Apartment holiday rentals in Pioneer Valley

Find and book unique apartments on Airbnb

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Popular amenities for Pioneer Valley apartment rentals

Weekly apartment rentals

Top Guest favourite
Apartment in Northampton
4.93 out of 5 average rating, 105 reviews

Warm & Stylish Apartment w/laundry - walk to DT

PaulRating, 5 stars5 days ago
Very enjoyable stay, very close to downtown and stores. Nice property and a responsive host.
Superhost
Apartment in Northampton
4.89 out of 5 average rating, 215 reviews

2 bedroom apartment in the heart of downtown

KatherineRating, 5 stars3 days ago
A great spot in the heart of downtown Northampton. We visited to attend the Back Porch Festival, and all events were in easy walking distance. The apartment was clean, well stocked, and comfortable. We hope to visit again!
Guest favourite
Apartment in Wilmington
4.98 out of 5 average rating, 476 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

MariaRating, 5 stars3 weeks ago
Always a great stay at Happy Hour! Our favorite spot.
Guest favourite
Apartment in Hartford
4.91 out of 5 average rating, 45 reviews

Mod-Chic 1 Bedroom with Free Parking & Wifi

TimRating, 5 stars1 week ago
My first personal experience staying at an Airbnb was wonderful. However, the pictures did not accurately reflect what I found when I entered. The personal touches throughout the apartment made my stay very enjoyable and exciting. Thank you Oomi.
Top Guest favourite
Apartment in Vernon
4.96 out of 5 average rating, 157 reviews

Farm land view.

LoisRating, 5 stars5 days ago
Great stay, as usual. Peter is a friendly and responsive host. Unit is always clean and has all the necessities.
Top Guest favourite
Apartment in Torrington
4.98 out of 5 average rating, 160 reviews

Apartment on Main St.

GeneRating, 5 stars2 months ago
Molly's place was GREAT--a total gem for the area. The vibe and layout of the space was sunny, peaceful, and super welcoming. Easily one of my favorite AirBnB's ever--we will definitely be back! The kitchen had everything we needed and the whole apartment felt spacious and roomy, yet cozy. The backyard area is gorgeous! Even though the house is right on main street, the sound isolation was great and we slept well every night we were there (the most comfortable bed EVER also helped). We miss this place already!!
Guest favourite
Apartment in Guilford
4.88 out of 5 average rating, 402 reviews

Apartment with a view

BenRating, 5 stars1 month ago
I had a great experience staying here! I booked it last minute, and it turned out to be a perfect choice. The space was comfortable and had everything we needed for a pleasant stay. The area was quiet, making it easy to relax. The host was also very responsive and accommodating, which made the whole experience smooth and stress-free. I would definitely stay here again!
Top Guest favourite
Apartment in Simsbury
4.99 out of 5 average rating, 322 reviews

Ensign House Room

NancyRating, 5 stars1 week ago
This is the second time I've stayed in the little apartment at the Ensign House. It's a peaceful and quiet place to stay while visiting my boisterous family in Simsbury. I found it cozy and well heated and so much nicer than a motel room. It's a quick walk to a little shopping center with a grocery and drug store. You do have the downtown street and parking lot lights at night. There are blackout shades in the windows but I prefer to leave them open for the morning light.

Private apartment rentals

Top Guest favourite
Apartment in North Adams
4.98 out of 5 average rating, 101 reviews

Charming Art Filled Apartment

JakeRating, 5 stars1 week ago
It was a very cozy spot. Lovely array of artwork in every room. Very close to Mass MoCA and downtown restaurants.
Guest favourite
Apartment in Brimfield
4.91 out of 5 average rating, 136 reviews

Lovely one bedroom apartment with own entrance

ZackeryRating, 5 stars4 months ago
Great private place to stay. Accommodations were exactly as listed in the description. Very friendly host with great recommendations nearby.
Top Guest favourite
Apartment in Canaan
4.99 out of 5 average rating, 134 reviews

West Main

KamariaRating, 5 stars1 month ago
thank you Shirley your home is beautiful and quaint it made my birthday weekend a wonderful time ♥️♥️
Top Guest favourite
Apartment in Brattleboro
4.9 out of 5 average rating, 356 reviews

Quiet St in Town, gardens, terrace

BrendanRating, 5 stars3 weeks ago
This is a clean and cozy in-town top floor apartment - within walking distance of Main St, the Brattleboro Food Co-op and many local eateries, coffee shops and excellent shopping opportunities. The apartment is nicely decorated, and we loved the closed in sun-porch for gearing up to go outside since this was mid-winter during a cold snap.
Guest favourite
Apartment in Williamsburg
4.88 out of 5 average rating, 209 reviews

Studio apartment on route 9, "Inn the Valley"

FrancesRating, 5 stars1 month ago
I recommend the Williamsburg studio with hosts Robin and Bud. The apt is in the end of the Williamsburg Animal Clinic and I was afraid we’d hear barking dogs but it’s quiet, private, lovely and perfectly clean. It’s on the main road but you can’t hear traffic once inside either. The bed is high with a good mattress and we slept well, and it’s a short drive to the Bread Euohoria restaurant as well as the Williamsburg General Store. Charming place - we plan to go back. Fran
Guest favourite
Apartment in Northampton
4.96 out of 5 average rating, 306 reviews

