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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 551
AED 833 total
includes taxes & fees
9 Feb - 10 Feb
Berkshire Village Carriage House - Super Private!!

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

10.0 out of 10, Exceptional, (22)
"This property was excellent for our family of 13 plus two dogs. We loved having a great t.v. room where kids could play and a second living area for the adults. Well equipped with games and puzzles. Great location for bucolic road walks. Summer would be great."
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (36)
"Our family recently stayed at this incredible vacation rental to celebrate a grandparent’s birthday, and it was truly the perfect setting for a special gathering. With 6 adults and 6 children under the age of 7, finding a place that could comfortably accommodate all of us was no small task—but this property exceeded every expectation. The location was ideal, with easy accessibility for family members traveling from different parts of the country and a manageable drive from Hartford airport....
Beautiful Berkshire Farm House on 160+ Acres

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (39)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "
Hudson Valley and The Berkshires getaway

Amore Estate - beautiful room with many places to explore and relax in.

9.2 out of 10, Wonderful, (20)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views

2 bedroom town house with game room

6.4 out of 10, (13)
"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."
The price is AED 331
AED 551 total
includes taxes & fees
11 Jan - 12 Jan
2 bedroom town house with game room

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (18)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is AED 441
AED 1,185 total
includes taxes & fees
4 Feb - 5 Feb
Near Tanglewood: Historic Summer Retreat

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"It was gorgeous, and we had a wonderful cozy time. "
Hearts Desire is a furnished whole house in a small, colorful garden center.

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (21)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 1,153
AED 2,205 total
includes taxes & fees
12 Jan - 13 Jan
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (19)
"Amazing and lovely"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (89)
"Chip and Kim are exceptional hosts, and we enjoy coming to this property every Thanksgiving to gather as a family. It meets all of our needs, and we love it!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Spacious Historic Home in the Berkshires!

9.8 out of 10, Exceptional, (6)
"This lovely home was ideal for my family of 8: my children and their spouses, two grandchildren, myself and two pups. The beds were plentiful and comfortable. The house, while old, was newly remodeled, adding modern appliances to the charm of the original building. Very bright and spacious in a quiet neighborhood, convenient to Lenox, Tanglewood, and other special towns. I highly recommend this home to anyone looking for a pleasant retreat. We loved every minute!"
Spacious Historic Home in the Berkshires!

Loft Style Cabin In West Stockbridge, Book Now!

10.0 out of 10, Exceptional, (2)
"Great place, all amenities are well kept and the atmosphere of the interior is very cozy. We thoroughly enjoyed our weekend here and would definitely stay again! "
Loft Style Cabin In West Stockbridge, Book Now!

Best of the Berkshires & Hudson Valley

10.0 out of 10, Exceptional, (3)
"My wife and I had a wonderful stay at Mai's house in the Berkshires. Set back on a dirt road overlooking beautiful fields and woods, the house is a great place to relax. A 18th century farmhouse stylishly updated provides a great location to enjoy all the natural and cultural treats the Berkshires has to offer. Mai is a warm friendly host and promptly responds to any problems or issues that arise. We highly recommend Knoll Woods."
Best of the Berkshires & Hudson Valley
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, (1752)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is AED 689
AED 792 total
includes taxes & fees
14 Jan - 15 Jan
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AED 694
AED 762 total
includes taxes & fees
14 Jan - 15 Jan
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (92)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is AED 433
AED 468 total
includes taxes & fees
6 Feb - 7 Feb
Micosta Leisure Inn
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.