Vacation rentals in Pioneer Valley

5 out of 5 average rating, 10 reviews

Home in Wilmington

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

VanessaRating, 5 stars1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

4.86 out of 5 average rating, 125 reviews

Home in Readsboro

Beautiful Vermont! (Pet Friendly)

JudahRating, 5 stars4 months ago

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

4.91 out of 5 average rating, 98 reviews

Two blue Adirondack chairs are positioned on a wooden deck overlooking a lush green lawn and Sadawga Lake. A gas grill is situated nearby. Soft shadows are cast on the deck from the chairs, with the sky above featuring scattered clouds and sunlight.

Tiny home in Whitingham

Cozy Lakeside Tiny Home, Near Skiing

MelissaRating, 5 stars1 month ago

We had a lovely time at this tiny home. It was quiet and relaxing which is exactly what we were looking for. We enjoyed the hot tub and the sunny living room. It was cozy and cute. We took a few trips to Wilmington for food. It’s a cute town. We’d like to come back when the weather is better to enjoy some kayaking and hiking in the area.

4.91 out of 5 average rating, 117 reviews

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

FeliciaRating, 5 stars2 months ago

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

4.99 out of 5 average rating, 109 reviews

A patio area is set with a round table and four chairs under a large umbrella, offering views of the river. A grill is positioned nearby, and flower planters enhance the space. Lush greenery is visible across the water, framed by a clear blue sky.

Home in Canton

Best River View, on Rail Trail in Collinsville!

AmyRating, 5 stars3 weeks ago

I reached out to Carol after we had been in a horrible Air B&B situation in a near by town.. She accommodated us on the very day we needed to check in. Her place is stunning! And very charming. The views are to die for. We had everything we needed. I would definitely stay there again and would highly recommend her place. Also, snacks and essentials were left for us and plenty of coffee! I will never forget the beautiful view sitting in the family room overlooking lake.

4.94 out of 5 average rating, 163 reviews

Home in Brimfield

Brimfield Lakeside Home Away from Home

MaureenRating, 5 stars1 week ago

My sister and I spent a few relaxing days at Shannon's home. We had a wonderful time! It's in a great location- close enough to town to see the sights and go to restaurants, but also far enough away to be so peaceful and private. We booked it because we love being near water, and the house didn't disappoint. We loved the view. It was a bit windy and cool while we were there, but we were able to sit outside several times by the lake and use the fire pit. We also enjoyed watching and listening to the many birds around the house. The house itself was warm and comfortable and had everything we needed. We were happy to meet Shannon when we checked in. She answered questions we had and made recommendations based on our conversation. Thanks Shannon for having us, and we would love to come back sometime to your lovely home! Highly recommend!!

5 out of 5 average rating, 6 reviews

A bright dining area features a round white table with metal chairs, positioned near large glass doors that open to a snowy outdoor view. Natural light fills the space, complemented by light-colored walls and a modern pendant light overhead.

Home in Great Barrington

Summer & Leaf Season Rental!

AnnieRating, 5 stars3 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Pioneer Valley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pioneer Valley

Apartment in Great Barrington

A serene lake is framed by lush greenery and autumn foliage, with vibrant reds and yellows reflecting on the water's surface. The sky is dotted with soft clouds, complementing the tranquil atmosphere of the natural setting.

4.78 out of 5 average rating, 18 reviews

Writer's retreat: study, books, fireplace (Ecobnb)

MelaRating, 5 stars5 months ago

The location and space were great! I worked remotely during most of my stay and was very comfortable with my set up. The dining table was a perfect desk, with good lighting and wifi! Slept well due to it being so quiet at night. A positive experience overall.

5 out of 5 average rating, 7 reviews

A wooden deck is visible, offering seating with blue rocking chairs. Lush greenery and a serene lake are seen in the background under a partially cloudy sky. The space invites relaxation and enjoyment of the natural surroundings.

Home in Granby

Lake house retreat Granby CT

DianeRating, 5 stars1 week ago

We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

4.93 out of 5 average rating, 14 reviews

Home in Monroe

The Camp

BrendaRating, 5 stars2 months ago

We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!

4.81 out of 5 average rating, 80 reviews

Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

BethanyRating, 5 stars2 months ago

We enjoyed our stay at Elijah’s place. It was just as described and Elijah was very responsive before and during our stay.

5 out of 5 average rating, 16 reviews

A spacious front porch is shown, featuring two comfortable rocking chairs with cushions. Surrounding greenery provides a lush backdrop, and a round woven rug is located beneath the chairs. Natural light illuminates the area, enhancing a tranquil outdoor setting.

Home in Lanesborough

Berkshire Mountain House

DestinyRating, 5 stars1 week ago

This Airbnb exceeded our expectations! The house is spacious and super family friendly (also great for just adults). We loved the Airbnb so much that we only left the house once. Our hosts were very attentive and accommodating. I would recommend to anyone who is looking for a getaway in the Berkshires no matter the season.

4.92 out of 5 average rating, 153 reviews

A spacious bedroom features a green wooden bed dressed in white linen, flanked by large windows with sliding doors leading to a serene outdoor view. A comfortable armchair and a small side table are positioned nearby, adding to the cozy ambiance.

Home in Otis

The Pinnacle House at Otis Ridge Ski Area!

AmyRating, 5 stars2 months ago

Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.

4.79 out of 5 average rating, 123 reviews

A serene stream flows gently past smooth stones and moss-covered rocks, with the foliage of trees surrounding the scene. In the background, a building with multiple balconies is partially visible, reflecting the natural beauty of the area.

Villa in South Lee

Villa with Access to Amazing Amenities!

PamelaRating, 5 stars6 months ago

The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.