Monterey, MA

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

3 bedrooms 4 beds 3 baths 6 guests 5.0 (25)

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.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Jun 2, 2026$189Available3
Jun 3, 2026$189Not Available3
Jun 4, 2026$221Not Available3
Jun 5, 2026$271Not Available3
Jun 6, 2026$278Not Available3
Jun 7, 2026$241Not Available4
Jun 8, 2026$211Not Available3
Jun 9, 2026$210Available3
Jun 10, 2026$209Available3
Jun 11, 2026$220Available3
Jun 12, 2026$263Available3
Jun 13, 2026$270Available3
Jun 14, 2026$238Available3
Jun 15, 2026$227Available3
Jun 16, 2026$225Available3
Jun 17, 2026$232Available3
Jun 18, 2026$270Available3
Jun 19, 2026$315Available3
Jun 20, 2026$321Available3
Jun 21, 2026$263Available3
Jun 22, 2026$245Available3
Jun 23, 2026$253Available3
Jun 24, 2026$280Available3
Jun 25, 2026$277Not Available3
Jun 26, 2026$373Not Available3
Jun 27, 2026$415Not Available3
Jun 28, 2026$383Not Available3
Jun 29, 2026$292Not Available3
Jun 30, 2026$355Not Available3
Jul 1, 2026$405Not Available4
Jul 2, 2026$499Not Available4
Jul 3, 2026$499Not Available4
Jul 4, 2026$499Not Available4
Jul 5, 2026$430Not Available4
Jul 6, 2026$417Available3
Jul 7, 2026$379Available3
Jul 8, 2026$389Available3
Jul 9, 2026$395Available3
Jul 10, 2026$386Not Available3
Jul 11, 2026$364Not Available3
Jul 12, 2026$318Not Available3
Jul 13, 2026$349Not Available3
Jul 14, 2026$338Available3
Jul 15, 2026$333Available3
Jul 16, 2026$381Available3
Jul 17, 2026$499Not Available3
Jul 18, 2026$499Not Available3
Jul 19, 2026$380Not Available3
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

Amenities

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

5.0 · 25 reviews

G
Gary D.
April 2026

very quite place.

M
Maggie D.
March 2026

We had a fantastic getaway at Jaryn’s place. Everything was extremely clean and homey, great kitchen and comfortable furniture and spaces. The house is located in a peaceful spot with quiet surroundings and beautiful neighborhood views. Can’t recommend it enough.

S
Sheila J.
February 2026

We had a lovely stay in the Berkshires at Jaryn’s place. It was very clean and perfect for a family with small children.

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

Contact us for cancellation policy details prior to booking.

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.