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

Private room in Dover
4.81 out of 5 average rating, 16 reviews

Crosstown Ski House sleeps 4 to 7+

PatrickRating, 5 stars14 months ago
Jaime is the consummate Airbnb host. She is kind, friendly, and a joy to converse with. The accommodations are exactly as described – the downstairs floor of her townhouse, with full access to the second floor living room and kitchen. The townhouse is less than a mile from the Mt. Snow parking lots and the rental is bargain-priced for the area. Jaime is a connoisseur of quirky art and artifacts, and the walls are resplendent with that quirkiness. I love staying there.
Apartment in Dover
4.6 out of 5 average rating, 5 reviews

Charming condo close to Mt. Snow

YuwenRating, 5 stars14 months ago
The host is really nice and flexible to our schedule
Superhost
Private room in Lenox
5 out of 5 average rating, 7 reviews

Tranquil Church Apt Lenox MA - 1 BD

DouglasRating, 5 stars1 day ago
It is a lovely, roomy apartment. Almost everything we could have needed was supplied. Only additional thing we could have used was shampoo, otherwise all cleaning supplies, and spare linens we plentiful. Instructions were mostly clear, but in the end I couldn't find where to leave the trash. We've been spending a spring weekend in Lenox for almost 30 years, so we know the area and the amenities. The location of this space is ideal.
Apartment in Dover
4.71 out of 5 average rating, 14 reviews

2BR | Balcony | Fireplace | Washer/Dryer

HeileRating, 5 stars2 months ago
Loved staying here! Hopefully we can come back next year!
Apartment in Dover
4.71 out of 5 average rating, 14 reviews

2BR Cozy condo w/ wood-burning fireplace, deck

GundaRating, 5 stars1 month ago
Perfect, simple but clean condo for a ski weekend. Location is great for skiing Mt. Snow, but otherwise there seemed to be nowhere to go for a walk. Condo is practical, clean but quite dark. Patio does not seem to be used. All necessary appliances and basic cooking supplies were there. Great ski weekend accommodation!
Apartment in Springfield
4.92 out of 5 average rating, 13 reviews

Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!

ChandlerRating, 5 stars1 week ago
Our stay was everything we hoped for and more! We stayed while we were exhibiting dairy cattle nearby at the Eastern States Expo grounds, and it was a lot of late nights and early mornings. The location was super close to the grounds but still in a quiet neighborhood, plenty of parking, and felt safe walking from the car to the front steps each night. I had a little trouble locking the door the first time we left so I called the host before 7 am and they answered immediately, and were friendly and helpful (not at all grumpy about the early am call!!). The house was immaculate and had everything we needed and then some. I would absolutely recommend this rental and am looking forward to booking ahead for next year!
Apartment in Dover
4.53 out of 5 average rating, 40 reviews

Rare condo 5 min to Mt. Snow, 2BR, 2BA Sleeps 6

PeterRating, 5 stars3 months ago
Great place to stay for a ski trip. The unit is a bit older, but clean and functional. The host helped coordinate retrieving items left behind after checkout. Greatly appreciated.
Apartment in Charlemont
4.82 out of 5 average rating, 17 reviews

Berkshires Getaway < 1 Mi Skiing & Hiking!

JohnRating, 5 stars3 months ago
Had an amazing stay! The location couldn't be better for skiing at Berkshire East—it’s literally just across the parking lot, which made it so easy to get on and off the slopes. The house itself was super warm and cozy, perfect for relaxing after a day on the mountain. The kitchen was well-equipped, so we were able to cook up some great meals without any issues. Definitely planning to stay here again next time we're skiing at Berkshire East! Highly recommend!

Pet-friendly apartment rentals

Guest favourite
Apartment in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars4 months ago
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!
Private room in Northfield
4.47 out of 5 average rating, 66 reviews

A Healing Forest Space in the Heart of New England

FranRating, 5 stars5 months ago
This is that one-of-a-kind place. Nestled in the woods, unusually designed and arranged house that makes for a unique experience. Plus, Joseph is a most interesting and engaging host. We're so glad we found it.
Apartment in Enfield
4.4 out of 5 average rating, 10 reviews

Entire house - 4 Bedroom-Enfield

HunterRating, 5 stars5 months ago
Everything I needed for my work trip👍👍👍 Clean and cozy stay
Superhost
Apartment in Hartford
3.75 out of 5 average rating, 4 reviews

Beautiful 2 bedrooms/ 2 bath Condo

BrentRating, 5 stars115 months ago
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.
Guest favourite
Apartment in North Adams
4.96 out of 5 average rating, 71 reviews

Newly renovated 2BR on historic Eagle Street.

ShellyRating, 5 stars3 weeks ago
We loved staying for the weekend at Katie’s place. We walked to great restaurants and Mass MOCA museum. So cozy and relaxing all around!
Apartment in Charlemont
4.73 out of 5 average rating, 11 reviews

Charlemont Airbnb Center With Four mor bedrooms

AndrewRating, 5 stars7 months ago
David’s place was just as described. Perfect for my one night stay for a wedding near by.
Apartment in Dover
4.67 out of 5 average rating, 18 reviews

Mt Snow condo with ski home trail!

JohnRating, 5 stars4 months ago
Just as advertised. Really convenient to get to the mountain and ski. Perfect stay, thank you.

Apartment rentals with a pool

Apartment in Dover
4.77 out of 5 average rating, 13 reviews

Spacious 3BR | Deck | Pool | Washer/Dryer

GabriellaRating, 5 stars4 months ago
This place is great if you are headed to Mount Snow with a large group. It is a fair price for the large size and slightly dated place. There is plenty of space for and it has a cute log cabin style. The hot tub was on and ready to use which is awesome. It is not the most updated place, but given the price, this is definitely worth what you pay for!
Apartment in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars15 months ago
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+
Superhost
Apartment in Hancock
4.87 out of 5 average rating, 31 reviews

Jiminy Peak Apartment

SandyRating, 5 stars2 months ago
Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.
Apartment in Dover
5 out of 5 average rating, 4 reviews

Cozy Townhome by Mt Snow with Ski Home Trail

ChloeRating, 5 stars34 months ago
We had a nice long-term stay at Beth and Kyles's condo while renovating our home. The location is great for Mt. Snow activities. They are pretty hands-off hosts which was fine for us, but might be difficult for some. There is a nice stand-up desk for working from home that I utilized frequently. The condo has internet and for the most part it worked well, but it could be a bit spotty during video calls, so I'd recommend having a back-up plan if video calls are part of your time here. We definitely enjoyed being able to utilize the pool and clubhouse that the condos have access to, and overall enjoyed our stay.
Superhost
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars14 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Destinations to explore