Condo vacation rentals in Pioneer Valley

Find and book unique condos on Airbnb

Top-rated condo rentals in Pioneer Valley

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

%{current} / %{total}1 / 1
Top 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
4.95 out of 5 average rating, 62 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!

Superhost
A multi-story gray house is shown from the street, featuring a blend of modern and traditional architectural elements. Large windows line the front, with a porch accessible from the ground level. A well-maintained green lawn and several parked cars are visible in the driveway.
Condo in Hartford
4.92 out of 5 average rating, 25 reviews

Comfortable Relaxing Ideal Oasis

Beautifully, newly refurbished 2 Bedroom near downtown Hartford which is centrally located in Barry Square,10 mins away from Dunkin Donut Yard goat stadium 15 mins away from the blue back square, 19.9 miles or 32 minutes away from Bradley International Airport & Tweed New Haven located 36.9 miles or 49 minutes away, Waterbury Station 38 min drive 29.5 mi away, Hartford Convention center downtown, hospitals, Amtrak station, supermarkets restaurants and Bushnell park 4 min drive / 2.6 mi away.

Superhost
The living area features two comfortable sofas, one in a blue fabric and the other in a light gray. A round coffee table with a small plant sits in the center. A wall-mounted television is visible, and a dining area can be seen in the background.
Condo in Hartford
4.91 out of 5 average rating, 58 reviews

Your Home Away From Home

Welcome to Your Home Away From Home! This charming 1-bedroom apartment with a queen sofa bed in the living room, is nestled in the historic and vibrant heart of Hartford, offering the perfect combination of comfort, convenience, and local charm. The apartment features a spacious bedroom with a cozy queen-sized bed, and tasteful decor. The inviting living area is perfect for relaxing after a day of exploring the city. fully equipped kitchen and dining area. Each room is furnished with a 55” TV.

Guest favorite
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.
Condo in Hancock
4.92 out of 5 average rating, 13 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.

Superhost
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.
Condo in Hartford
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!

Guest favorite
A clean and inviting bedroom features a spacious bed with neutral bedding, accent pillows, and soft bedside lighting. Built-in shelves are displayed with decorative items, and a window allows natural light to brighten the area, complemented by light curtains.
Condo in Farmington
4.83 out of 5 average rating, 60 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

NEWLY UPDATED - Bright Spacious One bedroom condo in Farmington!! Convenient to airport (BDL)/bus/train transportation, Hartford (18mins), Miss Porters School (6mins), Avon Old Farms (7mins), UCONN HC (9mins), ESPN (20mins), the Hartford Mormon Temple (2mins). We are just a few miles off of route 84. Includes kitchenware & granite counter-tops, WiFi, and a HDTV. Restaurant (2mins) walking distance and many other amenities close by. Located in a quiet residential neighborhood with parking.

Superhost
A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.
Condo in Hancock
4.77 out of 5 average rating, 13 reviews

Ski-in/Ski-Out on Jiminy Peak

Jiminy Peak Mountain Resort is the perfect Berkshire get away surrounded by cultural attractions and with skiing, mountain biking, snow shoeing, mountain coaster, ropes course and MORE right on property! For an easy convenient trip once you arrive you will not have get back into your car. Jiminy Peak has everything you need on property bar/restaurants, ski/ snowboard shop, general store, ski/snowboard and snowshoe equipment rentals, ski/snow lessons and school, day care, souvenir shop.

Superhost
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.
Condo in Hartford
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

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.

Guest favorite
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.
Condo in Hartford
4.97 out of 5 average rating, 152 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!

Guest favorite
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.
Condo in Hancock
4.91 out of 5 average rating, 74 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Superhost
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
4.71 out of 5 average rating, 55 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 condo rentals

Destinations to explore