Bed and breakfast vacation rentals in Lenox

Unique Converted Carriage House and Barn Compound

The house is set on five private acres surrounded by hundreds more and accessed by a long private gated driveway. Guests will have the experience of being on a secluded private estate, yet be just minutes to the center of the village- truly the best of both worlds! The House: This is a charming and rambling home that combines modern comforts with the texture and character of the 19th century. The ground floor of this three story house has a large open plan living/dining room with a fireplace and two doors out to the patio and grounds on one side, and the porch, gardens and guesthouse on the other. This space flows into a large open country kitchen, with a vintage garland stove, dishwasher and microwave, and has a powder room and laundry off of it as well as a door leading out to the patio. On the second floor is the large king sized master bedroom suite with its vaulted beamed ceilings, fireplace, private bathroom with a separate shower and bubble tub built for two and access to the grounds via a charming bridge. Also on this floor is a media room/library, two smaller sunny corner bedrooms and a third transitional room and a bathroom. The third floor has another king sized suite with vaulted ceilings and a large bathroom with tub and hand shower. There is Direct TV and a number of DVD players throughout the house. The guesthouse: Soaring cathedral ceilings , rustic exposed beams and loads of light set the tone for this dramatic and unique space. Each of the two bedroom suites, which occupy the top floor of the barn, has it's own bathroom with jacuzzi tub and skylight, decorative fireplace, seating area and french doors to a private deck with table and chairs. In the hallway between the two bedrooms there is a breakfast "mini bar" with a refrigerator, Keurig coffee machine, electric kettle and microwave oven and is stocked with coffees, teas, treats, hot cocoa and bottled water. The space is comfortably furnished with an eclectic mix of new and antique furniture, original artwork and prints with luxurious bedding and towels. This historic house and the barn once had a life as a true Bed & Breakfast and a few remnants of that period remain, namely the kitchy names for the guest rooms. The "Fox Den" looks out over gardens and main house and the "Huntsman's Hideaway" overlooks woods. There is air conditioning in both of the king suites in the main house as well as in both of the guesthouse suites. Guests will have full use of the house and grounds plus there is plenty of parking space. The grounds are spacious and varied and feature a koi pond, vegetable garden, cutting garden, herb garden, perennial beds, and a hammock with sculptures throughout to discover and room to stroll or run around I will personally greet guests whenever possible and give them the overview...after that you will be left to enjoy the privacy of the space and grounds. I will have books and suggestions for you if you want input on your stay. Rhinebeck sits at the crossroads of the historic Hudson Valley and there is a great deal to do. The town is full of charming shops, galleries, day spas and quality restaurants and hosts the finest farmers market in the county on Sundays. Guests will enjoy the house and grounds with plenty of parking space. The property is private, spacious and varied and features a koi pond, vegetable garden, cutting garden, herb garden, perennial beds, and a hammock with sculptures throughout to discover The Amtrak stops right in Rhinecliff Station if you want to take the train up but you really will need a car once you are here in order to thoroughly explore. Town is a 20 minute walk from the house or a quick bike ride if you bring one to tour the area on two wheels. Kayaks can be launched near Rhinecliff if you want to explore the mighty Hudson at water level which is great fun. The house is located just outside of the Village, and is set far from the road, accessed through a long gated private driveway. We share the driveway with our two neighbors and multitudes of deer, wild turkeys, foxes and other critters so drive with caution as you approach. Well behaved and house trained dogs are welcome but sadly we have a cat allergy in the house.

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

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.

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

Welcome to Palazzo Hudson! The only private vacation home in Hudson proper with a deluxe sauna, cedar hot tub, seasonal in-ground pool, chef's kitchen, & a pool-side lounge with a fireplace & art library! 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 & the Upper Depot District.

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.

Arnold Farmhouse (Italianate - private bath)

Private entrance to room with an attached bathroom. Enjoy the porch, garden, honey bees, the old farm/fields., situated on the bank of the Valatie Kill in the quaint hamlet. The AH Bike Trail is just around the corner, Larkin Hill, Kinderhook Creek & Hunt Club. We are 30 minutes from Albany or Hudson on excellent roads. Schodack Island is 15 min. Van Buren house is 15 also. Jiminy Peak Ski is a 30 min. It is a wonderful to get some real fresh air - good for couples, solo, and business.

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

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!

Stissing Lake House | Hudson Valley Lake Front

Picture yourself lying in the hammock or with a glass of wine on the porch. Jump into the lake for a refreshing swim, or sunbath on the dock. This property is all about being outdoors. Enjoy 11 blissful acres at the base of Stissing mountain. Swim, ski, hike the Appalachian trail. Located just 90 Miles From NYC in the Hudson Valley. 2022 renovated picturesque 125 yr old Victorian country estate is surrounded by a breathtaking lake & mountain view. Longterm rentals available

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!