enhancing the bright atmosphere. Essential appliances are neatly arranged, contributing to a clean design.

Apartment in Kingston

4.83 out of 5 average rating, 121 reviews

2 bedroom / Office - HEPA Air Purifier

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.

Apartment in Rexford

4.96 out of 5 average rating, 361 reviews

Need a Getaway??

Top guest favorite

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.

Apartment in Hudson

4.96 out of 5 average rating, 239 reviews

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

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.

Apartment in Downtown Albany

4.89 out of 5 average rating, 234 reviews

Downtown Albany 2 Bedroom + Workstation @ The Mark

A spacious bedroom is highlighted by high ceilings and abundant natural light from two large windows. A king-size bed with premium bedding is centered in the room, flanked by modern nightstands. Antique wooden doors and a decorative plant add character to the welcoming space.

Apartment in Hudson

4.99 out of 5 average rating, 74 reviews

Spacious, new renovated 1BR in a Victorian mansion

Bed and breakfast rentals with breakfast

Top guest favorite

Private room in Haines Falls

5 out of 5 average rating, 76 reviews

Romantic Room near Hunter Mountain

Top guest favorite

Private room in North Chatham

4.97 out of 5 average rating, 562 reviews

Charming Eyebrow Colonial North Chatham, NY

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.

Place to stay in Ashfield

5 out of 5 average rating, 14 reviews

Norton Hill BnB

Top guest favorite

Private room in Athens

4.96 out of 5 average rating, 398 reviews

Brick Row House in the Woods, private 2nd floor

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.

Private room in Sheffield

4.98 out of 5 average rating, 51 reviews

Sheffield Lodge - Ramblewood Master

Private room in Troy

4.97 out of 5 average rating, 370 reviews

The Sara Tracy House, Eliot Room

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.

Private room in Sandisfield

4.93 out of 5 average rating, 147 reviews

Hospitality in the Berkshire Woods

Top guest favorite

Private room in Albany

4.94 out of 5 average rating, 424 reviews

Serenity in an Albany suburb

Quick stats about vacation rentals with breakfast included in Stockbridge

Total rentals
20 properties
Nightly prices starting at
G$31,362 GYD before taxes and fees
Total number of reviews
310 reviews
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore