
Family-friendly holiday rentals in Monterey
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Monterey
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Bidwell Landing | Lakefront • Spacious
Enjoy this spacious 4 bed, 4 bath home nestled on Lake Garfield in the beautiful Berkshires. Well-curated, clean, and perfect for entertaining, with expansive outdoor decks on multiple levels. Surrounded by pine forest and overlooking the lake, the property features a stunning dock, creating an ideal retreat for family and friends. A serene, nature-filled escape with luxurious comfort and breathtaking views all just a short drive from Great Barrington, Smithsonian's #1 small town in the country.

The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Kitchenette|King Bed|Couch
Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58" Smart TV

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Jaw dropping mountain & lake views
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

The Cottage at The Barrington House
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Walk to Town! Great Barrington 4-bedroom farmhouse
Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Swim Lake , Hikes, Sleeps 12, Fast WiFi
Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * 5 mins to Swim lake, kayaking & fishing. * Great Hikes from the house * Jacobs Pillow & Tanglewood 20 mins * Historic Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Fast Wifi * Fireplace * Butternut ski 15 mins * Pets welcome

Berkshires Cottage | Trails & Water Nearby
★☆ ABOUT OUR HOME ☆★ Family-friendly rustic-modern getaway set on 4 private acres in the heart of the Berkshires. We designed this home as a peaceful escape from busy city life—welcome! Whether you're here to unplug, explore, or stay connected while working remotely, you’ll find comfort, charm, and convenience in every corner.

Charming cottage w/ gorgeous views.
Quintessential wooden cottage w/ 2 BR, 2 full baths & open floor plan. Enjoy the glass enclosed sun room overlooking mature perennial gardens or walk the carved path through the field of wild flowers. Fully furnished, utilities included.
Popular amenities for Monterey family-friendly rentals
Family-friendly home rentals with a hot tub

Artist Cottage

Relaxing secluded stay with loving social animals.

Boutique TINY home+private HOT TUB-walk to Main St

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Stylish Pet-Friendly Retreat w/ Hot Tub

Charming Lakefront Cabin with Hot Tub

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

The Red Cabin-Secluded Getaway with backyard Brook
Family- and pet-friendly home rentals

3-bedroom Berkshire bungalow on 2.5 peaceful acres

The East Street Cabin

Peaceful Cabin in the Woods

Harvey Mountain Lodge by State Forest

Cool Cozy Cabin by the Lake

Scandinavian Cottage/Mountain Views/Fire pit

Modern Copake Falls Getaway - 8 Mins to Catamount

Pine Plains Cottage
Family-friendly home rentals with a pool

Country Getaway Tiny House in woods w/Pool/Sauna

The Copake Cabin - A rustic-modern retreat.

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Cozy cottage with pool, walking distance to lake

Modern Upstate Cabin, near Rhinebeck NY

Le Soleil Suite - Pool, Mtn Views Near Hudson
When is the best time to visit Monterey?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £246 | £232 | £241 | £218 | £226 | £265 | £291 | £290 | £275 | £255 | £238 | £240 |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Monterey

Total holiday rentals
Explore 60 holiday rentals in Monterey

Nightly prices starting at
Monterey holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 3,100 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Monterey holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Monterey rentals

4.9 Average rating
Monterey stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a patio Monterey
- Rentals with lake access Monterey
- Rentals with a washing machine and dryer Monterey
- Pet-friendly rentals Monterey
- Rentals with a kayak Monterey
- Waterfront rentals Monterey
- Rentals with a firepit Monterey
- Rentals with a fireplace Monterey
- Rentals with outdoor seating Monterey
- House rentals Monterey
- Family-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Mount Southington Ski Area
- Ski Sundown
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- June Farms
- Hancock Shaker Village
- Poets' Walk Park
- Millbrook Vineyards & Winery
- New York State Museum
- MVP Arena
- Rensselaer Polytechnic Institute
- Mount Greylock




