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Compare 248 Vacation Homes in Brainard with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 850 total
includes taxes & fees
13 Mar - 14 Mar
Berkshire Village Carriage House - Super Private!!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,243
SAR 3,981 total
includes taxes & fees
18 Mar - 19 Mar
Hancock Village Inn at Jiminy Peak

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (119)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (108)
"Great stay. Beautiful home. Warm and inviting "
4 Bdrm Modern Victorian with Tree House and playground

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (67)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is SAR 544
SAR 1,330 total
includes taxes & fees
13 Mar - 14 Mar
Near Tanglewood: Historic Summer Retreat

Comfortable Berkshires retreat on mtn resort, SISO

The price is SAR 604
SAR 1,818 total
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views

Spacious 5-bed house centralized within hour of skiing, Race track & Lake George

10.0 out of 10, Exceptional, (1)
"Spacious home for my family to gather during a death in our family. Great communication with host, house was very well equipped with everything you could need. Thank you."
Spacious 5-bed house centralized within hour of skiing, Race track & Lake George

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

10.0 out of 10, Exceptional, (9)
"Our family of six stayed at Lee Manor during the Christmas holidays. The house was a lovely older home with modern amenities. It was very well stocked with all the needs of home. The house was spacious and the beds were very comfortable. We enjoyed the back sitting area with the stove heater for watching movies, playing games in the front room, and gathering in the kitchen for snacking. We had great communication with the owners and the Check-in and Check-out process was flawless. It was a...
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (139)
"We had a wonderful trip, the kitchen is fully stocked with tons of kitchen tools, 2 slow cookers, etc! Cooking basics were available, soaps, dishwasher pods etc! The rooms were great! The playroom was amazing for all the kids! We had a wonderful time and will be back! "
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"
Dancing Horse Lodge

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (20)
"Rainbow Haven is quaint, quiet, private, clean, well-appointed and perfectly located. We were 2 families with kids ranging from (8-10) and a 1yr old Rhodesian Ridgeback - we thoroughly enjoyed staying at the Sharpe’s place. Plenty of activities for everyone to enjoy, comfortable bedding and gracious common-spaces. We had lunch in Lenox at Zinc bistro (yum). We will definitely be returning. . "
Secluded Family Home in Serene Stockbridge Woods

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (4)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
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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Other property types in Brainard

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is SAR 446
SAR 527 total
includes taxes & fees
16 Mar - 17 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is SAR 559
SAR 613 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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.