Vacation rentals in Alford

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Top-rated vacation rentals in Alford

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Top guest favorite

Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 110 reviews

Guest favorite

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

4.95 out of 5 average rating, 191 reviews

Top guest favorite

A bright sitting area features a blue sofa adorned with decorative pillows, flanked by two wicker chairs. A wooden dining table is positioned by a large window, providing natural light. Shelves display various decorative items, enhancing the studio's inviting ambiance.

Loft in Great Barrington

Studio in Bucolic Berkshire Setting

The 600 Sq. Ft Studio with skylights has a sitting area with sofa-bed, flat screen TV/DVD, sleep area with queen-size bed, dining area, fully equipped kitchen and full bath with shower. Views overlook a 30 acre farm (south) and mountains (east). The studio is in a separate building with a private entrance. The 4 acre property includes perennial and vegetable gardens, an orchard and walking paths. The studio is easily accessible to biking, hiking, swimming, and numerous cultural attractions.

4.97 out of 5 average rating, 140 reviews

Guest favorite

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

4.96 out of 5 average rating, 114 reviews

Top guest favorite

A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.

Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

4.98 out of 5 average rating, 253 reviews

Guest favorite

Guesthouse in Great Barrington

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.95 out of 5 average rating, 177 reviews

Top guest favorite

Home in Great Barrington

Beautiful House in the Woods: Huge Yard, Hot Tub

Experience the charm of country living year-round on 4+ acres of peaceful land, tucked away on a private lane just minutes from Downtown Great Barrington and Tanglewood. This inviting home offers seamless indoor-outdoor living with abundant natural light, a spacious 1,000+ square foot deck, expansive yard, vibrant gardens, and a relaxing outdoor hot tub. Perfect for families, groups of friends, and even your well-behaved pup, this Berkshires retreat is a one-of-a-kind getaway.

5.0 out of 5 average rating, 27 reviews

Top guest favorite

A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.

Bungalow in Egremont

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

4.99 out of 5 average rating, 143 reviews

Top guest favorite

A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.

Home in Great Barrington

Seekonk Hill

Great Barrington countryside is waiting for you at this 2-bedroom house, nestled in a serene setting surrounded by conservation woodland and farm pasture. Walk down the winding driveway and find yourself one of the southern Berkshires’ finest walking and cycling routes. The property’s perennial gardens and maintained apple orchard offer brilliant flowers in the spring and summer and apple picking and foliage in the fall. Come enjoy each season's unique brilliance.

4.98 out of 5 average rating, 48 reviews

Top guest favorite

Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

4.97 out of 5 average rating, 185 reviews

Top guest favorite

Home in Great Barrington

RENOVATED BERKSHIRE COUNTRY CASTLE

New 3 BR rustic-yet-elegantly modern 2300 sq ft country castle set on on 3.5 secluded acres in Manor Lane, a private compound off Hurlburt Road in Great Barrington, MA. This property offers the perfect balance of peaceful seclusion and year-round convenience. We call it the GreatBarringtonCastle House, but it's much more farmhouse/luxury villa. Take the time to read the full description below -- you won't be disappointed.

4.97 out of 5 average rating, 58 reviews

Top guest favorite

The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.

Home in Great Barrington

Berkshires Black Abbey

Relax in a luxurious 4-person cedar sauna at the Berkshires Black Abbey, an 1862 church turned stunning 3-bed, 3-bath home in Mill River Village, MA. This 4,000 sq. ft. retreat blends original stained glass and vintage charm with modern comforts like heated floors, rainfall showers, a game loft with a speakeasy bar. Spacious deck, full kitchen, and room for up to 10 people

5.0 out of 5 average rating, 47 reviews