Family Friendly Properties

Family Friendly Properties2024-04-11T19:40:45-04:00

Ping pong, pool tables, board games, puzzles, video games, yard games. So many things to do at your vacation rental, you may never leave! Pack ‘n plays and highchairs available upon request.

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Lake Rentals in the Berkshires

Mountain View Victorian Retreat

Walk to Town, Minutes to Mass MoCA, Mountain Views
3 Bedroom ∙ 4 Beds ∙ 1.5 Bathrooms ∙ 6 Guests

Lake Rentals in the Berkshires

Hidden Oasis in the Mountains

Hot Tub, Mountain Views, Family Friendly
5 Bedroom ∙ 8 Beds ∙ 3 Bathrooms ∙ 10 Guests

Rentals in the Berkshires

Mountain View Retreat with Hot Tub

Hot Tub, Mountain Views, Accessible
4 Bedroom ∙ 4 Beds ∙ 2.5 Bathrooms ∙ 7 Guests

Rentals in the Berkshires

Idyllic Retreat with Hot Tub/Sauna

Hot Tub, Dry Sauna, Full Gym, 7 Minutes to Downtown Great Barrington
3 Bedroom ∙ 4 Beds ∙ 3 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

Berkshires Escape with Pool

Heated Pool, Centrally Located, Modern Design
4 Bedroom ∙ 5 Beds ∙ 3 Bathrooms ∙ 8 Guests

Rental with pool in the Berkshires

Mountain Blossom Retreat

Heated Pool, Hot Tub, Full Gym, Mountain Views, 60 Private Acres
3 Bedroom ∙ 4 Beds ∙ 3.5 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

Family-Centric Berkshire Getaway

Centrally Located, Family Friendly, 1st Floor Bedroom & Bath
4 Bedroom ∙ 4 Beds ∙ 2 Bathrooms ∙ 7 Guests

Rentals in the Berkshires

Charming Berkshires Cottage

Pet Friendly, Rural, 10 Minutes to Great Barrington
2 Bedroom ∙ 3 Beds ∙ 1.5 Bathrooms ∙ 4 Guests

Lake Rentals in the Berkshires

Glorious Lakefront Retreat

Lakefront, Water Activities, Family Friendly
3 Bedroom ∙ 5 Beds ∙ 2.5 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Central Berkshire Bungalow

Family Friendly, Centrally Located
3 Bedroom ∙ 4 Beds ∙ 2 Bathrooms ∙ 5 Guests

Lake Rentals in the Berkshires

Berkshires Log Cabin

Log Cabin, Private, Town Beach Access, 1st Floor Bedroom & Bathroom
2 Bedroom ∙ 4 Beds ∙ 2 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Best of the Berkshires with Hot Tub

Renovated, Hot Tub, Minutes to Great Barrington, One Level Living
2 Bedroom ∙ 2 Beds ∙ 1 Bathrooms ∙ 4 Guests

Rentals in the Berkshires

Lenox Grand Colonial with Pool

Pool, 10 Minutes to Tanglewood, Family Friendly
4 Bedroom ∙ 4 Beds ∙ 2.5 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

The Berkshires Woodland Estate

Heated Pool, Rural, Minutes to Jacob’s Pillow, Hiking
4 Bedroom ∙ 6 Beds ∙ 4 Bathrooms ∙ 9 Guests

Rentals in the Berkshires

West Stockbridge Sanctuary

Close to Town, Minutes to Tanglewood, Family Friendly
3 Bedroom ∙ 4 Beds ∙ 2 Bathrooms ∙ 6 Guests

Lake Rentals in the Berkshires

Chic Berkshire Retreat

10 Minutes to Jiminy Peak, 5 Minutes to Greylock, Pet Friendly
3 Bedroom ∙ 4 Beds ∙ 1.5 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Little House in the Woods

10 Minutes to Great Barrington, Pet Friendly, One Level Living
2 Bedroom ∙ 3 Beds ∙ 2 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Panoramic Views, Indoor Pool

Heated Indoor Pool, Panoramic Views, 10 Minutes to Tanglewood
4 Bedroom ∙ 6 Beds ∙ 4.5 Bathrooms ∙ 11 Guests

Rentals in the Berkshires

Renovated Private Guest House

Pet Friendly, Minutes to Great Barrington, Family Friendly
2 Bedroom ∙ 3 Beds ∙ 1.5 Bathrooms ∙ 5 Guests

Rentals in the Berkshires

Berkshires Lakefront Retreat

Lakefront, Mountain Views, Close to Jiminy Peak, Family & Pet Friendly
4 Bedroom ∙ 5 Beds ∙ 2.5 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

Renovated Pittsfield Colonial

Centrally located, Family & Pet Friendly
4 Bedroom ∙ 8 Beds ∙ 2.5 Bathrooms ∙ 12 Guests

