Holiday rentals with breakfast in Pioneer Valley

Find and book unique Holiday Accommodation with Breakfast on Airbnb

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Popular amenities for Pioneer Valley Holiday Accommodation with Breakfast

Holiday House Rentals with breakfast

Home in New Marlborough
5 out of 5 average rating, 8 reviews

All-Season Berkshires Escape: Ski, Hike, Swim

MeghanRating, 5 stars46 months ago
The house is great for a family or group, with ample bedrooms and spacious common areas to hang out. The location is serene and peaceful, and Josh and Emily were attentive and responsive hosts. Highly recommend!
Guest favourite
Home in Bennington
5 out of 5 average rating, 48 reviews

The Henry House & Authentic Red Covered Bridge

JacquelineRating, 5 stars10 months ago
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.
Top Guest favourite
Home in West Brattleboro
4.93 out of 5 average rating, 118 reviews

Modern Spacious Home with Mountain Views

AmyRating, 5 stars1 month ago
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!
Superhost
Home in Amherst
4.82 out of 5 average rating, 17 reviews

Great/Ideal place near UMass for Graduation

DianeRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Brimfield
4.93 out of 5 average rating, 167 reviews

Brimfield Lakeside Home Away from Home

JeffreyRating, 5 stars1 month ago
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.
Superhost
Home in Lenox
4.88 out of 5 average rating, 8 reviews

Whistler's Inn/The Garden Room (#9)

Mary EllenRating, 5 stars9 months ago
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!
Guest favourite
Home in Longmeadow
4.96 out of 5 average rating, 81 reviews

★Unique Suburban Retreat Cozy Comfy Pet Friendly★

Kristen AnneRating, 5 stars5 months ago
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.
Guest favourite
Home in Simsbury
5 out of 5 average rating, 12 reviews

Charming Cottage next to Flamig Farm

JoeRating, 5 stars3 days ago
Julia's place was as advertised. It was clean and well maintained. We were in the area for a family wedding. It was myself, my wife and two young adults -space was fine for four. Home was spotless with a fully appointed kitchen. We only used it for breakfast ...but you can prepare a full meal. The fresh eggs from the little farm across the street was a nice touch.

Apartment rentals with breakfast

Apartment in Shaftsbury
4.48 out of 5 average rating, 75 reviews

Bungalow Apt Farm Stay

KellyRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Dummerston
4.92 out of 5 average rating, 412 reviews

~Serene Barn Retreat~

AshaRating, 5 stars2 weeks ago
We had a wonderful stay in this peaceful airbnb. We loved the layout and the views of the forest. The king size bed was super comfortable and Brianna was accommodating of my husband's need for down-free bedding. The exposed beams from the original barn and the natural wood made the apartment warm and cozy, especially during a powerful rainstorm. Highly recommend visiting the tiny cemetery down the road!
Top Guest favourite
Apartment in Canaan
4.99 out of 5 average rating, 144 reviews

West Main

AlexisRating, 5 stars2 weeks ago
Loved this little apartment. It has everything you need and more.
Apartment in Colebrook
5 out of 5 average rating, 25 reviews

Rural retreat in Colebrook CT

CarrieRating, 5 stars28 months ago
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.
Guest favourite
Apartment in Deerfield
4.93 out of 5 average rating, 60 reviews

Nestled Inn

CatherineRating, 5 stars1 month ago
Great stay, had everything we needed. Host was very accommodating!
Guest favourite
Apartment in Stephentown
4.95 out of 5 average rating, 39 reviews

2 Bed Berkshire Getaway @ Stephentown Hotel

GianninaRating, 5 stars2 months ago
We booked a quick in and out mini trip from Long Island. It was so easy to get there, perfect location if you’re looking to get away from the hustle and bustle and need to unplug for a bit. We booked one of the larger apartments since we were traveling with 3 kids and our dog. We felt right at home, the design and decor allowed us to cozy up quickly. They put effort into the small details that provide the comfort you’re looking for when being away from home. Tons of games to play with the family, comfortable mattresses, perfect lighting, stocked kitchen. Everything you need to start a fire outside along with s’mores kits. The boys played ball and with a few other things that were provided in the outdoor bins. The kids were also very interested learning about the history of the actual hotel and location, and how the history of it has been preserved while creating something beautiful and cozy for families. The place smelled great and was spotless.
Top Guest favourite
Apartment in Brattleboro
4.99 out of 5 average rating, 141 reviews

River View apartment

ScottRating, 5 starstoday
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.
Guest favourite
Apartment in Brattleboro
4.89 out of 5 average rating, 567 reviews

Cozy, Private & Great location for exploring VT !

VincentRating, 5 stars2 weeks ago
Very lovely place located in a nice part of town. Mary and Lance were very welcoming and nice. We had a great stay and I strongly recommend this place for staying in Brattleboro.

Bed and breakfast rentals with breakfast

Top Guest favourite
Private room in Deerfield
4.99 out of 5 average rating, 184 reviews

Queen bed suite, full breakfast, five stars

Cristiany and ToddRating, 5 stars3 weeks ago
Yet another wonderful 5-star stay at Jane & Karl's lovely home in Deerfield. Delicious homemade breakfasts, spacious and clean rooms, and always a warm welcome from Jane & Karl. Have stayed over 10 times across 3 years, and every time has been great - and there's always an improvement each time!
Place to stay in Ashfield
5 out of 5 average rating, 14 reviews

Norton Hill BnB

JohnRating, 5 stars1 month ago
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!
Top Guest favourite
Private room in Bennington
5 out of 5 average rating, 121 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

MontseRating, 5 stars2 weeks ago
As usual, everything perfect at Ernie's. It's a great place to be.
Guest favourite
Private room in Suffield
4.9 out of 5 average rating, 88 reviews

The Lily House - Liv's Garden Room

DaraRating, 5 stars3 weeks ago
I love staying at Lily’s House. It is extremely convenient for my visits and it is always my first choice accommodation.
Guest favourite
Private room in Sunderland
4.94 out of 5 average rating, 198 reviews

Private 2nd Floor Studio Apartment With a View!

GayleRating, 5 stars1 month ago
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
Top Guest favourite
Private room in Amherst
4.93 out of 5 average rating, 208 reviews

BigSkyHilltop: Queen & single bed, full breakfast

PatriciaRating, 5 stars9 months ago
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.
Top Guest favourite
Private room in Brimfield
4.95 out of 5 average rating, 412 reviews

New England Escape

EmilyRating, 5 stars3 weeks ago
I was thrilled with my stay at this beautiful Airbnb, it met and exceeded all my expectations. The place was clean, quiet, private, and equipped with everything I needed to be perfectly comfortable. I would definitely stay again, and highly recommend to anyone who needs a place to stay!
Top Guest favourite
Private room in Brattleboro
4.91 out of 5 average rating, 102 reviews

The Purple Chef's House

RoiRating, 5 stars8 months ago
Beautiful house and amazing hostess! We both had a great time. Sharon is super friendly and very helpful. Can't wait to come again ❤️

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