Monterey, MA

Hupi Hills | town beach • Kayaks • shared court's

3 bedrooms4 beds3 baths6 guests5.0 (55)

About the property

This house is located in peaceful Monterey less than a miles walk from the lake. Relax and unwind on the lovely grounds, cook up some food for friends out on the back patio, or take a short drive down to the town beach where a couple of kayaks will be waiting for you. After your paddle, rinse off in the outdoor shower and finish the night off outside by the fire. Doesn't get much better than this home nestled right into the lakeside community that is Monterey.

✔ High-speed Wi-Fi (1 gbps)
✔ TV
✔ Full kitchen
✔ Washer & dryer
✔ Free parking
✔ Shared tennis and pickleball court
✔ Large private grass yard
✔ Outdoor firepit
✔ Kayaks
✔ Pack n Play Travel Crib (Upon request)

➥ 3 min to Lake Garfield Beach
➥ 8 mins to Beartown State Forest
➥ 13 mins to Ski Butternut
➥ 18 mins to The Mahaiwe
➥ 20 mins to The Berkshire Theatre
➥ 20 mins to The Lion's Den
➥ 21 mins to W.E.B. Du Bois National Historic Site
➥ 27 mins to Norman Rockwell Museum

✦BEDS & BATHS✦
Inside we have 3 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.

Room Breakdown:
Main Bedroom - 2 Twin beds
Bedroom 2 - 1 Queen bed
Bedroom 3 - 1 Queen bed

All Berkshire Vacation Rental Co.™ Properties include:

  • Support from full-time local team available daily from 9am to 9pm
  • Professional housekeeping & property inspection prior to guest arrival
  • Towels, linens, and bath products
  • At least a mornings worth of coffee to get you started
  • Learn more @berkshirevacationrental

Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.

• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.

To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.

There is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.

Please note that clay tennis court directly on the property is not available for guests. There is a shared tennis court two lots down for guests to use.

This house is located in peaceful Monterey less than a miles walk from the lake. Relax and unwind on the lovely grounds, cook up some food for friends out on the back patio, or take a short drive down to the town beach where a couple of kayaks will be waiting for you. After your paddle, rinse off in the outdoor shower and finish the night off outside by the fire. Doesn't get much better than this home nestled right into the lakeside community that is Monterey.

✔ High-speed Wi-Fi (1 gbps)
✔ TV
✔ Full kitchen
✔ Washer & dryer
✔ Free parking
✔ Shared tennis and pickleball court
✔ Large private grass yard
✔ Outdoor firepit
✔ Kayaks
✔ Pack n Play Travel Crib (Upon request)

➥ 3 min to Lake Garfield Beach
➥ 8 mins to Beartown State Forest
➥ 13 mins to Ski Butternut
➥ 18 mins to The Mahaiwe
➥ 20 mins to The Berkshire Theatre
➥ 20 mins to The Lion's Den
➥ 21 mins to W.E.B. Du Bois National Historic Site
➥ 27 mins to Norman Rockwell Museum

✦BEDS & BATHS✦
Inside we have 3 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.

Room Breakdown:
Main Bedroom - 2 Twin beds
Bedroom 2 - 1 Queen bed
Bedroom 3 - 1 Queen bed

All Berkshire Vacation Rental Co.™ Properties include:

  • Support from full-time local team available daily from 9am to 9pm
  • Professional housekeeping & property inspection prior to guest arrival
  • Towels, linens, and bath products
  • At least a mornings worth of coffee to get you started
  • Learn more @berkshirevacationrental

Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.

• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.

To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.

There is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.

