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)
May 19, 2026$189Available2
May 20, 2026$189Available2
May 21, 2026$189Not Available2
May 22, 2026$317Not Available3
May 23, 2026$321Not Available3
May 24, 2026$317Not Available3
May 25, 2026$203Not Available2
May 26, 2026$189Available3
May 27, 2026$189Available3
May 28, 2026$191Available3
May 29, 2026$229Available3
May 30, 2026$249Available3
May 31, 2026$204Available3
Jun 1, 2026$198Available3
Jun 2, 2026$198Available3
Jun 3, 2026$240Not Available3
Jun 4, 2026$221Not Available3
Jun 5, 2026$271Not Available3
Jun 6, 2026$278Not Available3
Jun 7, 2026$241Not Available4
Jun 8, 2026$246Not Available3
Jun 9, 2026$243Available3
Jun 10, 2026$244Available3
Jun 11, 2026$259Available3
Jun 12, 2026$329Available3
Jun 13, 2026$334Available3
Jun 14, 2026$285Available3
Jun 15, 2026$259Available3
Jun 16, 2026$256Available3
Jun 17, 2026$264Available3
Jun 18, 2026$279Available3
Jun 19, 2026$324Available3
Jun 20, 2026$332Available3
Jun 21, 2026$260Available3
Jun 22, 2026$242Available3
Jun 23, 2026$248Available3
Jun 24, 2026$265Available3
Jun 25, 2026$300Available3
Jun 26, 2026$410Available3
Jun 27, 2026$476Available3
Jun 28, 2026$359Available3
Jun 29, 2026$272Available3
Jun 30, 2026$275Available3
Jul 1, 2026$361Available4
Jul 2, 2026$499Available4
Jul 3, 2026$499Available4
Jul 4, 2026$499Available4
Jul 5, 2026$376Available4
Jul 6, 2026$364Available3
Jul 7, 2026$327Available3
Jul 8, 2026$332Available3
Jul 9, 2026$341Available3
Jul 10, 2026$386Not Available3
Jul 11, 2026$364Not Available3
Jul 12, 2026$318Not Available3
Jul 13, 2026$291Not Available3
Jul 14, 2026$283Available3
Jul 15, 2026$282Available3
Jul 16, 2026$323Available3
Jul 17, 2026$443Available3
Jul 18, 2026$499Available3
Jul 19, 2026$347Available3
Jul 20, 2026$322Available3
Jul 21, 2026$347Available3
Jul 22, 2026$316Available3
Jul 23, 2026$353Available3
Jul 24, 2026$442Available3
Jul 25, 2026$441Available3
Jul 26, 2026$363Available3
Jul 27, 2026$351Available3
Jul 28, 2026$318Available3
Jul 29, 2026$354Available3
Jul 30, 2026$347Available3
Jul 31, 2026$430Available3
Aug 1, 2026$430Available3
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

Where you'll sleep

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

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.