Condo holiday rentals in Pioneer Valley

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.

4.95 out of 5 average rating, 65 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!

A spacious living area features a light-colored sofa and an accent chair, with a coffee table centered on a patterned rug. Shelves display decorative items, while a television is mounted above a stone fireplace. Natural light enters through windows accented with blue curtains.

4.81 out of 5 average rating, 21 reviews

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed. Th

Top Guest favourite

A panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.

4.98 out of 5 average rating, 54 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

The living room features a spacious, light-colored sectional couch accompanied by decorative cushions and a comfortable throw. A glass coffee table sits centrally, while wall sconces provide soft lighting. Large windows dressed with sheer curtains allow natural light to fill the space.

4.8 out of 5 average rating, 30 reviews

Lovely two bedroom townhouse with parking

Enjoy a home-away-from-home experience at this centrally located place, close to downtown Hartford. This two bedroom townhouse offers everything you need for a comfortable stay, including a cozy living room, open concept kitchen, luxurious bedrooms, on site garage parking, and in unit laundry. This end unit townhouse is within walking distance to trendy restaurants, cafes, shops, entertainment venues, and some of Hartford’s most famous landmarks and attractions. Come enjoy an amazing stay!

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.

The exterior of a historic townhouse is displayed, featuring a brick pathway leading to the entrance. Lush greenery and vibrant yellow flowers frame the well-maintained garden, while ivy climbs the walls, adding to the charm of the property.

5 out of 5 average rating, 7 reviews

James Colt townhouse - whole apartment

This is for our whole apartment and is available rarely. If you don't see your dates on our calendar it doesn't hurt to ask! The guest room is listed separately. See note about cats, they will be in the house with you! Our condo is bright and spacious with wood floors and lots of light. Conveniently located, it’s an easy walk of everything in downtown Hartford. Located in a historic townhouse, our updated apartment is on the 1st floor and garden level and enjoys a private backyard

4.79 out of 5 average rating, 24 reviews

Spacious Condo • Quick Drive to Everything

Welcome to our urban retreat! This spacious 3-bedroom condo offers a stylish and comfortable haven within 5 minutes of W. Hartford and Downtown Hartford. With ample space and modern amenities, it's perfect for friends, family and business travelers seeking a convenient and relaxing stay. Enjoy the convenience of a full kitchen and ensuite laundry, just 5 minutes away from the Convention Center and Stadium. For your comfort, we provide complimentary cleaning for longer-term stays.

Condo in Litchfield County

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.

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.

Condo in Holyoke

4.75 out of 5 average rating, 4 reviews

3BR Apartment Near Holyoke Medical Center & Office

Conveniently located in Holyoke, MA, this spacious apartment offers a shared lobby area at the entrance, along with a private dedicated office/den area for your convenience. 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. The secure neighborhood is surrounded by various businesses and banks, ensuring a safe and convenient stay.

A spacious living area is highlighted by two large windows allowing natural light to fill the room. A dark leather sofa is paired with a wooden coffee table and a patterned area rug. A dining table made of wood is positioned nearby, alongside a console table with decorative items.

4.97 out of 5 average rating, 157 reviews

Posh Pad in The Business District

Truly unique, spacious, and comfortable condo in the heart of the Hartford Business District!!! Big city vibes in a quiet, cozy but swanky corner unit. Truly a home away from home. The unit is very nicely appointed with all the creature comforts you can imagine (+blackout curtains). The convenience of an Elevator makes grocery-hauling in the city very easy. Located within walking distance of the very best downtown Hartford has to offer!

A cozy living area is presented, featuring a sofa, armchairs, and a coffee table. Large windows offer natural light, framed by soft curtains. A mirror reflects the space, enhancing the openness. A small dining area with bar stools is situated adjacent to the kitchen.

4.92 out of 5 average rating, 25 reviews

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.