Rentals in the Berkshires

Historic House on the Hill

Minutes to Mass MoCA, Family Friendly
3 Bedroom ∙ 4 Beds ∙ 1.5 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Sophisticated Lenox Retreat

Minutes to downtown Lenox & Tanglewood, Family Friendly
4 Bedroom ∙ 4 Beds ∙ 2.5 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

Woodland Haven with Heated Pool

Heated Pool, Rural, Minutes to Jacob’s Pillow, Hiking
2 Bedroom ∙ 3 Beds ∙ 3 Bathrooms ∙ 4 Guests

Rentals in the Berkshires

Hillsdale Mountain View Estate

Mountain Views, Family & Pet Friendly, Rural
7 Bedroom ∙ 11 Beds ∙ 5 Bathrooms ∙ 12 Guests

Rentals in the Berkshires

Berkshires Retreat with Sauna

Cedar Barrel Sauna, Pet Friendly, Hiking, Town Beach Access
2 Bedroom ∙ 7 Beds ∙ 1.5 Bathrooms ∙ 7 Guests

Rentals in the Berkshires

The Penthouse, Downtown Lenox

Downtown Lenox, Beautifully Renovated, Pet Friendly, Minutes to Tanglewood
3 Bedroom ∙ 4 Beds ∙ 2 Bathrooms ∙ 8 Guests

Rentals in the Berkshires

Elegant Mountain View Retreat

Mountain Views, Sauna, Close to Jiminy Peak, Family & Pet Friendly
3 Bedroom ∙ 5 Beds ∙ 3 Bathrooms ∙ 8 Guests

Lake Rentals in the Berkshires

Modern, Renovated Lakefront Escape

Lakefront, Scenic Views, Family Friendly
4 Bedroom ∙ 6 Beds ∙ 3 Bathrooms ∙ 9 Guests

Rentals in the Berkshires

Berkshires Estate w/ Heated Pool

Heated Pool, Minutes to Butternut & Downtown Great Barrington, Family Friendly
5 Bedroom ∙ 7 Beds ∙ 4.5 Bathrooms ∙ 10 Guests

Rentals in the Berkshires

The Guest House at Cottage Farm

Beautifully Renovated, Family Friendly, Hiking, Centrally located
3 Bedroom ∙ 4 Beds ∙ 3 Bathrooms ∙ 6 Guests

Rentals in the Berkshires

Berkshires Colonial on 2 Acres

Centrally Located, Family Friendly
5 Bedroom ∙ 7 Beds ∙ 2.5 Bathrooms ∙ 10 Guests

Rentals in the Berkshires

Berkshires Estate w/ Heated Pool

Heated Pool, Minutes to Butternut & Downtown Great Barrington, Family Friendly
5 Bedroom ∙ 7 Beds ∙ 4.5 Bathrooms ∙ 10 Guests

Frequently Asked Questions

Where can I find wifi information?2024-01-12T15:19:58-04:00

The wifi information is provided in the online guidebook as well as posted in multiple places throughout the property.

Do you have local recommendations for places to eat, shop, and experience ?2024-01-12T15:19:31-04:00

You will receive a link to a helpful website after booking as well as some personalized recommendations. Additionally, you can find restaurants, shops, hikes, places to visit, and things to do in the guidebook online. There is also a physical copy of the guidebook at the property.

How does the check in process work?2024-01-12T15:18:59-04:00

Booked guests will receive instructions for check-in 1-2 days prior to the start of their reservation either through email or through their booking platform inbox. On the morning of check-in, a code will be sent for the lock box or keyless door lock.

Do you allow pets?2024-01-12T15:18:28-04:00

Many of our properties allow small house trained dogs. Most do not allow multiple and many only accept hypoallergenic dogs. No puppies under 2 yrs of age. A $100 pet fee will be incurred if bringing a pet. Guests are expected to clean up inside and outside after their pet. No pets on furniture. In many cases, you will be asked to crate your dog if left home alone. Pets are not accepted without prior approval.

What is your cancellation policy?2024-01-12T15:17:41-04:00

Full refund for cancellations up to 30 days before check-in. If booked fewer than 30 days before check-in, full refund for cancellations made within 48 hours of booking and at least 14 days before check-in. After that, 50% refund up to 7 days before check-in. No refund after that. May vary for stays over 28 days.

What is supplied?2024-01-12T15:17:10-04:00

Each property is supplied with bed linens, bath towels, cookware, basic kitchen spices, coffee, soap, shampoo, and basic cleaning supplies.

Can I request to check in early or to check out late?2024-01-12T15:16:17-04:00

Check in is 4pm or later and check out is promptly at 11am. Approvals for an early check-in or late check-out will be given a few days prior to your reservation and are contingent on our cleaners schedule and other bookings. A fee may apply.

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