Vacation rentals with breakfast in Stockbridge

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Top-rated breakfast rentals in Stockbridge

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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, 272 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.

Guest favorite

An open-plan kitchen features a wooden countertop and a gas cooktop. A three-sided fireplace creates a focal point in the living area, which includes dining space with a wooden table and chairs. Exposed beams add character to the room, warmly illuminated by natural light.

Home in Stockbridge

4.94 out of 5 average rating, 136 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

A serene brook flows through the image, revealing clear water that reflects the surrounding greenery. Smooth stones line the water's edge, and overhanging leaves create dappled light patterns on the surface. The peaceful landscape suggests an inviting area for relaxation.

Apartment in Charlemont

4.99 out of 5 average rating, 158 reviews

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 !

Top guest favorite

A winter scene is depicted with a red building contrasting against a vibrant sunset sky, filled with shades of orange and pink. Snow covers the ground and rooftops. Dark trees frame the image, contributing to the serene atmosphere.

Apartment in Canaan

4.99 out of 5 average rating, 144 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 deer is seen partially hidden among lush, green foliage, with long, slender plant shoots reaching upwards. The background features a rustic wooden structure with a darkened entrance, contrasting with the vibrant greenery in the foreground.

Home in Williamsburg

4.99 out of 5 average rating, 190 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Guest favorite

A ceramic figure of a golden cocker spaniel is positioned on a tiled floor. The statue showcases detailed fur texture and expressive eyes, contributing a charming element to the entry area. Its warm tones complement the surrounding space.

Guest suite in Charlemont

4.91 out of 5 average rating, 210 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

Top guest favorite

A spacious wooden deck is surrounded by greenery, featuring a white lounge chair positioned for relaxation. A small table and decorative plant pots with flowers are visible, enhancing the natural setting. Sunlight filters through the trees, creating a serene outdoor space.

Home in Salisbury

4.98 out of 5 average rating, 129 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

A homemade baked dish is presented on a decorative glass plate, showcasing a caramelized fruit topping. Nearby, a colorful mug filled with a warm beverage complements a ceramic pitcher. The setting is arranged on a light-colored countertop, creating a cozy atmosphere for enjoying snacks.

Apartment in Troy

4.96 out of 5 average rating, 116 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 wooden sauna is showcased with glass doors, highlighting a spacious interior with wooden benches and a soothing blue light. Natural light filters in through a window, adding warmth to the inviting atmosphere.

Farm stay in Ancram

4.96 out of 5 average rating, 335 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 standard poodle with a curly black coat is positioned against a snowy backdrop. The dog wears a blue harness and has light snowflakes clinging to its fur. Soft sunlight creates a gentle reflection on the white ground.

Home in Hudson

5 out of 5 average rating, 201 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.

Guest favorite

The exterior of a historic two-story home is shown, featuring a deep blue facade and white trim around the windows. A small front porch with steps leads to the entrance, surrounded by greenery and colorful foliage, set against a clear blue sky.

Guest suite in Hudson

4.9 out of 5 average rating, 419 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

Guest favorite

A small table with a dark metal frame is positioned next to a koi pond surrounded by greenery. Two armchairs, each adorned with light-colored, textured covers, are placed nearby, offering a peaceful spot to enjoy nature. Sunlight filters through the trees, creating a serene setting.

Guesthouse in Ulster Park

4.85 out of 5 average rating, 483 reviews

Hudson Valley Hideaway

Nestled in the Hudson River Valley an intimate apartment ideal for one or two. 85 miles from NYC, Conveniently located 20 minutes to New Paltz, Mohonk, Woodstock and Bard College. Enjoy a stroll on the land with your morning tea or coffee and visit the koi pond. Check out this wonderful review from the marvelous friends at &north! http://andnorth.com/stay/artist-owned-airbnb-cottage-tucked-away-esopus-ny/