Cottage vacation rentals in Pioneer Valley

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Popular amenities for Pioneer Valley cottage rentals

Cottage rentals with a hot tub

Top guest favorite
Cottage in Lanesborough
5 out of 5 average rating, 18 reviews

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

KerryRating, 5 stars2 months ago
Darcy is a top host. We loved the in-wall USB chargers and the bluetooth speaker, the welcoming wine, the beautiful layout and decor, the cozy feeling with lots of space for us to sprawl out and the high quality of the renovation. I felt secure and cozy and everything from the hot tub to the sheets were super clean and fresh. We will be back in the summer for kayaking on the lake. Thank you Darcy!
Cottage in Monterey
4.68 out of 5 average rating, 19 reviews

mountain refuge

JoshuaRating, 5 stars3 weeks 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!
Top guest favorite
Cottage in Burlington
4.98 out of 5 average rating, 100 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

GenesisRating, 5 stars2 days ago
Feyza was an excellent host! Very helpful and responds really quick. I planed a surprise birthday for my bf and with her help, she decorated the house perfectly! The house was beautiful with very amazing views of the lake. Very quiet and peaceful and lots of restaurants near by.
Superhost
Cottage in Norfolk
4.93 out of 5 average rating, 15 reviews

The Cottage at Blackberry River Inn

RohitRating, 5 stars3 weeks 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
4.71 out of 5 average rating, 119 reviews

Northampton-area Hot tub Pet Friendly

AkashRating, 5 stars3 weeks ago
Our host was extremely helpful and pleasant to all our questions, and the accommodations were comfortable with all the amenities of a normal home, plus a very pleasant and private hot tub. Would stay here again.
Superhost
Cottage in Great Barrington
4.84 out of 5 average rating, 37 reviews

THE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!

MaureenRating, 5 stars1 month ago
A large, lovely, comfortable home, (comfy beds, plush, plentiful linens) in a great location! Loads of room for six adults, two kids and our pup. We want to make it a yearly event!
Top guest favorite
Cottage in Otis
4.98 out of 5 average rating, 48 reviews

Berkshire lakefront cabin with modern luxuries

VictoriaRating, 5 stars1 month ago
We had a wonderful stay. The cabin is located in a beautiful, peaceful area and has all of the amenities one could want. Our original plan was to explore the surrounding area but we ended up spending our whole trip in the cabin because it was so lovely. Matt was a great host and very responsive. Highly recommend!
Top guest favorite
Cottage in Pownal
5 out of 5 average rating, 37 reviews

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

RyanRating, 5 stars2 weeks ago
Besides this couple being accommodating, they also added a bunch of little extras. everything was super clean in the view from the hot tub was great at night. I will definitely go back!

Pet-friendly cottage rentals

Superhost
Cottage in Orange
4.89 out of 5 average rating, 111 reviews

The Film Shack: A Sweetwater Stay

DillonRating, 5 stars1 month ago
Amazing place quiet cozy and amazing views would definitely stay again most amazing views quiet peaceful tranquil
Guest favorite
Cottage in Orange
4.93 out of 5 average rating, 170 reviews

The Lake Cottage: A Sweetwater Stay

KarinRating, 5 stars2 weeks ago
Very clean and comfy place, I had a great time getting away from my busy life for some reading, listening to music, and just looking out at the lake. Would definitely recommend!!
Guest favorite
Cottage in Sharon
4.92 out of 5 average rating, 165 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

ElisaRating, 5 stars1 month ago
Lovely cottage, lovely hosts. Kid-friendly and super clean! Felt very private, yet when I ran out of milk they happily dropped off some cream for my morning coffee 🙏 Beautiful views and an extra treat was seeing the chickens in the morning. Perfect location for skiing.
Superhost
Cottage in Chesterfield
5 out of 5 average rating, 3 reviews

Cottage on Spofford Lake “Barn”

ChristopherRating, 5 stars5 months ago
The cabins were terrific. We had three cabins as a group. They are across the street from Spofford Lake, which has a small beach and a dock. We had a terrific night hanging out on the beach while lighting a fire in the pit. We had a great visit at Copper Cannon Distillery (located down the road) and went on a few hikes.
Guest favorite
Cottage in New Marlborough
4.92 out of 5 average rating, 37 reviews

Peaceful Berkshires Ski Cottage in the Woods

NealRating, 5 stars2 weeks ago
Ayren was great. very responsive and accommodating. The house was cozy, had everything we needed, and close to the ski slopes! Would definitely stay again if in the area.
Guest favorite
Cottage in Windsor
4.9 out of 5 average rating, 185 reviews

In-law apartment in Farmington River Cottage

CarlieRating, 5 stars1 day ago
Great place great hospitality really loved the stay she was really nice I would 100% book again she is just the most sweetest person I’ve met !
Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 66 reviews

Cheerful 2 bedroom cottage with lake access.

