Apartment holiday rentals in Pioneer Valley

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Pioneer Valley

Guests agree: these apartments are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Superhost
Apartment in Wilmington

Crafts Inn in Vermont 1br suite, Saturday check-in

This offer is for a 7 Night Stay only from Saturday to Saturday. All other requests cannot be accommodated. For year-round outdoor sports and gorgeous scenery, try the Crafts Inn, which was designed in 1898 by Stanford White and is now registered as a National Historic Landmark. The Crafts Inn provides an indoor pool, racquetball court, and saunas. The Mount Snow ski area is within 6 miles. In addition to the average annual snowfall of 15 feet, snowmaking ensures plenty of snow from mid-Nove

The living room features a spacious light-colored couch with decorative pillows and an accent ottoman. A large artwork adorns the wall, while a plant adds greenery to the space. Natural light enters through two windows, complementing the modern decor.
Apartment in Springfield
4.83 out of 5 average rating, 12 reviews

5 Bedrooms Mins to Six Flags, MGM, & Hospitals

Enjoy a modern 2nd floor condo in a private setting. The 5 bedroom 2bath( 1shower, 1tub) condo is elegantly styled, embracing style and functionality. It has everything you'll need to enjoy, relax, recharge, or work during your Springfield area stay. Clean, comfortable, family, friendly , safe and as pictured. You will have the entire place to your self. Safe neighborhood full of families with diverse background. Second floor unit with 12 steps up to the entrance. Furnished back yard .

Apartment in Holyoke
4.86 out of 5 average rating, 7 reviews

Steps to Holyoke Medical Center! Remote-Work Hub

Great for School Visits & College Tours | Easy I-91 Access | 11 Mi to The Big E Experience the heart of the Knowledge Corridor from this modern Holyoke vacation rental! Whether you're in town for business or leisure, this spacious apartment offers a secure retreat perfectly nestled between Springfield and Northampton. After a day of meetings or exploring Mount Tom State Reservation, head to downtown Holyoke for dinner and boutique shopping. Lock in your Western Massachusetts getaway now!

Guest favourite
Apartment in Amherst
5 out of 5 average rating, 9 reviews

Two story condo near Amherst town center and UMass

Located within minutes of downtown Amherst, our condo offers a convenient location with grocery stores, restaurants, and nearby colleges like UMass, Amherst College, and Hampshire College. A bus stop in front of the complex provides freedom and convenience, allowing you to avoid the hassle of finding parking spaces while heading to town or nearby colleges. Most bus services in the Amherst area are free. The condo has a coin-operated laundry in the common basement, also nearby Laundromats.

Apartment in Springfield
4.96 out of 5 average rating, 26 reviews

1 Mi to MGM Springfield: Cozy Winter Duplex!

Open-Concept Layout | WFH Friendly | Gas Grill | 3 Mi to The Big E Embrace a New England winter at this bright and welcoming 4-bed, 2-bath vacation rental duplex in Springfield. After a day of casino fun at MGM Springfield, exploring festive downtown events, or skating at local rinks, return to a warm and comfortable home base perfect for families and groups. You can also enjoy easy access to nearby colleges and universities, and holiday happenings. Book your snowy season getaway today!

Superhost
A bright and spacious bedroom features a large bed with soft bedding, complemented by two bedside lamps. A wooden bench sits at the foot of the bed, and a dedicated work desk is positioned near a window, allowing natural light to fill the room.
Apartment in Simsbury

Luxury furnished condo. Attached garage. Fireplace

Welcome to the luxurious Simsbury retreat designed and fully equipped for displaced or relocating families and traveling professionals. Our townhouse offers 2 bedrooms with en-suite bathrooms, an attached garage, huge basement/TV/Game room, fully stocked kitchen with granite countertops, and large deck. Equipped with brand new luxury furnishings, a cozy gas fireplace, TVs and desks in each room, 2 bikes and games, it is perfect for indulging in comfort and convenience during your stay.

An outdoor view of a lively resort features a large swimming pool surrounded by sun loungers, with families enjoying the water. Nearby, tennis courts are visible, and a mini-golf course is positioned in the foreground, blending seamlessly with the natural landscape.
Apartment in Lee
4.82 out of 5 average rating, 38 reviews

Holiday Inn Club/ Oak and Spruce, Berkshires

This resort is the Holiday Inn Club at Oak and Spruce. The rooms have been greatly upgraded since I took these pictures. I own time shares here. It is a wonderful resort with so many amenities and the most perfect location, 15 minutes from Tanglewood, 10 minutes from center of Stockbridge. You can look it up for better photos on the web site. It is on a country road but near everything and well furnished and stocked. Reservations must be made at least 30 days in advance.

Guest favourite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Apartment in Litchfield County
4.93 out of 5 average rating, 30 reviews

Meadow View

Nestled on a quiet country road, Pacer's Pasture has everything you need for a rejuvenating stay. Just over a mile away, Haystack Mountain State Park offers scenic hiking; while the Station Place Cafe and Norfolk Pub are great eateries to enjoy dinner before catching a concert at Infinity Music Hall -- right in Norfolk. The Berkshire Country Store, an antique store, and a liquor store offer nearby provisioning and shopping. The Yale Music School is less than a mile away.

A light-filled lounge area features a cozy sofa adorned with patterned cushions and a coffee table made of distressed wood. A flat-screen TV is mounted on the wall, and a stylish chandelier provides overhead illumination, enhancing the room's inviting ambiance.
Apartment in Suffield
4.77 out of 5 average rating, 13 reviews

Historic Estate Studio Loft

EASTWOOD ESTATES – THE LOFT SUITE IDEAL FOR: • Remote Workers & Digital Nomads • Short-Term Stays & Solo Retreats • Quiet, Low-Key Staycations *Note: Stair access required – not recommended for children or guests with mobility concerns FLOORPLAN & SLEEPING ARRANGEMENTS Compact, Elevated Living • 2 Full Beds (Main Level) • Pull-Out Sofa for Extra Guests • Cozy Upper Loft Nook • 1 Full Bathroom • Access via Single Interior Staircase

Apartment in Holyoke
4.33 out of 5 average rating, 3 reviews

Work, Play & Stay! Apt Near Holyoke Medical Center

Conveniently located in Holyoke, MA, this modern apartment offers a comfortable stay with a shared lobby area at the entrance. Situated across the street from Holyoke Medical Center and near Interstate 91, this home is centrally positioned between the bustling cities of Springfield and Northampton. Safety is a top priority in this secure area, surrounded by various businesses and banks, providing peace of mind for guests.

Apartment in Windsor

Modern 1BR • 10 min to BDL Airport• Free Parking

“Welcome to your modern Windsor retreat! This newly renovated 1BR, 1.5-bath condo is minutes from Bradley Airport and Hartford. Enjoy a cozy living room with smart TV, full kitchen, King bed with blackout curtains, and a rare extra half bath. On-site laundry, free parking, seasonal pool, and a walkable plaza with Target, dining, and more.

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.
Apartment in Adams
4.73 out of 5 average rating, 59 reviews

Downtown Adams Vintage Getaway

Your family will be close to everything when you stay at this centrally-located place. Walk to the Adams Theater, rail trail, grocery store, restaurants, shops, or take a quick drive to MassMoCA, Jiminy Peak, or Greylock Glen. This is the perfect location for all north county has to offer. One free parking spot in back of building.

Popular amenities for Pioneer Valley apartment rentals

Destinations to explore