For families seeking a calm refuge from New York City or Boston, these Berkshire vacation rentals are the answer.
The Berkshires embodies all the best that New England has to offer for a year-round getaway. Spectacular hikes and drives, a local farming and food scene, fall foliage, water and mountain sports, and four centuries of iconic American history and architecture to keep any family busy.
Popular towns include Lenox, Stockbridge, Great Barrington, Williamstown, Massachusetts and Chatham, New York for their cultural and leisure offerings.
The Berkshires offers some advantages of history, culture, and dining that the rest of New England can’t fully boast. Its proximity to New York City has given the Berkshires an edge with a food scene, modern art, and all the essentials that even a discerning Brooklynite might need.
Fear not, as we at Luxe Recess have scoured through hundreds of vacation homes to show you the very best for gathering the whole family to celebrate the holidays or just a change of scenery.
You will not find matching pairs of burgundy La-Z-Boys in these homes. These have been selected for only the best Berkshire vacation home experience including design and amenities. Nearly all have a 5-star rating from prior renters, and all welcome children.
Read our complete guide to the Berkshires,
town by town
Berkshires NY Home Rentals
1) Bellavista Country Estate
Old Chatham, NY
- House: 12,000 sq. ft.
- Sleeps: 16
- Bedrooms: 7
- Bathrooms: 5
- Min Stay: 2 nights
- Pool: Outdoor
- Kids’ Amenities: Playroom, playground, arcade
- Style: Shabby Chic
The Bellavista Country Estate has long served as a destination wedding site in addition to offering shorter stays for families.
The stately Georgian home has seven bedrooms and sleeps sixteen people. Its real estate, in total, spans sixty acres, with an outdoor pool, pond, arcade room, private gym, and hiking trails. Kids will love that there’s a playground and playroom. Those traveling in the winter can visit area ski resorts, or, indoor tennis courts one-half mile away. While the bones of this Georgian estate are beautiful, its interior is simple and a bit on the shabby-chic side.
2) Sunny Pond
Austerlitz, NY
- House: 7,500 sq. ft.
- Sleeps: 16
- Bedrooms: 6
- Bathrooms: 4
- Half Baths: 1
- Min Stay: 1 night
- Pool: Private pond on property for swimming and pedal boat
- Children’s Amenities: Playground, ping pong table, game room / play room with toys and games, media room
- Style: Casual
This newly renovated Georgian Colonial home sits on forty acres with a private pond.
Perks include a very spacious chef’s kitchen, several fireplaces, a secluded office, a children’s room with bunk beds and a twin beds trundle. The finished basement includes a children’s playroom and well-stocked gym.
There’s an additional guest apartment on site to sleep six more guests with its own small kitchen and living room.
3) Two Ponds Compound
Chatham, NY
- Sleeps: 10
- Bedrooms: 5
- Bathrooms: 4
- Half Baths: 2
- Min Stay: 4 nights
- Pool: Outdoor
- Kids’ Amenities: Not ideal for young kids
- Style: Clean and modern
Maybe you want to escape city life to a modern compound designed by an I.M. Pei disciple?
Arthur Hadley, a journalist and author known for his military critiques, purchased the building from architect Parker Bloser in 1988.
Bedrooms are spread between two buildings for families with adult children or additional space needed for remote work. The detached building has two queen bedrooms with a shared bath; there are three bedrooms in the main house.
This rental is the perfect choice for those whose design standards remain high particularly regarding upscale interiors.
For those weary of leaving the comforts of home and their own well-appointed kitchens, the Two Ponds kitchen includes a Liebherr fridge, Jenn-Aire double oven, Gaggenau stovetop & two dishwashers.
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Berkshire Rentals In Western Massachusetts
4) Dreamy Southern Berkshire Estate
South Egremont, MA
- House: 6,000 sq. ft.
- Sleeps: 14
- Bedrooms: 5
- Bathrooms: 6
- Half Baths: 1
- Min Stay: 7 nights
- Pool: Outdoor
- Kids’ Amenities: Playground, apple orchard, vegetable garden that guests can harvest and eat, piano
- Style: Ready for a magazine spread
This spectacular home in the southern Berkshires is the most luxuriously appointed of all Berkshire vacation rentals, and its price reflects it. This immaculate home’s landscaping and interior design are for the most discriminating of guests.