Roost House (2 BR Apt. downtown)

AlanRating, 5 stars3 weeks ago
As others have described, the location is superb - close to the center of everything in downtown Northampton - and the apartment is clean and well appointed. The owner is very responsive and helpful, her instructions were clear, and she even arranged for us to access the apartment a tad early which was much appreciated. We were fortunate that the cleaning person was present when we arrived during a heavy snowstorm and helped us haul our luggage up the exposed outside stairs. It was a snowy and icy weekend, so the steps were particularly difficult to negotiate. We are an older couple (though we traveled there hoping to X-country ski) and generally don’t mind carrying our own luggage up flights of stairs, but we needed a bit of extra help this time. That matter aside, we thoroughly enjoyed our stay at Robyn’s roost and would happily consider staying there again…preferably in finer weather. P.S. The owner kindly arranged to have the driveway plowed during our stay.
Guest favourite
Apartment in North Adams
4.91 out of 5 average rating, 444 reviews

Private guest apartment. One block from downtown.

AlessiaRating, 5 stars1 month ago
Cozy apartment, the kitchen is stocked with any kind of goodies to make you feel welcome! Thank you
Guest favourite
Apartment in Amherst
4.92 out of 5 average rating, 242 reviews

Woodsy hideaway apartment

KacieRating, 5 stars2 weeks ago
A cozy stay for my partner and I to spend a few days relaxing on our winter break. Lots of great food, shopping, and things to do in the area. Deb was very kind, thoughtful, and proactive. I will totally stay here again if I book another appt at Elements Hot Tub Spa. :)

Apartment rentals with a hot tub

Top Guest favourite
Apartment in Amherst
5 out of 5 average rating, 21 reviews

The View Guest Suite - Amherst

JanetRating, 5 stars1 month ago
Beyond delightful to stay here! The layout is perfect for two couples. The space is pristine, all the amenities you need, and then some really thoughtful and special touches that made us feel so welcome. We hope we can make it back again some time!
Guest favourite
Apartment in Hancock
4.97 out of 5 average rating, 35 reviews

Ski-InSki-Out Loft Lift&MT.Views

ChangRating, 5 stars3 weeks ago
Amazing location, right in the heart of Jiminy Peak village. The unit was clean and cozy. Colin was prompt and clear with his instructions.
Guest favourite
Apartment in Sandisfield
4.96 out of 5 average rating, 50 reviews

Sweet Dreams Retreat

LoriRating, 5 stars3 weeks ago
We can’t say enough good things about Sweet Dreams Retreat. It was the coziest, most relaxing stay and Melissa absolutely went above and beyond. We felt so at home. We loved the hot tub, fireplace, and all the beautiful amenities. The attention to detail is incredible - you can tell everything in the home was very well thought out to help guests enjoy their stay. It’s only 20 minutes from town where you can enjoy a bunch of cute shops and restaurants. Melissa provided amazing local recommendations that we absolutely loved as well. We hope to come back very soon! Would highly recommend Melissa’s home to anyone looking for a relaxing getaway in the Berkshires! There’s absolutely nothing like it. :) Thank you Melissa and Geoff for your amazing hospitality!
Superhost
Apartment in North Adams
4.76 out of 5 average rating, 87 reviews

The Crystal Loft

PatrickRating, 5 stars2 weeks ago
Had a great stay at this airbnb, very clean space overall. Super cool geodes and rocks all around the space. Lastly, the hot tub was warm and clean and ready for us as soon as we checked in. Couldn’t ask for more, the place was warm with adequate blankets pillows and towels.
Superhost
Apartment in Guilford
4.92 out of 5 average rating, 60 reviews

Nasuta Hills (Lower Level)

RileyRating, 5 stars3 days ago
We had a great stay at Nasuta Hills! Dan was always responsive and the 10 minute drive to the restaurants and stores in Brattleboro was very convenient. Would definitely come back again!
Top Guest favourite
Apartment in Chicopee
5 out of 5 average rating, 18 reviews

Homey 2nd floor 2 bedroom apartment

AliciaRating, 5 stars5 months ago
This is our 4th time staying with Sandra and it still is perfect! Very homey, fully equipped with all your needs plus some, easy parking, check and check out, comfy beds, this list goes on.. and Sandra is the best host ever!!!! Very friendly and accommodating. Highly recommend. Looking forward to our next stay! Thanks Sandra! 😃
Superhost
Apartment in Hancock
4.71 out of 5 average rating, 17 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

HershyRating, 5 stars6 months ago
place is nice. perfect location. just a snow ball away from all attractions
Guest favourite
Apartment in Pittsfield
4.83 out of 5 average rating, 72 reviews

*Berkshire's Sweet Spot 2-Close to ski/Spa open

AnnaRating, 5 stars6 months ago
Great location, near many Berkshires attractions. The hot tub and pool were great! Welcoming gifts of snacks and wine were much appreciated.

Destinations to explore