Apartment holiday rentals in Pioneer Valley

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Top-rated apartment rentals in Pioneer Valley

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Superhost
Apartment 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

Top guest favourite
The condo building is surrounded by a thick blanket of snow, with multiple units visible. The exterior features a green color and large windows. Snow collects on rooftops and the ground, creating a serene winter scene with trees in the background.
Apartment in Dover
4.94 out of 5 average rating, 158 reviews

3 Story Condo - 5 Minutes to Mount Snow!

Charming Dover Green condo just minutes from Mount Snow Ski Resort & Lake Whitingham. This well kept 2 bedroom, 2 bathroom, plus loft bedroom features open concept living, dining, vaulted ceilings, natural woodwork, 65" TV, and a wood burning fireplace. With easy access to Mount Snow, the village of Wilmington, nearby lakes, hiking, and biking, there is so much to do for tremendous year round enjoyment. There is nearby access walkable from the unit to the public MOOver shuttle to get around town

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.
Apartment 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.
Apartment 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!

Top guest favourite
Apartment in Dover
5 out of 5 average rating, 12 reviews

Fully Renovated 3 BR Condo - 0.8 mi to Mt. Snow

Fully renovated for 2026, bright and stylish 3BR/2.5BA ski condo. Located just 0.8 miles from Mount Snow. On the free Moover shuttle line Features: - Spacious living area with all-new flooring, furniture, fireplace - New kitchen - 2 full bath, all-new with walk-in showers. 1 bathroom with a sauna - Basement rec room with basketball, Nintendo switch 1+2 docking stations, 4-player arcade cabinet with 1000+ games - Locked storage for skis/boards BR 1: King bed BR 2: Queen bed BR 3: 4 twin beds

Guest favourite
A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.
Apartment in Dover
4.91 out of 5 average rating, 67 reviews

Ski Condo 5 Min from Mt Snow

Your family will be close to everything when you stay at this centrally-located condo. Cozy and clean, only 5 min to Mt Snow Resort for skiing/boarding in winter or golf & mtn biking in spring, summer, & fall. 2 minute walk to Snow Republic Brewery. Close to the towns of Dover & Wilmington for shops, restaurants, and country charm. Minutes from hiking, biking, and golf for outdoor enthusiasts, only ten minutes from the tranquil Lake Raponda. Notify if bringing pets. 2 car maximum or inquire

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.
Apartment 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.
Apartment 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
Apartment 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 favourite
Apartment in Dover
5 out of 5 average rating, 16 reviews

Walk to Food/Entertainment, 5 Min Drive to Mt Snow

Enjoy the natural beauty and charm of Vermont in this ground-level condo just 5 minutes from Mount Snow. Perfect for skiers, riders, and year-round explorers, this cozy space combines modern updates with rustic charm. - Walk to restaurants, bars, and an arcade - Grab the FREE shuttle to the base of Mt. Snow at the bottom of the driveway - Visit Horace Hill Recreation Area featuring MTB trails and an 18-hole Disc Golf Park

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.
Apartment 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.
Apartment 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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