DonalRating, 5 stars2 months ago
This place is bright with lots of natural light. Well equipped with very nice sun room and patio. Close to Old Sturbridge Village where the Christmas show was excellent. We had a relaxing and cozy dinner at the Duck. Gwendolyn was a gracious host keenly attentive to our arrival, weather, comfort and more. You will enjoy the cottage.
Guest favorite
Cottage in Granby
4.89 out of 5 average rating, 187 reviews

The Little Red Schoolhouse ~ Circa 1877

CraigRating, 5 stars2 weeks ago
The Little Red Schoolhouse was perfect! Easy self check-in, spotless place, easy-to-follow instructions, easy parking in the driveway (well plowed in the snowy winter), easy checkout, responsive host, cozy space, comfy beds, good heat, multiple living room spaces, a well stocked kitchen, and a peaceful location. I'm staying here every time I visit northern Connecticut! A++++

Private cottage rentals

Superhost
Cottage in Great Barrington
4.76 out of 5 average rating, 78 reviews

Ski Cottage with fireplace in the Berkshires

KennethRating, 5 stars1 month ago
Only thing I could say is bring slippers. In the morning, your toes are a little cold, in the middle of winter when it is really cold outside. I respect there no shoe policy.
Guest favorite
Cottage in Stockbridge
4.94 out of 5 average rating, 34 reviews

Quiet 2 BR cottage in the heart of the Berkshires

CatherineRating, 5 stars6 months ago
Perfect spot for a peaceful, relaxing Berkshires weekend and/or visit to Tanglewood. Beautiful location of the cabin among the trees, super convenient to lots of hiking, cute towns to wander with great food, and town beach for swimming. And, couldn't be better situated for catching a show at Tanglewood. Sonia was also helpful, responsive, and friendly about all of the preparation details and made the logistics of the trip simple.
Superhost
Cottage in Hancock
4.84 out of 5 average rating, 80 reviews

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

KeehoRating, 5 stars3 months ago
Had an amazing experience staying at Renee’s beautiful cottage. It’s quiet and tucked away but very accessible from the main roads. I highly recommend staying here if you want a cozy getaway with all the amenities you’d need for a comfortable and enjoyable stay. The fireplace was definitely the highlight of the cottage.
Superhost
Cottage in New Marlborough
4.85 out of 5 average rating, 39 reviews

All Season Cottage near Gt Barrington, ski areas

LindaRating, 5 stars3 months ago
I have stayed in this little house several times, and it always seems like the perfect place., not matter what the season. The yard and surroundings are lovely and the house itself is cozy and beautifully maintained. The host is always so responsive and helpful.
Guest favorite
Cottage in Holland
4.95 out of 5 average rating, 82 reviews

Cozy Lakefront Cottage

JohnRating, 5 stars4 months ago
Lovely rustic cottage on a picture perfect lake. Dawn was a wonderful host and made sure we had everything we needed to enjoy our stay. Will stay again!
Guest favorite
Cottage in Lanesborough
4.97 out of 5 average rating, 64 reviews

Amazing 2 bedroom lake front cottage, large patio

JulieRating, 5 stars4 months ago
The views of the lake and fall foliage during our stay were breathtaking! The full moon rising over the lake was stunning too. The deck and living areas all offered amazing light and views. The kitchen was great and we ate most meals there but also enjoyed Zucchini and Proprietors Lodge restaurants nearby. Location was ideal for day trips north and south to Mt Greylock, N Adams, Lenox, and Great Barrington. It was a wonderful stay for us and we’d love to return.
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars5 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 Shutesbury
4.92 out of 5 average rating, 219 reviews

Lake Wyola House Shutesbury Massachusetts

JennyRating, 5 stars4 months ago
We felt so comfortable and relaxed. Bob’s home had everything we needed for our stay, including plenty of fun games for the kids. The neighborhood is perfect for a family vacation. We hope to be back in the future!

Destinations to explore