It’s the ultimate choice for large groups and multi-generational travel. There’s a gourmet kitchen with sub-zero and Wolf appliances and a dining room that can seat fourteeen. Depending on the season, guests are allowed to harvest what’s growing in the organic garden for themselves.
This estate includes a security system. Extra perks include a Peloton bike in the home gym and a grand piano in the main room.
Read our complete guide on
where to eat in the Berkshires
5) The Hill in Great Barrington
Great Barrington, MA
- House: 5,000 sq. ft.
- Sleeps: 12
- Bedrooms: 5
- Bathrooms: 4
- Half Baths: 1
- Min Stay: 60 nights
- Pool: Outdoor patio hot tub, swimming within a 10 minute walk
- Children’s Amenities: Playground, ping pong, children’s books and movies, Sony PlayStation, toys
- Style: Casual
A spacious in-town location with Great Barrington’s shops and restaurants only fifteen minutes on foot. Lake Mansfield with a swimming beach is within walking distance (approx. seven minutes away).
The house was built in 1910 has been meticulously restored with new baths, home audio, and a gourmet chef’s kitchen.
There’s a deck with a 9-person hot tub, a ping pong table, and a playground in warmer months to enjoy the large lawn and blueberry bushes.
6) The Taggert House of Stockbridge
Stockbridge, MA
- House: 9000 sq. ft.
- Sleeps: 12
- Bedrooms: 6
- Bathrooms: 6
- Half Baths: 2
- Min Stay: 3 nights
- Pool: No, riverfront property for wading and fishing
- Children’s Amenities: Crib and Pack N’ Play, children’s themed bedroom with two beds
- Style: Traditional with antiques
Steps from the Red Lion Inn and the village of Stockbridge, the Taggert House is a meticulously-restored Berkshire cottage that was recently added to the National Register of Historic Places. Downtown Stockbridge has adorable shops and restaurants just minutes by foot; the highly-regarded Norman Rockwell Museum is only a five-minute drive.
This home and its interiors are elegant but not fussy. With both a billiards room and a conservatory along with a library, families must bring along their Clue board game from home, and maybe figure out how to create a life sized version of the game throughout the house. Constructed in 1850, the Taggart House combines fine nineteenth-century architecture with comfort and up-to-date amenities (cable, internet, modern air conditioning, outdoor gas grill).
A ballroom can be rented separately but isn’t included in standard rental listings.
7) Views of Undermountain Road
Lenox, MA
- Chalet: 6,000 sq. ft.
- Sleeps: 14
- Bedrooms: 5
- Bathrooms: 5
- Half Baths: 1
- Min Stay: 3 nights
- Pool: No
- Children’s Amenities: Ping Pong, Pool Table, Media Room, Crib
- Style: Contemporary
As a Berkshire visitor for thirty years, Undermountain Road in Lenox is my favorite drive in all of the Berkshires. This Berkshire vacation home is near the main entrance to Tanglewood.
This modern, shingled home showcases its mountain views from several windows. There’s a large deck and screened-in porch to relax while looking at the views.
The owners have grown children now, so there is more of an adult feel to the space. The heart of Lenox is a three minute drive with its downtown restaurants, shopping and an excellent public library.
8) A House To Unplug on a Private Lake
Lee, MA
- Sleeps: 10
- Bedrooms: 4
- Bathrooms: 3
- Min Stay: 3 nights
- Pool: Private lake, hot tub on deck
- Children’s Amenities: Ping Pong table
After driving a quarter of a mile down this remote road you’ll reach this home situated on thirty-six (very) private acres. This three-bedroom home isn’t for large gatherings, but it’s perfect for a family to get away from it all and feel restored by its spectacular views and its private lake. This is one of the more affordable Berkshire vacation homes on our list.
There’s a porch, fire pit, and hot tub for families to spend the night looking up at the sky and wiping melted chocolate off their chins.
This is more of an “unplugged vacation” where the owner admits that the internet connection is slow. Its open floor plan is ideal for families to gather and recharge without screens.
The location of this home is truly advantageous because, despite its remote setting, it is centrally located to everything in Lenox, Stockbridge, and Great Barrington, as well as the Mass Pike.
Read our complete guide on what to do in
the Berkshires for families.
Photos courtesy of VRBO.com.
Your links do not take me to the homes listed!! Pls fix or send info how to reserve.
The home rental market is dynamically changing since COVID. Though this article is only a few months old, if the listing is no longer active the link will take you to a search page. The home links work if the home is still for rent.