Luxury Lakefront Vacation Rentals in Monterey

Luxury Lakefront 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 lakefront vacation rentals – enter your dates for availability.

Top-rated lakefront vacation rentals in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

Welcome to the lakeside at Monterey

Welcome to the lakeside at Monterey

Wake to glassy water and pine-scented air at our luxury lakefront vacation rentals in Monterey, Massachusetts. With Wander, you get the polish of a luxury hotel and the privacy of a Berkshire lake house in one flawless stay.
Set right on the shorelines of Monterey's serene lakes, each home pairs inspiring water views with generous indoor and outdoor living. Expect ultrafast WiFi, pristine cleaning, smart-home comforts, and 24/7 concierge support. Settle in knowing your lakeside retreat will look and feel exactly like the photos.

Popular lakefront vacation rentals in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

New lakefront vacation rentals in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

Highlights in Monterey

Experience the quiet charm of the Berkshires with Monterey's pristine lakes, historic homesteads, and scenic mountain trails.
Lake Garfield
Beartown State Forest
Bidwell House Museum
Benedict Pond
Ashintully Gardens
Ski Butternut

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Monterey

Home in Monterey property photo 1

Home in Monterey

4 bedrooms•2 baths
1,421 US dollars for 2 nights•

~$120 less than other sites

Home in Monterey property photo 1

Home in Monterey

3 bedrooms•3.5 baths
1,037 US dollars for 2 nights•

~$90 less than other sites

View all homes

Most popular amenities for lakefront vacation rentals in Monterey

Waterfront (2)
Lake access (1)
Sound system (1)
Bbq area (2)
Fire place (2)
Dryer (2)
Washer (2)
Oven (2)
Kitchen (2)
Tv (2)
Microwave (2)
Wifi (2)
Dishwasher (2)
Heating (2)
Coffee maker (2)
Air conditioning (2)

Other popular amenities & vacation types in Monterey

Pet-friendly vacation rentals in Monterey
Family vacation rentals in Monterey
Discover more lakeside charm in Monterey

Discover more lakeside charm in Monterey

Monterey sits at the heart of the southern Berkshires, where clear lakes meet quiet hemlock forests. Lake Garfield glimmers in town, while Beartown State Forest and Benedict Pond offer peaceful trails and swims in summer.
Autumn brings blazing foliage reflected on the water. Winter delivers crisp mornings and downhill runs at Ski Butternut just up the road, with cozy evenings by the fire. Great Barrington is minutes away for galleries, boutiques, and a lively arts calendar.
All of this makes Wander's luxury lakefront vacation rentals in Monterey, Massachusetts the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Monterey

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

Wander offers a level of consistency and quality you won’t find with most lakefront 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 lakefront vacation rentals in Monterey?

Some of our most popular lakefront 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 lakefront vacation rentals does Wander have available in Monterey?

Wander offers 2 lakefront 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 lakefront vacation rentals in Monterey?

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

Do Wander’s lakefront 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.