Cottage holiday rentals in Pioneer Valley

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Pioneer Valley cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Great Barrington
4.94 out of 5 average rating, 296 reviews

Artist Cottage

LukeRating, 5 stars2 days ago
What a lovely little nook amid such beautiful hiking destinations! Everything was perfect and I would recommend to anyone looking for a relaxing getaway!
Top Guest favourite
Cottage in Pownal
4.98 out of 5 average rating, 42 reviews

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

AlbertRating, 5 stars2 days ago
An incredibly beautiful, immaculate cottage with lovely mountain views and the most thoughtful, generous, and responsive hosts! Scott and Annika absolutely deserve their title as "Superhosts." We felt like we had our own private resort with a luxurious hot tub and a fire pit under the stars. Scott and Annika sent clear instructions for how to let ourselves into the cottage and had a great online guidebook. A kind handwritten note was there to welcome us. Scott and Annika checked in with us often to ask if we needed anything, and they were quick to respond to any questions we had. They set up the cottage with extra comforts such as slippers and snacks, and we really enjoyed using the espresso machine. We were especially happy that we were able to bring our 30-lb. dog with us, and we loved exploring all of the nature and art in the nearby Berkshires and southern Vermont. We highly recommend this cottage, and we hope to go back to stay there again soon.
Top Guest favourite
Cottage in Lanesborough
5 out of 5 average rating, 20 reviews

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

CherylRating, 5 stars3 weeks ago
One of the most clean air bnb I have stayed in. It was spotless and comfortable. The hot tub and kayaks were easy to use and just a few yards walk to the water. I would not change anything about this house. And thank you Darcy for being such a great host!
Cottage in Monterey
4.68 out of 5 average rating, 19 reviews

mountain refuge

JoshuaRating, 5 stars4 months ago
My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!
Superhost
Cottage in Norfolk
4.94 out of 5 average rating, 16 reviews

The Cottage at Blackberry River Inn

RohitRating, 5 stars4 months ago
The Cottage at Blackberry River Inn was beautiful and exactly what we needed for the weekend. Breakfast was included and wonderful. This place is a gem and we will be back for sure.
Cottage in Williamsburg
4.72 out of 5 average rating, 122 reviews

Northampton-area Hot tub Pet Friendly

GeenaRating, 5 stars5 days ago
I stayed at Kate’s home for a few days with my boyfriend and my dog. We had a great time to say the least! I loved the location of the house. It’s on a long road that had a dead end with a loop, that my dog highly enjoyed walking every day! The area was peaceful. Sitting on the balcony in the morning was a great start to each day. The pool was clean. The restaurants in the area were delicious! I highly recommend “The Toasted Owl” and “D’Angelo’s”! I would stay here again!
Superhost
Cottage in Becket
4.65 out of 5 average rating, 164 reviews

A Magical Spot on Little Robin Lake

SebastianRating, 5 stars8 months ago
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.
Top Guest favourite
Cottage in Otis
4.98 out of 5 average rating, 55 reviews

Berkshire lakefront cabin with modern luxuries

AileenRating, 5 stars1 week ago
We had a wonderful time! The house is beautiful in a spectacular spot on the lake. We were four adults and a large dog and had enough space. We got to use the kayaks/paddle board and fished endless hours from the dock The kitchen is well equipped and we cooked all our meals at the house I highly recommend this place and would come back if the opportunity arises

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Lee
4.99 out of 5 average rating, 103 reviews

Charming Home in Lee

AmyRating, 5 stars4 months ago
I think this was our fifth stay at Laurie's place, which shows how much we like it. It's perfect when we visit with family, because there is plenty of space for everyone. We didn't really take advantage of it this time, but having the full kitchen is nice. We're usually there in the winter, but one day I hope to be able to enjoy the porch and the deck.
Guest favourite
Cottage in Williamstown
4.89 out of 5 average rating, 189 reviews

Cute Cozy Comfy Cottage in the Berkshires

MarleneRating, 5 stars3 days ago
We had a wonderful peaceful stay at Regina’s cottage. Everything was as described. We had our Labrador Retriever with us and the fenced yard was perfect. There are places that say dogs are allowed and then there’s a special place where they are welcomed. We are from the Berkshires and were out of our home due to construction. This is a beautiful area. For us it was peace and quiet vs. attractions. Loved the fireplace. Very comfortable bed with great linens. Regina sent check in info and it couldn’t have been any easier. GPS brought us right to the cottage which is set back from the street. You’ll be nestle between two mountain ranges. The area is beautiful. Thank you Regina!
Guest favourite
Cottage in Canaan
4.91 out of 5 average rating, 23 reviews

Historical Falls Village Schoolhouse

HalRating, 5 stars3 weeks ago
Charming home, and Cath was especially helpful with late night dining accommodations.
Guest favourite
Cottage in Warwick
4.95 out of 5 average rating, 39 reviews

By Still Waters Cottage

MeaghanRating, 5 stars1 day ago
This was our second time staying at the cottage, and once again it was a delightful experience from beginning to end. The setting is peaceful and quiet, the space was clean, and the atmosphere truly relaxing. The hosts were thoughtful and informative, making everything seamless. Without hesitation—10 out of 10 stars again!
Superhost
Cottage in Williamsburg
4.75 out of 5 average rating, 73 reviews

A Place for Peace - perfectly imperfect!

JenRating, 5 stars8 months ago
Comfortable with beautiful surroundings. Very responsive host.
Top Guest favourite
Cottage in Brimfield
4.99 out of 5 average rating, 71 reviews

Cheerful 2 bedroom cottage with lake access.

