Brainard Vacation Rentals

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Nov 21 - Nov 23
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Jan 30 - Feb 1
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Feb 27 - Mar 1

Vacation Rentals in Brainard

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2124)
"Clean and great pool and hot tub facilities "
United States
Alyce
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
$149 nightly
The price is $166
Nov 8 - Nov 9
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (129)
"It's a beautiful little place with a wonderful owner. Rooms are clean and a good price"
United States
Gail
$131 nightly
The price is $147
Nov 21 - Nov 22
Total with taxes and fees
Micosta Leisure Inn
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
$166 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
1 bedroom, iron/ironing board, WiFi, bed sheets
NEW Cozy Apt Bright + Modern W/D

NEW Cozy Apt Bright + Modern W/D

Hudson Park
8.8 out of 10, Excellent, (26)
"Quiet, safe neighborhood walked three block to the supermarket was able to cook the bed was very comfortable great shower pressure and the place was cleanl, I recommend will be back."
United States
Desiree S.
$166 nightly
The price is $179
Nov 19 - Nov 20
Total with taxes and fees
NEW Cozy Apt Bright + Modern W/D
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"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...
United States
Jim O.
$1,026 nightly
The price is $1,111
Nov 18 - Nov 19
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
$262 nightly
The price is $291
Nov 11 - Nov 12
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Nov 14 - Nov 15
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
The Bluebirds Nest

The Bluebirds Nest

Washington Square
7.4 out of 10, Good, (8)
"We were unimpressed with our stay at The Bluebird’s Nest. Outside of quick responsiveness for WiFi details, the experience wasn’t good. The apartment felt lived in with food in the refrigerator and dirty dishes in the dishwasher. There was garbage piled up under the stairs to the front door, electrical boxes with exposed wires and cracks around the tub. The beds and bedding were very uncomfortable (hard, hot and noisy). We would not stay again."
United States
Tim W.
$111 nightly
The price is $120
Dec 5 - Dec 6
Total with taxes and fees
The Bluebirds Nest
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

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

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Smart TV, books
Chic Madison Parkview

Chic Madison Parkview

Albany
9.6 out of 10, Exceptional, (27)
"Good location and well kept"
United States
Steve J.
$162 nightly
The price is $175
Nov 10 - Nov 11
Total with taxes and fees
Chic Madison Parkview
Outdoor banquet area
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
8.8 out of 10, Excellent, (6)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
$533 nightly
The price is $540
Nov 8 - Nov 9
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds
The Lakeshore House

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
$716 nightly
The price is $802
Nov 8 - Nov 9
Total with taxes and fees
The Lakeshore House
Dining tables
2 bed room Apartment

2 bed room Apartment

South End
10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
$165 nightly
The price is $178
Nov 9 - Nov 10
Total with taxes and fees
2 bed room Apartment
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee
9.6 out of 10, Exceptional, (16)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
United States
Annie C.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
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

Find out more about Brainard

Everything you need to know about Brainard vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Brainard vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brainard vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brainard vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brainard. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Brainard in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Brainard rentals

At Expedia, we put the best Brainard vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Brainard rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brainard vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brainard. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: You might want to consider this vacation home rental near Brainard, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a coffee maker, so you can cook with friends or family. You can relax into your vacation with a garden and foosball.

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 Furnace Brook Winery at Hilltop Orchards.

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.