Brainard Vacation Rentals from AED 257: Search Short-Term Rentals

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Our top choices for Brainard vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Carol

AED 370 total

includes taxes & fees

16 Nov - 17 Nov

A large building with a prominent tower, surrounded by trees and a winding road.

2. Berkshire Mountain Lodge

Pittsfield

Susan J

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

3. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

AED 2,158 total

includes taxes & fees

16 Nov - 17 Nov

4. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robbie S.

AED 2,104 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

AED 778 total

includes taxes & fees

16 Nov - 17 Nov

A white two-story house with a porch, surrounded by trees and a hill.

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

AED 1,498 total

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.

7. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown

Christine P.

AED 867 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Joanna P.

AED 711 total

includes taxes & fees

16 Nov - 17 Nov

A patio with stone flooring, wicker chairs, and a red umbrella. A lake with a dock and a small boat is visible in the background.

9. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

Averill Park

KenD

AED 2,188 total

includes taxes & fees

16 Nov - 17 Nov

A modern building with a wooden deck and a door.

10. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

AED 2,110 total

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin with a porch, a door, and a window.

11. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

AED 589 total

includes taxes & fees

16 Nov - 17 Nov

A cozy room with a large window overlooking a lake, furnished with wicker chairs, a sofa, and a coffee table.

12. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

Averill Park

Mark R.

AED 2,234 total

includes taxes & fees

16 Nov - 17 Nov

A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

13. Sugar Shack - 300 square feet of pure sweetness.

Chatham

Lori S.

AED 1,160 total

includes taxes & fees

16 Nov - 17 Nov

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

14. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

AED 1,160 total

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with a large window, wooden walls, and a television.

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

Hancock

Maura D.

AED 781 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

16. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

AED 772 total

includes taxes & fees

16 Nov - 17 Nov

A rustic cabin interior with a stone fireplace, wooden beams, a bar area, and a cozy seating arrangement.

17. A stunning, modern Lodge with rustic charm at June Farms!

West Sand Lake

LisaL

AED 1,983 total

includes taxes & fees

16 Nov - 17 Nov

A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

18. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

AED 781 total

includes taxes & fees

16 Nov - 17 Nov

A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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

Hancock

Ann

AED 781 total

includes taxes & fees

16 Nov - 17 Nov

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

20. NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

Molly K.

AED 2,043 total

includes taxes & fees

9 Dec - 10 Dec

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Find vacation rentals that suit your style

Top Brainard Hotel Reviews

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A hotel with a covered entrance, stone facade, and arched windows.

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

10/10 Excellent

Jenny

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Gregory

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A modern living room with a fireplace, a large TV, and a seating area with a blue sofa and armchairs.

Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Rensselaer

10/10 Excellent

Keyhoon

A garden with a stone wall, various plants, and a small shed.

Gardner Farm Inn

Troy

10/10 Excellent

My daughter and I were in town for one night to tour RPI. We certainly chose well with our overnight accommodations. Although the house is quaint, extra clean, and decorated perfectly, the star of our stay was the innkeeper, John. From the moment we walked in, it was like seeing an old friend. John was friendly, kind and took excellent care of us. His hospitality made us want to come back again....very soon.

Victoria

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.

Brainard Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Brainard vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

4. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

5. 1800s Carriage house in Berkshires / Hudson Valley

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

7. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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

9. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

10. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

11. Taborton Harvest Boulder Pines Cabin in the woods

12. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

13. Sugar Shack - 300 square feet of pure sweetness.

14. BLUSH: Boutique TINY home*private spa*walk to town

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

16. Berkshires Apartment at the Stephentown Hotel

17. A stunning, modern Lodge with rustic charm at June Farms!

18. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

20. NEW RENO Historic Creamery in Berkshires w/hot tub

Find vacation rentals that suit your style

Top Brainard Hotel Reviews

Inn at Silver Maple Farm

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Brainard?

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

What’s there to see and do in Brainard?

What’s a vacation rental in Brainard like?

14. BLUSH: Boutique TINY homeprivate spawalk to town