EricaRating, 5 stars2 days ago
Great place to stay if you’re in the area. We were there for a wedding so it was perfect location for us. Very private. Within walking distance to a nice lake and other walking trails. Loved having morning coffee in the sun room or patio in the mornings. Recommend and would stay there again. Gwen was very helpful and provided many local recommendations. Great little winery down the street. Was bummed we weren’t there for the antique show. Maybe next time.
Top Guest favourite
Cottage in Monterey
4.96 out of 5 average rating, 25 reviews

New! Fully renovated private cottage

FrancesRating, 5 stars2 weeks ago
Nicely appointed and updated cottage for a quiet weekend get-away. The hosts think of everything, in terms of supplies, kitchen set-up, and nice decor. I couldn’t find a kitchen item and it was delivered quickly, which was very thoughtful. Bed was super comfy and the a/c window units came in handy! A little bit of road noise during the day, but it’s not bothersome. Wish I’d been there in a season to enjoy the local town beach, which looked nice. Definitely recommend!
Guest favourite
Cottage in Canaan
4.85 out of 5 average rating, 174 reviews

Cozy Little Cottage

JessicaRating, 5 stars1 week ago
Super comfy, and adorable stay! The beds were wicked comfortable and the VHS tapes brought a great deal of comforting nostalgia! Serene backyard- with goldfish we could feed, a resident rabbit chilling near the garden, and even a few frogs! Delicious biscotti made morning coffee even more enjoyable, and the kitchen had everything to make cooking dinner easy and enjoyable! As someone with Kitchen experience, I was very pleasantly surprised that the knives here were actually sharp!! Take that onions! I also loved that some of the doors were hand painted to have a creative flare that really made this place feels special! My favorite were the bubbles on the door in the Master Bathroom! Gabriele was also really kind and fast to respond, and I was just really happy with my stay. I could honestly keep going with praise for this place but I'm running out of characters! Definitely give this place a shot and check out Umpachene Falls, only 20mins away!

Private cottage rentals

Guest favourite
Cottage in Holland
4.91 out of 5 average rating, 44 reviews

The Maybrook: Lake & Sauna

DonnaRating, 5 stars2 weeks ago
This place was everything it was said to be. it was clean and very cozy. Kyle had a booklet with useful information about the cottage, restaurants and local attractions.
Guest favourite
Cottage in Orange
4.99 out of 5 average rating, 79 reviews

Lake House with view of mountain

SoniaRating, 5 stars3 days ago
Beautiful location, comfortable rustic home with everything you need to cook and grill. Lots of stuff to do on the lake. Very serene. Charlene is super friendly and helpful. It was a really nice touch she provided a bottle of wine, juice, eggs, bagels and butter upon check in.
Top Guest favourite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars8 months ago
My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.
Superhost
Cottage in Otis
4.89 out of 5 average rating, 9 reviews

Cozy Cottage in the Berkshires

KurtRating, 5 stars9 months ago
The small home is located at the end of a 0.25 mile dirt road. There are only four homes on the road, though one is on the opposite side at the end of the road. If you are staying here you should be comfortable in an isolated location. There are no window treatments on the two sliding doors opening to the deck in the back of the home, though there is also nothing but woods in the back of the home. All that being said, the place was exceptionally clean for any Airbnb rental, much less one tucked back in the woods. While the small kitchen was missing a few expected items like steak knives, tea bags, and measuring cups, it should prove to be functional for most guests. There is a large TV in the large living room and the internet was fine for streaming without any issues. The bed was comfortable and a large dresser is available for storing clothes. Be aware that the only available heat is from a gas fireplace, two portable space heaters, and another space heater in the bathroom.
Top Guest favourite
Cottage in Holland
5 out of 5 average rating, 44 reviews

Blissfully Peaceful Cottage nestled on a lake

StephanieRating, 5 stars9 months ago
What an amazing stay! The place had great games and the porch was such a treat. The view from the fire pit was so relaxing and we enjoyed toasting smores while overlooking the lake. We ended up taking the folding chairs and playing catch by the lake, which was only a short walk away. Robert was responsive when we asked where to get firewood. We also enjoyed the Sturbridge coffee house and Maine Lobster (we liked it so much, we went twice)! We ended up going to the farmers market and flea market, which were great finds. Overall, a great stay with the kitchen utensils, bathroom necessities that you’d need. Close by the lake and a great neighborhood!
Guest favourite
Cottage in Brattleboro
4.97 out of 5 average rating, 32 reviews

On the Water at North Bridge Cove

StephRating, 5 stars4 weeks ago
2nd time staying here, lovely little spot on the river. Well-priced and met our needs. Best for 1-2 travelers and folks who either have a car or don't mind the easy walk into town. I'll likely stay here again when I next visit Bratt!
Top Guest favourite
Cottage in Amherst
4.98 out of 5 average rating, 83 reviews

Serene Modern Country Cottage near Amherst Center

DianeRating, 5 stars4 months ago
I stayed at the cottage for two nights with friends. It suited our needs well, providing a comfortable place for us to visit. The hosts were very accommodating and helpful. The nearby train did not seem to run over the weekend and we only heard it on Monday, late morning. Parking is definitely a little challenging in the snow but location is convenient and quiet. I would happily stay again if I am in the area.
Top Guest favourite
Cottage in Wilmington
5 out of 5 average rating, 38 reviews

Emerald Cottage @ Harriman Reservoir

EvanRating, 5 stars3 months ago
We really enjoyed our stay at Michelle’s place. Overlooking a lake in a peaceful location, this was perfect for a small group looking for a reasonably priced Airbnb to stay while skiing at Mount Snow. The location was cool and I can definitely see this house being great for warmer seasons as well. One thing that stood out was the clarity of instructions provided by the host. Both the description of the property and what to expect, and the check in/out instructions are very accurate and helpful.

Destinations to explore