Please note that clay tennis court directly on the property is not available for guests. There is a shared tennis court two lots down for guests to use.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$476Not Available2
Jul 18, 2026$489Not Available2
Jul 19, 2026$298Not Available2
Jul 20, 2026$324Not Available3
Jul 21, 2026$312Not Available3
Jul 22, 2026$314Not Available3
Jul 23, 2026$352Not Available3
Jul 24, 2026$440Not Available3
Jul 25, 2026$443Not Available3
Jul 26, 2026$361Not Available3
Jul 27, 2026$355Not Available3
Jul 28, 2026$350Not Available3
Jul 29, 2026$356Not Available3
Jul 30, 2026$349Not Available3
Jul 31, 2026$435Not Available3
Aug 1, 2026$436Not Available3
Aug 2, 2026$399Not Available4
Aug 3, 2026$399Not Available4
Aug 4, 2026$399Not Available4
Aug 5, 2026$399Not Available4
Aug 6, 2026$399Not Available4
Aug 7, 2026$399Not Available4
Aug 8, 2026$399Not Available4
Aug 9, 2026$399Not Available4
Aug 10, 2026$399Not Available4
Aug 11, 2026$399Not Available4
Aug 12, 2026$399Not Available4
Aug 13, 2026$399Not Available4
Aug 14, 2026$399Not Available4
Aug 15, 2026$399Not Available4
Aug 16, 2026$399Not Available4
Aug 17, 2026$399Not Available4
Aug 18, 2026$399Not Available4
Aug 19, 2026$399Not Available4
Aug 20, 2026$399Not Available4
Aug 21, 2026$399Not Available4
Aug 22, 2026$399Not Available4
Aug 23, 2026$399Not Available4
Aug 24, 2026$399Not Available4
Aug 25, 2026$372Not Available4
Aug 26, 2026$370Not Available4
Aug 27, 2026$399Not Available4
Aug 28, 2026$399Not Available4
Aug 29, 2026$399Not Available4
Aug 30, 2026$399Not Available4
Aug 31, 2026$352Not Available4
Sep 1, 2026$310Not Available4
Sep 2, 2026$303Not Available4
Sep 3, 2026$338Not Available4
Sep 4, 2026$399Not Available4
Sep 5, 2026$399Not Available4
Sep 6, 2026$399Not Available4
Sep 7, 2026$303Not Available4
Sep 8, 2026$272Not Available4
Sep 9, 2026$268Not Available4
Sep 10, 2026$293Not Available4
Sep 11, 2026$352Not Available4
Sep 12, 2026$355Not Available4
Sep 13, 2026$307Not Available4
Sep 14, 2026$272Not Available4
Sep 15, 2026$256Not Available4
Sep 16, 2026$256Not Available4
Sep 17, 2026$287Not Available4
Sep 18, 2026$352Not Available4
Sep 19, 2026$352Not Available4
Sep 20, 2026$297Not Available4
Sep 21, 2026$268Not Available4
Sep 22, 2026$255Not Available4
Sep 23, 2026$259Not Available4
Sep 24, 2026$299Not Available4
Sep 25, 2026$387Not Available4
Sep 26, 2026$390Not Available4
Sep 27, 2026$317Not Available4
Sep 28, 2026$278Not Available4
Sep 29, 2026$270Not Available4
Sep 30, 2026$379Not Available4
Oct 1, 2026$379Not Available4
Oct 2, 2026$399Not Available4
Oct 3, 2026$399Not Available4
Oct 4, 2026$399Not Available4
Oct 5, 2026$399Not Available4
Oct 6, 2026$399Not Available4
Oct 7, 2026$389Not Available4
Oct 8, 2026$391Not Available4
Oct 9, 2026$399Not Available4
Oct 10, 2026$399Not Available4
Oct 11, 2026$399Not Available4
Oct 12, 2026$334Not Available4
Oct 13, 2026$306Not Available4
Oct 14, 2026$312Not Available4
Oct 15, 2026$378Not Available4

Amenities

Beach access
Fire pit
Outdoor fireplace
Patio
Balcony
Lake view
Dryer
Pack n play

5.0 · 55 reviews

G
Gregory
1 week ago

This house was a pleasure to stay in and the neighborhood was extremely relaxing. It was perfect for a weekend away, and only about 25 minutes from Tanglewood concerts. Would definitely stay again.

P
Paul
4 weeks ago

Jaryn was very responsive and his home in Monterey was beautiful and clean. Really enjoyed the stay

D
David
June 2026

Away from it all, yet close to everything via beautiful country roads.

Where you'll be

Monterey, MA, 01245, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 11:00 AM.
Maximum 6 guests.