Holiday rentals in The Berkshires

Vermont Lakefront Getaway "The Wild Loon"

This home was built in 2020 with the beautiful lake and mountain views in mind. The Wild Loon is what we decided to name our retreat because we are often visited by wild loons here on the lake. The Wild Loon has an open concept floor plan. Sleeping arrangements are upstairs and downstairs in the basement. The half bath, kitchen, living and dining room are all on the main floor. Parking is directly across the road and can fit 4 vehicles in the summer, spring and fall 3 vehicles during winter

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

River Cottage

Beautiful cottage in the Adirondack Mountains situated on over an acre of waterfront property with River access. Enjoy swimming, Kayaking and fishing on the Hudson River, all right from the backyard of the house. It has a great deck which overlooks the river with perfect views for enjoying sunset cocktails… Yard also has two fire-pits for night time fun and laughs. Cabin is close to skiing, snowmobiling trails. Perfect for a family getaway to make awesome memories. STAY, SPLASH, SMORES!!!!!

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

OnTheRiver/Adk decor, full kitchen, 2 bedrooms

This is the place for a wonderful, relaxing retreat. You’ll be pleasantly surprised when you open the door to your stay. It’s beautiful Adirondack decor is very welcoming and you will be very impressed with the sparkling cleanliness of this stay. Relax and enjoy all the comforts of home with WIFI, ATT and Verizon cell service. We have a full house generator, mini split for air conditioning, deck area, a grill, and an area with a fire pit all with the river and mountain view’s. Boat parking!

“Amazing Mtn & Ski Slope Views “

The highest breathtaking Mtn Views in Windham w ski slope and lake views. This amazing resort like atmosphere includes a 8 person hot tub w 5 acres of tranquility ,3 outdoor firepits , walking pathways through beautiful gardens with a ski lift chair and Adirondack chairs at fire pits also a Japanese style garden with serene lake & Mtn views as well as from every room in the home. Two fireplaces and a lg bar w game rm as well as 2 living rooms w tvs. A 4 min drive to town & 6 min to slopes.

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.