Condo vacation rentals in Pioneer Valley

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Top-rated condo rentals in Pioneer Valley

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Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.94 out of 5 average rating, 71 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

The exterior of a two-story white house is displayed, featuring orange shutters and a well-maintained front garden. Steps lead up to a central white door, framed by a welcoming wreath. A balcony is visible on the upper level, providing outdoor space.
Condo in Winchendon
4.57 out of 5 average rating, 53 reviews

Private 1st Floor Apt @ Winchendon Center Town

Beautiful Cozy 2 bedrooms apartment. One queen bedroom, one full size bedroom and 1 bathroom. Strategic located in Winchendon center town. Steps away from RT 12, Rt 140, Rt 2 and RT 202. Minutes away from Rindge, Jaffrey and Keene. Close to Otter River Park, Camp Dennison, Contookock beach, Lake Monadnock, Tully lake and Doanes falls. This place is designed for commuters, traveling to visit family and businesses trips. Or simply decompress, escape from the routine and relax. Come and reserve.

Superhost
Condo 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

Guest favorite
Condo in Holyoke
4.89 out of 5 average rating, 9 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 favorite
Condo 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.

Guest favorite
Condo in Springfield
4.97 out of 5 average rating, 29 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.
Condo 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.

Guest favorite
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.
Condo 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 lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.
Condo in Lenox
4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshires. With a scenic pond view and surrounded by breathtaking mountains, this charming unit is perfect for couples or small families seeking tranquility. Enjoy a fully equipped kitchen, warm fireplace, and access to indoor and outdoor pools, along with endless nearby hiking trails and cultural activities. Your perfect getaway awaits in beautiful Lenox, MA.

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.
Condo in Springfield
4.83 out of 5 average rating, 12 reviews

5BR 2-Level Duplex Sleeps Groups | Covered Porch

Spacious 5-bedroom, 2-level duplex perfect for families, work groups, and extended stays. Designed for comfort and group travel, with plenty of space to relax, dine, and unwind. ✨ Highlights 5 bedrooms (including 1 king bed) TVs in every bedroom 2 full bathrooms (tub + walk-in shower) Dining table seats 8 Fully equipped kitchen In-unit washer & dryer Covered furnished porch Second floor unit with 12 steps up to the entrance. Furnished back yard .

Top guest favorite
A modern kitchen is visible, featuring stainless steel appliances and ample storage cabinets. A dining table set for four is in the foreground, complete with glassware and decorative green accents. Natural light fills the space, highlighting the open floor plan that leads into the living area.
Condo in Lenox
4.9 out of 5 average rating, 84 reviews

Heart of Lenox!! - Renovated downtown apartment

Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road you will find the historic Red lion Inn in Stockbridge or Norman Rockwell Museum.

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.
Condo 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.

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