Cottage vacation rentals in Pioneer Valley

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Popular amenities for Pioneer Valley cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Great Barrington
4.94 out of 5 average rating, 295 reviews

Artist Cottage

ChadRating, 5 stars3 weeks ago
The Artist Cottage was a great secluded retreat. We loved how charming and cute the place looked. The colorful decor and charming antiques in the cottage made it feel special. The amenities were well taken-care of and we especially loved the hot tub, the outdoor fireplace, the spacious lodge, and the large, modern soaking tub. We enjoyed hanging out in backyard, where we could listen to numerous birds while sitting by a little waterfall in the morning. We appreciated the well-stocked kitchen. It was just a short walk from some nice hiking trails and we loved that it was only a short drive to town. Overall, we highly recommend this stay!
Top guest favorite
Cottage in Pownal
4.98 out of 5 average rating, 42 reviews

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

AlbertRating, 5 starstoday
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 favorite
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, 120 reviews

Northampton-area Hot tub Pet Friendly

ShannonRating, 5 stars4 weeks ago
A lovely retreat near Valley View Farm. Perfect if you have a dog who likes to explore Super clean, detailed instructions Thanks so much!!
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 favorite
Cottage in Otis
4.98 out of 5 average rating, 54 reviews

Berkshire lakefront cabin with modern luxuries

AileenRating, 5 stars6 days 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 favorite
Cottage in Lee
4.99 out of 5 average rating, 102 reviews

Charming Home in Lee

TerryRating, 5 stars6 months ago
Another perfect stay at Laurie's. This is our third stay over Thanksgiving week and we always are sad to leave. My family absolutely loves staying here. There is plenty of room to gather or to have some alone time. Beds are comfortable. Kitchen has everything you could need and is always pristine. Check in is stress free. Area is peaceful and serene. Lee is a lovely New England town. Downtown is less than a 5 minute ride. Many restaurants within a 5-20 minute ride. Outlets are 10 minutes away. Looking forward to our stay next year.
Guest favorite
Cottage in Williamstown
4.89 out of 5 average rating, 188 reviews

Cute Cozy Comfy Cottage in the Berkshires

KevinRating, 5 stars3 months ago
This little cottage is very comfortable. Its quiet and peaceful, but also provides easy access to local activities. You can just sit around and enjoy all the nature, or you can take a quick drive into town and go to some high quality museums or eat at a number of local restaurants. Its got a fenced in yard for the dogs as well as a bbq and firepit. This was our second stay and we would highly recommend it.
Guest favorite
Cottage in Warwick
4.95 out of 5 average rating, 38 reviews

By Still Waters Cottage

GilRating, 5 stars1 week ago
Just before we left for our short vacation, Daddy read to Mommy every night from a book about an enchanted April at the “San Salvatore” castle in Portofino, Italy. That was a magical place that touched the souls of its guests. So is the By Still Waters Cottage, which we now call “our San Salvatore” and plan to return to as soon as possible. --Sasha, a German Shepherd Mix rescue from Belarus; a world traveler, I look forward to frolicking again in Moore’s Pond.
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 favorite
Cottage in Brimfield
4.99 out of 5 average rating, 70 reviews

Cheerful 2 bedroom cottage with lake access.

KathleenRating, 5 stars2 weeks ago
This was the perfect spot for our mini vacation with our adult son and dog. The house was adorable and comfortable...the beds were especially comfy. The fenced in patio area and sun porch was so relaxing and although no one actually slept on it, the daybed was very comfortable as well. We enjoyed our day trip to Boston and multiple trips to Treehouse Brewery. Gwen's communication was awesome...such a terrific host! Hoping to stay again.
Guest favorite
Cottage in Canaan
4.85 out of 5 average rating, 172 reviews

Cozy Little Cottage

DouglasRating, 5 stars3 weeks ago
Gabriele's place was a great place to stay! We really liked the furnishings. When I messed up, Gabrielle was in constant touch with us so we could get everything right. She is a wonderful host
Guest favorite
Cottage in Cornwall
4.92 out of 5 average rating, 157 reviews

Newly Built Cottage in Housatonic Valley

KimRating, 5 stars3 days ago
I came to this area to hike the Appalachian Trail, and this place was just perfect for me. Lucy’s place is spotless, with tons of bright light and two great spots to sit outside and enjoy the nature. I loved that there was a French press available, and the bed was super soft, as well as the pillows. I also really liked the cozy squishy couch. The TV had streaming services, which was great for when I was working. I also spoke to a few neighbors who were passing by, and they were really friendly. They were kind enough to give me some suggestions for things to see in the area. I’m looking forward to visiting again!
Guest favorite
Cottage in Great Barrington
4.92 out of 5 average rating, 251 reviews

Cottage on Scenic Road

JeffreyRating, 5 stars2 weeks ago
We had a wonderful stay at this charming, comfortable, and clean cabin, with a nice yard for our dog. We especially loved sitting in the backyard listening to the birds…so peaceful! The location was perfect, close to a nearby town and some great antique stores. Would definitely recommend!

Private cottage rentals

Guest favorite
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 favorite
Cottage in Orange
4.99 out of 5 average rating, 79 reviews

Lake House with view of mountain

SoniaRating, 5 stars1 day 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 favorite
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.
Guest favorite
Cottage in Brattleboro
4.97 out of 5 average rating, 32 reviews

On the Water at North Bridge Cove

StephRating, 5 stars3 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 favorite
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!
Top guest favorite
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.
Guest favorite
Cottage in Wendell
4.99 out of 5 average rating, 79 reviews

Cozy Scenic Cottage on Small Pond, Near Lake Wyola

SheaRating, 5 stars6 days ago
We loved our stay at Laurie’s cabin! It’s a very comfortable, peaceful space close to several great nature trails. The cabin is in a rural setting & has a lovely yard next to a little pond. The property is also adjacent to a beautiful conservation area with lots of birds & wildlife. The cabin is really nice inside with lots of windows, cozy eating & sitting areas, wifi & steaming tv, a shower with good water pressure, & a well-stocked game & book shelf. Laurie left guides & instructions for everything so it was really easy to get settled in! This will be my first choice for lodging if I’m staying in the area again- it was a perfect base of operations for our visit.

Destinations to explore