Vacation rentals in Alford

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Top-rated vacation rentals in Alford

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Top guest favorite

Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

4.92 out of 5 average rating, 147 reviews

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

An aerial view captures the serene landscape surrounding the home, showcasing a mix of trees transitioning into autumn colors. The house is situated on a green patch of land, with a winding path leading towards it, surrounded by the natural beauty of the countryside.

Home in Town of Hillsdale

Gorgeous Mountain Views Retreat: Family & Nature

Escape to Meadow View Manor, a 4BR modern-rustic Hillsdale retreat set on 6 private mountainside acres near the Berkshires. Wake to fog lifting over the hills, then gather around the brick fireplace, cook in the remodeled kitchen, play ping-pong, or enjoy the expansive deck and fire pit. Sleeps 8 and welcomes dogs. With no nearby neighbors, hear only birds and wind. Just 2 hrs from Manhattan, 10 min to Catamount, 15 min to golf, dining and live music, and 30 min to Hudson or Great Barrington.

4.98 out of 5 average rating, 83 reviews

Guest favorite

A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.

Apartment in Great Barrington

King Bed | Patio | 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

4.91 out of 5 average rating, 186 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 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

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

Cottage in Great Barrington

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

4.94 out of 5 average rating, 355 reviews