
Condo holiday rentals in Pioneer Valley
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Top-rated condo rentals in Pioneer Valley
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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!

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.

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

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.

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!

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.

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

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.

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.

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.

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.

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.
Popular amenities for Pioneer Valley condo rentals
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Cozy and luxury room.

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2BR condo w/ golf course views, balcony, fireplace
Condo rentals with a pool

Jiminy Peak Apartment

THE SLOPE slope-view Country Inn 1BR w/heated pool

Vacation Village in the Berkshires-1 BD

Peaceful 1BR Condo with Pond View

Vacation Village in Berkshires 12/28/25-1/4/26

Ski-in/Ski-Out on Jiminy Peak

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- Condo rentals Massachusetts
- Condo rentals United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- University of Connecticut
- Dcu Center
- Ski Sundown
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Smith College
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Hancock Shaker Village
- Connecticut Convention Center
- Mount Holyoke College





