Bed and breakfast holiday rentals in Lenox

Rocky Ledges

Our house was a historic cottage, built in the 1880s. We built a new house around the cottage. We are Artists and our guest bedrooms are in a sense galleries. Guests have the entire second floor, 2 bedrooms, perfect for couples who are traveling together & families with teenagers. The back is the private entrance to the stairs. We live on a quiet and pleasant dead end street. The views of the Catskills & gardens are awesome. Located near Hunter Mountain Festivals, Woodstock & Katterskill Falls.

Find your escape at The Coldbrook House, Mt Snow

A beautifully-secluded modern ski home near Mt Snow with 500 feet of private access to the Cold Brook. Exceptionally furnished with custom wood flooring and stone fireplace, Subzero & Wolf appliances, walk-in shower with custom river rock flooring, pool table, shuffleboard, and 7-person hot tub. 10 min to Mount Snow, 30 to Stratton. 5 min to downtown Wilmington and Herriman Reservoir. Perfect for 3-4 families or couples trips. Come enjoy the beauty of Southern Vermont at The Coldbrook House!

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

Upstate Daydreamers Guest Suite

A spacious 3-room private suite for 1-2 guests. The vibe is cozy, quiet, safe, peaceful, comfy — unwind and make yourself at home! Explore our 14 acres of lush forest and creeks, take a bubble bath in the clawfoot tub, soak in the jacuzzi, play mini pool, and collect fresh organic eggs from the chickens. Free on-site parking, excellent cell reception & wifi. Please note, we're no longer serving breakfast - visit our restaurant Ace of Cups (inside Tubby’s) & receive free dumplings instead!

Palazzo Hudson: Luxury Home w/Pool, Hot tub, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Mountain home with views

Spacious home with sunset-facing views, surrounded by woods, creek, wildlife. Listed as 2BR (queen & king BRs) but has 2 addt'l rooms with beds - twins & bunk beds (see photos). Rental includes the whole house - sleeps 10. 5 mi to Phoenicia, 10 mi to Woodstock. Hiking, restaurants, activities nearby. Private, peaceful, and woodsy, with easy access to town. Wifi. Fire pit. Hottub. For long term rentals for this property, go to airbnb.com /rooms/51687679 (del the space after com)

Welcome to the "Red Bridge Cottage"

Welcome to "The Red Bridge Cottage" a 2 minute walk to the Kinderhook Creek (a Hudson River estuary) with the best trout fishing! This newly renovated cottage has all new kitchen appliances including a new washer and dryer. Comforts include: Central AC & whirlpool tub! Locally and only 3 miles away is the Empire State Bike Trail - a 750 mile trail connecting urban centers, village main streets and rural communities with informational boards on the interesting local wildlife.

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Need a Getaway??

This ideal location is perfect for all seasons , visiting family, college visits, extended stays for business travelers and lots of outdoor recreation. Located about 20 minutes from Saratoga’s city line. This beautiful, quiet and spacious apartment on the 2nd floor overlooks several acres of land. Also, a perfect halfway point between Canada and New York City. We offer complimentary coffee, eggs & pancake mix to cook in the full size kitchen. Pool is heated!

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).