Ski-in/Ski-out vacation rentals in Massachusetts

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

Value · Family · Pets

Lakefront Oasis at Lake Wyola

Come enjoy our fully appointed lakefront home on Lake Wyola. With your own waterfront access and 180 degree views from the living, kitchen, dining, and master bedrooms, this comfortable getaway will not disappoint. We are just 20 min from Amherst and 35 min to Northampton with easy access to all of the five colleges. Enjoy morning coffee with flawless views from our wraparound deck. Miles of hiking trails just steps away. Three bedrooms with fully equipped kitchen and open concept living/dining.

Location · Family · Decor

Spacious 1-Bed Apt. in Peaceful Weymouth W/Balcony

Spacious and sunlit 1-bedroom apartment in a peaceful Weymouth neighborhood, featuring a private balcony and relaxing views.Perfect urban retreat for relaxing or working from home, blending quiet natural beauty with excellent proximity to local seaside parks and easy Boston commuting.Open-concept layout featuring oversized windows that flood the apartment with natural light & connect directly to your private balcony offering quiet, peaceful views, perfect for morning coffee or evening unwinding.

Value · Location · Kitchen

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

Family · Value · Walkability

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Family · Location · Hospitality

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Location · Value · Sleep quality

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

Family · Location · Kitchen

Stump Sprouts Lodge

Perfect location for a get together with family and friends! This is a one-of-a-kind guest lodge atop a high meadow with magnificent views. 400 acres. Right from our door, you'll find 15 miles of groomed x-c skiing, fat biking, and snowshoe trails in winter, hiking & mountain biking trails in the summer. Sauna, large living rooms. Commercial range in kitchen, large dining room. 10 minutes from Berkshire East, whitewater adventures, canopy tours, mountain biking and more.

Value · Family · Outdoor spaces

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

Location · Value · Layout

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Value · Family · Checkout

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Value · Location · Accuracy

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.

Location · Value · Condition