Luxury Vacation Rentals in Monterey

Luxury Vacation Rentals in Monterey

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 2 vacation rentals – enter your dates for availability.
Welcome to Monterey

Welcome to Monterey

Explore our elevated collection of luxury vacation rentals in Monterey, a quiet corner of the Berkshires designed for restorative time away. With Wander, you get the polish of a hotel and the privacy of a beautifully run home, so every stay is effortless.
Settle into serene lakeview escapes and forest-edge retreats where mornings start on sunlit decks and evenings wrap beside a crackling fireplace. Expect ultra fast WiFi, spa-grade linens, pristine cleaning, and 24/7 concierge support. Select homes add chef-ready kitchens, dedicated workspaces, and private hot tubs or pools, making it easy to blend work and play in absolute comfort.

All homes in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms2 baths
1,421 US dollars for 2 nights

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms3.5 baths
1,037 US dollars for 2 nights

~$90 less than other sites

View all homes

Highlights in Monterey

Immerse yourself in the quiet beauty of the Berkshires with pristine lakes, historic homesteads, and scenic mountain trails in Monterey.
Beartown State Forest
Lake Garfield
The Bidwell House Museum
Ski Butternut
Otis Ridge

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Discover more of Monterey

Discover more of Monterey

Framed by Beartown State Forest and sparkling Lake Garfield, Monterey serves up classic Berkshire scenery without the crowds. Paddle calm coves in summer, swim at the town beach, or circle Benedict Pond on a gentle trail lined with hemlock and maple.
Autumn brings blazing hillsides and harvest markets. Winter invites laid-back laps at nearby Ski Butternut and quiet cross-country tours through snow-dusted woods. Minutes away, Great Barrington and Stockbridge offer galleries and live music, and the Bidwell House Museum anchors local history in town.
This rare mix of wild spaces and culture makes Monterey a four-season favorite. It is exactly why Wander’s luxury vacation rentals in Monterey are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Monterey

Why should I book a Wander in Monterey over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Monterey delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Monterey?

Some of our most popular vacation rentals in Monterey include Laurel Banks Waterfront, Lake Garfield Waterfront, and Laurel Banks Waterfront. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Monterey?

Wander offers 2 vacation rentals in Monterey, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Monterey?

You can check-in to Wander vacation rentals in Monterey after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Monterey have WiFi access?

Yes. Every Wander home in Monterey has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.