Condo holiday rentals in Pioneer Valley

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Top-rated condo rentals in Pioneer Valley

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Guest favourite
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!

Superhost
Condo in Hartford
4.82 out of 5 average rating, 33 reviews

Newly Renovated Clean Comfortable Relaxing Ideal

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
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
4.75 out of 5 average rating, 32 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

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
4.85 out of 5 average rating, 101 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.

Superhost
The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.
Condo in Hancock
4.61 out of 5 average rating, 162 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

A privately owned, older unit within Jiminy Peak's Country Inn. Located in the Berkshires, the inn is at the base of the ski slope. This unit is on the 1st floor of the last building which means you can ski to your doorstep if there's lots of snow (harder getting to the lift) . A locker room is at the end of the building to secure your equipment (key provided). The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and seasonal restaurants. Come enjoy the mountain!

Guest favourite
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
4.84 out of 5 average rating, 64 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.

Guest favourite
A bright living area features a comfortable sectional sofa and an elegant coffee table with a floral arrangement. Natural light enters from multiple windows, complemented by wall sconces. A flat-screen television is mounted above a modern wood-burning fireplace, creating a cozy gathering space.
Condo in Wilmington
4.96 out of 5 average rating, 28 reviews

10th Hole Haystack Golf Course in Wilmington VT

Kid Friendly 1550 sq ft 4 Bedroom condo on 10th Hole Haystack Golf course. 2.5 baths and indoor and outdoor wood burning fireplaces with wood onsite. 4 miles (11 min) from Mt Snow and less than 2 miles from downtown Wilmington VT. 9 total beds across 4 bedrooms - 2 kings, 1 queen, and 6 twins make this a perfect family or multiple families getaway. Snowshoeing or golfing on haystack golf course make this property functional in all seasons. Nest doorbell camera on front exterior

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.
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.

Top Guest favourite
Condo in Hancock
5 out of 5 average rating, 9 reviews

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

4-season Berkshires retreat at the base of Jiminy Peak Mountain. PRIME ski-in/ski-out in winter, mountain adventure park in summer & fall. The 3BR/2BA JPeak Condo at JJ's Lodge sleeps 8–10 (2 Queens, 2 Fulls, 2 Twins) — steps from ski lifts, trails, Alpine Slide, mountain coaster & summit chairlift. Country Inn amenities (pool, hot tubs, gym, game room) open year-round. Village restaurants, fire pits, coffee shop & ski shop open ski season.

Guest favourite
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.
Condo in Hancock
4.92 out of 5 average rating, 26 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.

Guest favourite
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, 82 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.

Top Guest favourite
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.

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