Holiday rentals with breakfast in Pioneer Valley

We had an excellent stay at Henry House. The interior was cozy and well decorated - with so many extra touches. Our favorite activity was sitting on the lovely front porch, looking out at the spectacular landscaping and watching the world pass by on the quiet country road. We highly recommend this rental for a large party.

Beautiful surroundings to this sweet little house in the mountains. Very comfortable. Lots of towels and linens. Snacks and local restaurant guide. Stores about 15 minutes away. Center of Bennington shops about 10 minute drive. Lots of games provided if you want. The yard is huge and has outdoor seating. The beds and pillows were soft. Plenty of seating in living room and kitchen. Overall a good stay!

Christine went above and beyond in welcoming us to her place. The fridge was stocked and she gifted us with homemade treats at the beginning and in the middle of our stay. Her place is spacious, clean, and comfortable. We enjoyed adventuring on the walking paths behind the house and her guestbook offered wonderful tips for Brattleboro and the surrounding area. We had a wonderful time!

We enjoyed our stay — perfect location for visiting UMass! Raphael was a terrific host, friendly and helpful. Beds were super comfortable, pretty linens, and the kitchen had everything we needed. We hope to stay again next time we visit Amherst.

We had a fantastic stay at Shannon’s lake house! From the start, Shannon’s communication was excellent, making check-in and getting settled a breeze. The house itself is full of charm and offers a stunning view of the lake. It was impeccably clean, and the beds were very comfortable — a perfect retreat for our family. We were visiting my son's school and chose this property because of its convenient location and the opportunity for him to fish — one of his favorite activities. Shannon went above and beyond by charging the boat battery, ensuring everything was ready when the weather improved. Thanks to her, my son was able to catch several fish, including his first trout and smallmouth bass — a memory he won’t forget! Shannon lives next door and strikes the perfect balance between being available if needed while giving you complete privacy to enjoy the property. We would absolutely recommend this place to others and look forward to booking again in the future.

Gorgeous place in a great, walkable location. Our room was very clean & comfortable. Breakfast was excellent. Our host filled us in on the history of the inn and what's going on in Lenox. Hope to stay again soon!

I really liked staying in this Airbnb and it’s prime location in Longmeadow, Massachusetts. It was convenient to my parents home, who I was visiting. There was a polar vortex and the home was so toasty warm and cozy! I really enjoyed getting back there at the end of my day. This AirBnB is one of the better stocked properties I’ve stayed at. They had plenty of towels, sheets, extra fleece blankets, and kitchen items. Many times when I stay at a place I will run out of things such as garbage bags and paper towels, and there aren’t any extra there. That wasn’t the case at Robert’s property. He was very, very thoughtful in setting up this home for guests! I’ll be back! Thank you.

We loved the location and scenery! The petting zoo was great entertainment for the children in our down time. The cottage was adorable and so welcoming. Julia was a fabulous host and super responsive. We enjoyed our time there and plan to return if the opportunity presents itself in the future.

if you want to channel something between Paris, Saratoga, and New Orleans in VT. This is the place. Warm. Friendly. Full of Amy's artistic touch. Everything you need is provided. Bring your essentials and food. Lovely stay. Will be back.

Loved this little apartment. It has everything you need and more.

Spent the Memorial Day weekend in Great Barrington as part of a cycling club from NYC. My primary concern was having a safe place to store my bike (expensive road bike). Host was very accommodating, allowing me to store inside home.

Marge was an amazing host who went to effort to ensure we were comfortable and taken care of. For example, in advance of our arrival she asked what type of bread and juice we preferred and if we wanted milk or cream for our coffee. She providd fresh eggs and even sent a dozen to our daughter who lives down the street. The apartment was welcoming, clean and cozy. The kitchen and pantry were well-supplied to meet our needs. We will definitely stay at Marge's next time we visit our daughter.

Great stay, had everything we needed. Host was very accommodating!

Susan's place is exactly as advertised and more. Very comfortable and well-equipped space with nice extras - coffee, tea, snacks, firewood and a grill with grill spatula, etc. Quiet, country setting that is a great value compared to hotels in the area. Would recommend and stay again.

It’s hard to imagine a more perfect stay in Northampton. Bright, tasteful, calming, well thought out and squeaky clean! Not to mention easy parking, easy walking to Smith College and downtown but just off the main drag so it’s still quiet and peaceful. Jacqueline has gone the extra mile with great coffee, various milks, welcome snacks, good toiletries, very comfy bed, etc. I loved it so much that I stayed in more than I’d planned. It’s just a pleasurable and safe feeling space to occupy. I’ll definitely be back.

Thank you Bill and Pamela! We had a great time, you made us feel right at ease in your lovely home. Great conversations, like connecting with an old friend. We'll call again next time we're in your area! -Melissa and Robert

Karl and Jane are really nice and friendly host! They provided delicious breakfast for us and gave us clear instructions for our stay at their house. The room is clean and cozy to stay. We will definitely choose to stay next time! Sally

I am so honored to have been one of the last guests who had the privilege of staying in this beautiful home. Thank you, Chris and Fran, for the wonderful conversation, the magic tricks, delicious local breakfasts, recommendations, and opening your charming historic home to our travels!

We had a graduation in Northampton and needed to accommodate many family members. Yohah’s lovely house was the perfect solution. It was homey and nicely decorated with lovely art. It was just a half hour away from Northampton, which was very convenient for us. Yohah was a great host, who was up the challenge of supporting our shifting schedule and plans. Flexible, thoughtful and an excellent cook! He also has a beautiful yard and croquet set! Truly, we could not have asked for a better experience!

We had a lovely and very comfortable stay at Michele’s place. They made the trip a wonderful and memorable weekend.

We were all staying at High Grass Farm so we could attend the Brimfield flea market and the location of this place was perfect! The house itself was very nice and cozy. When we arrived, there were fruits, granola bars, and even a cake made for us to enjoy. The host, Karen, was quick to respond to our messages and even helped us out with our dog while we were out. Overall, an amazing stay and we hope to be back again!

We had a great time staying at the Lacey Rose! I appreciated the direction communication from Denise and being in a space that was so thoughtfully decorated and cared for. Breakfast made for us at the time we requested was a huge bonus as well!

Felt like we were nestled in the range of Mount Toby. The property and studio were super quiet, super non scented and clean with plentiful views to awe at. We needed ths peaceful trip while watching our son graduate. We are huge fans of Pioneer Valley. We know this area well so we took advantage of all great foodie places and all nature locations we could pack in. We would love to visit your place again! A slice of heaven for us

I spent a wonderful 24 hours in Josette’s home. It was one of the best Airbnbs I ever stayed in. Beautiful surroundings, an amazing breakfast and a super comfortable bed. I hope to be back.