Places to stay near Mount Tom State Reservation

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location​ with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Spacious Charming New England Cape

Beautiful, relaxing area across from woods. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails in winter too! Close to Skiing, MGM Casino, tons of golf courses, beaches. Need a few more rooms? Ask about our 3br house next door which may be available.

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

Cheerful 2 Bedroom Home at Highland Lake

Welcome to the Uncorked Cottage, a fun and relaxing space for you and your family to retreat to. Comfort meets style in this updated home with a cozy remote gas fireplace, 55” smart TV and high speed WiFi. The kitchen is fully equipped cook up your favorite recipes. Located across the street from Highland lake and walking distance to Resha Beach. Just minutes from downtown where you’ll find restaurants and activities for all. Just a short drive to ski mountains.

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.

Quiet getaway in the Berkshires

Very nice quite place Two floors must climb stairs 3 bedrooms very large master Fully equipped kitchen Two full baths and laundry area Deck off the kitchen with fire pit in the back yard Lots of hiking and skiing in and around the area or stay and relax Carm’s diner for a great Breakfast Chester Common Table for dinner or The Blue Note Cafe for Pizza and a drink or Call for some takeout and a convenient store for anything you forgot

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage.

Berkshires Cabin in Woods with Mountain Views

A private hilltop Berkshires cedar cabin nestled amongst beautiful woodlands. Unwind with breathtaking mountain views from charming double balconies. Gather on the serene screened-in porch for meals. Get cozy with s’mores by the fire at night with an unobstructed view of the stars. Head to nearby Great Barrington for dinner. This is a perfect getaway to relax in peace and quiet and connect with nature, family and friends.