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Brainard Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Brainard vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,221 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is ￥13,696
￥18,835 total
includes taxes & fees
Nov 12 - Nov 13
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,774 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is ￥12,717
￥15,940 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

3. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥13,058
￥34,836 total
includes taxes & fees
Oct 22 - Oct 23
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is ￥11,080
￥32,568 total
includes taxes & fees
Oct 27 - Oct 28
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥13,454
￥35,651 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley
A wooden cabin with a porch, a door, and a window.

6. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is ￥17,807
￥26,794 total
includes taxes & fees
Oct 22 - Oct 23
Taborton Harvest Boulder Pines Cabin in the woods
A snow-covered outdoor area with a fire pit, tables, and chairs.

7. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥17,094
￥37,835 total
includes taxes & fees
Oct 22 - Oct 23
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is ￥17,094
￥37,835 total
includes taxes & fees
Oct 27 - Oct 28
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

9. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥35,455
￥87,713 total
includes taxes & fees
Oct 22 - Oct 23
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

10. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (9 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is ￥27,857
￥88,724 total
includes taxes & fees
Oct 22 - Oct 23
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

11. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was super clean, super comfortable, and so close to my family get together. I will definitely be back in September. Dillon was quick to respond and everything was exceptional."
United States
Sandra V.
The price is ￥19,152
￥44,866 total
includes taxes & fees
Oct 22 - Oct 23
2 Bed Berkshire Getaway @ Stephentown Hotel
A spacious kitchen with wooden cabinets, a large island, and a dining area with benches.

12. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (6 reviews)
"It was a great getaway "
United States
Chandra F.
The price is ￥17,807
￥26,794 total
includes taxes & fees
Oct 22 - Oct 23
Taborton Harvest Timber Trails Unique cabin experience
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

13. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (191 reviews)
"Great stay"
United States
George
The price is ￥15,624
￥17,500 total
includes taxes & fees
Nov 1 - Nov 2
Micosta Leisure Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

14. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥17,094
￥37,835 total
includes taxes & fees
Oct 22 - Oct 23
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

15. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥16,952
￥37,676 total
includes taxes & fees
Oct 22 - Oct 23
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Four people seated at a table with food and drinks, wearing winter sports helmets.

16. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is ￥17,094
￥37,835 total
includes taxes & fees
Oct 27 - Oct 28
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

17. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is ￥19,152
￥44,027 total
includes taxes & fees
Oct 25 - Oct 26
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A white two-story house with a porch, surrounded by trees and a hill.

18. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ￥31,181
￥73,638 total
includes taxes & fees
Nov 18 - Nov 19
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

19. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is ￥17,094
￥37,835 total
includes taxes & fees
Oct 27 - Oct 28
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A brick building with a wooden deck, a door, and a metal staircase.

20. Cozy Garden 2-Bed Full Amenities @ Downtown Albany

Cozy Garden 2-Bed Full Amenities @ Downtown Albany
Pastures
10.0 out of 10, Exceptional, (2 reviews)
"The garden apartment was very clean and the communication with the host was excellent. I liked that it was a 10 minute walk to my event at Capital Center. "
United States
Nina R.
The price is ￥12,227
￥27,162 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Garden 2-Bed Full Amenities @ Downtown Albany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Brainard Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Very nice. Not five-star nice, but great lodging in a stunningly beautiful setting. This was my second stay, and it was great. Room was clean and bed was very comfortable. The staff are extremely helpful. Breakfast was a little stodgy (toaster didn’t work and the selection was pretty standard motel fare). I’ll definitely return just because of the location. Eating breakfast while watching a variety of waterfowl landing on the lake is extremely peaceful."
Ronald 3-night trip
Posted 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Brainard

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Frequently asked questions

Can I find vacation rentals in Brainard?

Yes, we have vacation rentals close to top sights in Brainard, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Brainard has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: You might want to consider this vacation home rental near Brainard, which is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in Brainard?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Kinderhook Lake. In the larger area, you’ll find Queechy Lake and Hancock Shaker Village.

What’s a vacation rental in Brainard like?

Vacation rentals are private properties you can book for a couple of days or more in Brainard. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.