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Compare 293 Vacation Homes in Brainard with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (243)
"Celebrate 34 anniversary great place. Better than a hotel. Love the place would stay again. Couldn’t figure out how to use Apple TV to watch Netflix. Just need a couple steak knives if you do take out or cook in. Had a great time. Thanks Ed"
The price is AED 551
AED 841 total
includes taxes & fees
3 May - 4 May
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 AED 2,017
AED 3,801 total
includes taxes & fees
28 Apr - 29 Apr
Hancock Village Inn at Jiminy Peak

Romantic Villa

10.0 out of 10, Exceptional, (21)
"Great place."
Romantic Villa

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Oasis Just You, The Lake & The View!

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

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"Bassinova-on-Hudson is a gorgeous and well-kept property, and Jean and her staff are very responsive and welcoming. The home features everything a group could want in a secluded getaway - a gated, private entrance, 5 bedrooms, a game room with billiards table, a home theater, sonos throughout the house, a steam shower, and an enormous kitchen and outdoor grill.When I arrived with my wife and 19 month old, Kat gave us a quick tour of the house and explained how everything worked, and the basic...
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

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

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (110)
"Our family stayed there, and we had room to entertain extended family. Nice quiet neighborhood. Clean and spacious with a large yard. Conveniently located near grocery store and restaurants. We will stay there again!"
4 Bdrm Modern Victorian with Tree House and playground

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"We had a great stay, thank you! Everything was great as all accommodations were met and other than getting food from the local nearby grocery store and our own personal things, nothing more was needed. Everything went so smoothly, other than our two dogs being home sick and whining at times, which ended up entailing a 7 hour round trip back home to leave them there with a sitter as we felt it was too much for our little fur babies to endure being in a strange place without us and better to...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

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

10.0 out of 10, Exceptional, (121)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"
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

9.6 out of 10, Exceptional, (41)
"This is a great little house in Pittsfield. Location was perfect for us, as it's just a couple of miles from our son's apartment. It's a beautiful farm, tucked away on a back road. It seems "rural" when you're at the house, but it's actually right near everything you could possibly need. The owners were great with communication and very accommodating. We hope to be back, and it's great to know that the house has enough room for our other kids to join if they want to. "
Dancing Horse Lodge

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

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (34)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
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, (1799)
"What a beautiful place. Could not be more beautiful and we are so satisfied. We will be back!"
The price is AED 403
AED 482 total
includes taxes & fees
4 May - 5 May
Vacation Village in the Berkshires

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Lovely, and quiet, with water nearby. Everything was nice and worked, and owner responded to communication quickly. Will visit again! "
The price is AED 477
AED 515 total
includes taxes & fees
11 May - 12 May
Micosta Leisure Inn

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
28 Apr - 29 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.