Vacation rentals with breakfast in Stockbridge

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Top-rated breakfast rentals in Stockbridge

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Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Oct 7 – 14

G$26,055 GYD per night

Guest favorite

Yurt in Pattersonville

4.99 out of 5 average rating, 778 reviews

Mariaville Goat Farm Yurt

A peaceful, charming, 20’ yurt in the woods on our small, off-the-grid goat farm! If you are looking to get away from it all (and still be close to SO much) - this is the place for you! Enjoy a nap in the hammock, s’mores around a campfire, a great night’s sleep under the stars, a country breakfast delivered to your door - and goats! Take a walk in the woods...enjoy the unique landscaping...try goat yoga! Or, experience some of the area’s AMAZING food, beverages, shopping, and attractions!

Oct 29 – Nov 5

G$30,693 GYD per night

Guest favorite

Apartment in Williamstown

4.96 out of 5 average rating, 299 reviews

New Studio In Town, By the Water

★ 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.

Mar 26 – Apr 2

G$34,297 GYD per night

Guest favorite

Apartment in Canaan

4.98 out of 5 average rating, 104 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.

Jul 8 – 15

G$27,439 GYD per night

Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 158 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.

Nov 27 – Dec 4

G$25,769 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Nov 13 – 20

G$29,327 GYD per night

Guest favorite

Guest suite in Charlemont

4.9 out of 5 average rating, 182 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

Dec 16 – 23

G$22,373 GYD per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 647 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Dec 19 – 26

G$22,299 GYD per night

Guest favorite

Guest suite in Easthampton

4.97 out of 5 average rating, 401 reviews

Goreytastic Private ApARTment @ the EMC

Self-contained completely private in-law Edward Gorey inspired artistic apartment at the Easthampton Music Conservatory (right off the Williston Campus.) Romantic, campy, silly, spooky, quirky space with Edward Gorey and original artwork, a micro library including classic TV shows and popular B movies, vintage Nintendo system & oversized beanbags for Nintendo aficionados of all ages. To be clear: entirely self-contained space. Private EVERYTHING. NO shared spaces.

Sep 11 – 18

G$20,285 GYD per night

Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 264 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.

Feb 2 – 9

G$35,841 GYD per night

Guest favorite

Condo in Hudson

4.94 out of 5 average rating, 141 reviews

Harmony Valley Home, bright & inviting 2-BR escape

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries breweries Musuems Hiking trails Empire State Rail Trail Conservation Areas

Oct 29 – Nov 5

G$28,754 GYD per night

Guest favorite

Apartment in Dummerston

4.93 out of 5 average rating, 366 reviews

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Aug 14 – 21

G$26,829 GYD per night