Vacation rentals with breakfast in Stockbridge

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Top-rated breakfast rentals in Stockbridge

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Top guest favorite

An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.

Home in Saugerties

4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

Pristine 3 BR, 2.5 bath ranch in a quiet cul-de-sac. 3/4 mile walk to the Hudson River and a 2 minute drive to HITS, village restaurants and shopping. Features a fully stocked open plan kitchen and skylit dining room, an oak bar, spacious living room and a sunny deck overlooking the fenced in backyard with a patio and a swimming pool. Large finished walk-out basement with washer & dryer, ping-pong, arcades,exercise room 65 in SmartTV & Wifi Split Units A/C & heat Gazebo with outdoor fireplace

Superhost

A rustic wooden bench is positioned in the foreground, offering a view of a small fish pond nestled among greenery. Lush plants surround the pond, adding to the tranquil setting, which invites relaxation in a natural environment.

Cottage in Canaan

4.85 out of 5 average rating, 169 reviews

Cozy Little Cottage

Small comfortable place close to Lime Rock Park and Ski Butternut. It has 3 available bedrooms including one master with full bath. Lots of great restaurants in the area and places to hike or take out your canoe or kayak. Nice private backyard. There is a small fish pool to enjoy. I do have cameras pointing at the front door and back door to see when guests arrive and when they leave. Please don't try and sneak in extra guests you didn't intend to pay for. I've has these issues before. Welcome!

Top guest favorite

An outdoor seating area features a spacious deck with comfortable red chairs and a central fire pit. Two umbrellas provide shade, while scenic mountain views are visible beyond the vibrant red guest house.

Guesthouse in North Adams

5 out of 5 average rating, 263 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, 131 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.

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.

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, 125 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.