Holiday accommodation with a balcony in Richmond

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Top-rated Holiday Accommodation with Outdoor Verandahs in Richmond

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Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

30 Sept – 7 Oct

$1,746 AUD total

Guest favourite

Home in Canaan

5.0 out of 5 average rating, 18 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

17 – 24 Mar

$3,343 AUD total

Guest favourite

Home in Canaan

5.0 out of 5 average rating, 15 reviews

Private Retreat! Hot Tub, Pool Table & Movie Room

Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berkshires/Hudson Valley home has to offer. From skiing to Tanglewood, local farms to wineries, you’re close to it all! In summer, you have access to Queechy Lake’s private beach, included with your stay! Or if you’re more of a homebody, relax in the hot tub lakeside while watching the otters, curl up by the wood-burning stove, or play a game of pool. You’ll never want to leave!

5 – 12 Sept

$3,710 AUD total

Superhost

Apartment in Pittsfield

4.86 out of 5 average rating, 42 reviews

The Sunset Sanctuary - King Bed with Kitchen

Welcome to our cozy 1-bedroom apartment with a charming front porch and a private entrance with ample parking! Nestled in a peaceful neighborhood, this inviting retreat is the perfect place for a relaxing getaway or a romantic escape. The house is located just opposite of the Cumberland gas station where you can get breakfast, snacks, drinks or coffee along with any essentials. It’s only 3 mins drive from the Berkshire Medical Center and 20 mins drive from Tanglewood.

18 – 25 Sept

$848 AUD total

Guest favourite

Apartment in New Lebanon

5.0 out of 5 average rating, 9 reviews

Folk Art Studio: 1-bedroom near the Berkshires

Peaceful and characterful 1-bedroom apartment that's part of a Victorian house from 1830. We call it the Folk Art Studio because it has a primitive, imperfect, colorful feel, but is also very comfortable and quite modern. Fully stocked kitchen, bath with tub, washer-dryer, work space, good wifi, lovely living room, round dining table, and private garden access. It's on a quiet country road that offers historic houses and fantastic access to the Berkshires.

3 – 10 Apr

$1,345 AUD total

Guest favourite

Cottage in Malden Bridge

5.0 out of 5 average rating, 19 reviews

Cozy, charming cottage by the creek

Take it easy at this unique and tranquil getaway across from the Kinderhook Creek just outside of Malden Bridge, NY. Great for walkers, bike-riders, fishermen and fisherwomen, and lovers of natural beauty. Great fishing and swimming holes nearby. Well-supplied kitchen, washer and dryer, and lightning fast internet. Well-mannered dogs considered. Fenced in yard. I prefer no cats, as so many people are allergic (not me—I love cats), but exceptions can be made.

5 – 12 June

$1,477 AUD total

Guest favourite

Home in Richmond

5.0 out of 5 average rating, 27 reviews

Berkshire Cottage Retreat in Idyllic Setting

Discover tranquility at this charming 2-bed, 1-bath guest cottage in Richmond, MA, nestled in the Berkshires. A haven for outdoor enthusiasts, enjoy hiking, biking, kayaking, and winery visits. In summer, indulge in Richmond Pond's allure, while winter brings skiing at nearby Bousquet Mountain. Explore Tanglewood, Clark Museum, and more for a well-rounded retreat. Your ideal escape awaits, promising a perfect blend of nature and cultural delights!

18 – 25 Mar

$3,857 AUD total

Guest favourite

Apartment in Hudson

4.95 out of 5 average rating, 100 reviews

Restored 19th century farm house apartment

Brought back from the original bnb boarding days of the 19th century is our 1 bedroom top floor apartment located on a peaceful country road 15 minutes from downtown Hudson or Red Hook. You can still see the original numbers of the old boarding house on the doors! The house is surrounded by 12 acres of fields and forest that we welcome you to explore. It’s a small homestead with animals, a geo dome greenhouse and garden. Hope you enjoy!

26 Mar – 2 Apr

$1,147 AUD total

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 272 reviews

Sugar Shack - 300 square feet of pure sweetness.

A very PRIVATE OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, theater. A blissful & sweet retreat only 2.5 hrs from NYC & Boston. This custom space (tiny home+hot tub+she-shed) provides the utmost privacy and is thoughtfully designed with indulgence in mind. Hike, explore town, soak in your private hot tub, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

28 July – 4 Aug

$2,843 AUD total

Guest favourite

Condo in Hudson

4.94 out of 5 average rating, 141 reviews

Harmony Valley Home, bright & inviting 2-BR escape

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries breweries Musuems Hiking trails Empire State Rail Trail Conservation Areas

21 – 28 Oct

$1,578 AUD total

Guest favourite

Guesthouse in Lenox

5.0 out of 5 average rating, 11 reviews

Guest House at Stonover Estate

Located on historic estate grounds, this is an aesthetically pleasing and private getaway for adults and couples. The town of Lenox hosts multiple 5-star restaurants, and the property is an 10 minute walk to town. It is 1 mile from Tanglewood, 1 mile to Shakespear & Co., and 14 miles to Jacob’s Pillow. If you like the outdoors, it is a half mile to Kennedy Park for hiking or biking.

6 – 13 Nov

$2,882 AUD total

Guest favourite

Home in Richmond

4.92 out of 5 average rating, 12 reviews

Berkshire Beauty-Full Home

Relax with the whole family in this newly updated Richmond ranch. Fully stocked home with 2 car attached garage & beautiful outdoor space in a bucolic, central location. Right up the road from Bartletts Apple Orchard and Richmond Pond. Minutes away from Tanglewood, Bosquet and other Berkshire attractions. Let our clean, well appointed home be your own home away from home!

12 – 19 Dec

$3,907 AUD total