Vacation rentals with breakfast in Stockbridge

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Top-rated breakfast rentals in Stockbridge

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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, 130 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 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, 137 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 green wooden arbor frames a lush garden scene, featuring large hosta plants with delicate flowers. A blue bench invites relaxation among the greenery, while trees provide a natural canopy overhead, creating a tranquil outdoor space.

Home in Williamsburg

4.99 out of 5 average rating, 183 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 spacious interior is displayed, featuring a living area with comfortable seating and two beds. Large windows allow natural light to fill the space, enhancing the inviting atmosphere. Decor elements include artwork and cozy textiles, creating a homely environment suitable for relaxation.

Guest suite in Charlemont

4.91 out of 5 average rating, 206 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

Guest favorite

A rustic wooden door features hand-painted text reading 'KEEP OUT' and 'THE THREE FLIRS.' The door is attached to a quaint wall, with a black-framed mirror visible to the left and a glimpse of a warm-toned living area in the background.

Guest suite in Hudson

4.98 out of 5 average rating, 105 reviews

Private Hudson pied-à-terre; blocks from Amtrak

Private hideaway on Warren Street--entire floor--in a renovated, historic 18th Century house. Queen bed, en suite bathroom, cozy living area with fridge and coffee maker plus a large private deck with panoramic city and mountain views. Walk to everything, from Basilica to Rivertown. Includes light breakfast with locally baked breads and coffee/tea delivered to your door. (Rate now reflects 4% Hudson lodging tax.) Note: Masks still required in hallways and shop. Thank you.

Guest favorite

A spacious sunroom features multiple large windows allowing natural light to fill the area. Wooden flooring complements the simple decor, which includes a rocking chair and a variety of potted plants. A rustic table and circular rugs add to the serene ambiance of the space.

Guest suite in Stanfordville

4.93 out of 5 average rating, 151 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.

Top guest favorite

A tranquil pond area surrounded by lush greenery and trees. Water lilies float on the surface, adding color to the serene setting. The pond is framed by a stone border, creating a natural and peaceful environment, perfect for quiet contemplation.

Home in Salisbury

4.98 out of 5 average rating, 128 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 vibrant assortment of flowers, featuring rich red and white blossoms among lush green foliage, creates a lively garden display. The plants are adorned with a striking maroon and green variety, adding texture and color to the scene.

Apartment in Troy

4.96 out of 5 average rating, 114 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 white trellis adorned with climbing roses in shades of red and purple creates a charming focal point in the garden. Neatly trimmed round hedges frame the scene, complemented by clusters of white roses, enhancing the lush greenery of the surrounding garden space.

Home in Hudson

4.99 out of 5 average rating, 198 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.

Top guest favorite

Two wooden Adirondack chairs face a small fire pit, surrounded by a serene wooded area. A picnic table is positioned nearby, with a stack of firewood to the side. The Green River flows gently in the background, framed by vibrant greenery.

Apartment in Williamstown

5 out of 5 average rating, 124 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

Guest favorite

An outdoor fire pit area features four red lounge chairs arranged around a circular gravel space. Soft lighting from nearby fixtures enhances the peaceful surroundings, while tall trees provide a natural backdrop, creating a secluded atmosphere for relaxation.

Home in Ghent

4.95 out of 5 average rating, 242 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!

Superhost

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.