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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful Mountaintop Retreat In The Country!

Bedrooms 4
Half Baths1
Property type house
Minimum Stay 5 - 7 nights


About the property

Peaceful, private setting with gorgeous mountain views! Relaxing and enjoyable!

Lovely 4 Bedroom, 2.5 bath Colonial on several acres of land. It is part of a larger family compound of several hundred acres which includes beaver ponds, brooks, hiking trails, and mountaintop views. Area amenities include hiking, biking, swimming, golfing and canoeing. Chesterfield Gorge is minutes away. Convenient to Northampton, Tanglewood, and Shelburne Falls.

Nature and beauty surround you!

Master bedroom with queen bed and private bathroom. Bedroom #2 has one Double bed. Bedroom #3 has one Double bed and one Single bed. Bedroom #4 has 2 Single beds.

Eat in Kitchen, Seating for 6 people. Oven, Microwave, Refrigerator, Dishwasher, Pantry Items, Coffee maker, Toaster. Dishes & Utensils. Amenities include: washing machine, clothes dryer, iron & board, towels & linens provided.

More Details

Mo Ryan
Member since: 2014
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
July 4, 2017

Why Mo Ryan chose Massachusetts

The home is on top of the mountain, part of a larger family property that consists of several hundred acres of fields and forests.

What makes this house unique

It is a serene retreat, coffee or cocktails on the back deck, or sitting on the mountaintop bench, allows you to rest, relax and re-charge.


Chesterfield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 16:00
  • /
  • Check-out: 11:00
  • Max. occupancy: 7
  • Min. age of primary renter: 35
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • Adventure
  • Away From It All
  • Family
  • Sports & Activities
  • Tourist Attractions
  • Clothes Dryer
  • Fireplace ...
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wood Stove ...
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , shower
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet
  • 4 Bedrooms, Sleeps 7
  • Bedroom 1 - 1 queen
    Bedroom 2 - 2 twin/ single
    Bedroom 3 - 1 queen , 1 twin/ single
    Bedroom 4 - 1 double
  • Books
  • DVD Player
  • Stereo
  • Television ...
  • Bicycles ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Outdoor Grill ...
  • Ski & Snowboard ...
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool ...
  • churches
  • festivals
  • library
  • live theater
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • photography
  • scenic drives
  • shopping
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • golf
  • hiking
  • hot air ballooning
  • hunting
  • mountain climbing
  • skiing
  • swimming
A unique country get away, a mountain top retreat, surrounded by fields, forest, ponds and streams. Located on the Worthington/Chesterfield line, conveniently located to Northampton, Deerfield River Valley, as well as Pittsfield and Tanglewood.


5/5 -
(5 traveler reviews)

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Beautiful Mountaintop Retreat In The Country!
average rating of 5.0 based on 5 reviews

Great spot to get away

  • 5 of 5

My family and I stayed here when we were in town for my niece's graduation at Smith. It was lovely. Everything was in working order and just as described. Mo, the owner, was very responsive and the area was just great. It was unseasonably warm the first day we were there but it cooled off after that. Area was lovely. We recommend the Rapids restaurant about 20 minutes away. Awesome experience.

  • Submitted: May 23, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your lovely review Rosalinda. I'm happy your family had a wonderful time.
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Cambridge, MA

this is our second stay

  • 5 of 5

Last year when we visited, we said we would return and we did. This time we brought extended family with us, which made the house more lively and more efficient. We took advantage of its size and generous resources. It is intended for large groups. We had our white Christmas season, a big snow storm, the trails covered with a deep blanket, beautiful, instant plowing by the town and help with the driveway. We cooked, the kitchen is so well appointed, we made fires, plenty of wood to burn. Next, we have to come in a warmer season to make use of the terrace with its view of the hill and woods. We did not get to see Tim and Maureen but we communicated with them easily, they were available for any question. We enjoy Western Massachusetts, this house's location is perfect for visiting the main places of interest, we were in Lenox, Northampton, Pittsfield, Greenfield, Brattleboro, Amherst, we could easily have gone to Mass MoCa and the trails abound in the area. What a treat. Thank you again for sharing your beautiful house.

  • Submitted: Jan 7, 2017
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Owner's Response: We are very happy you enjoyed your return stay. Thank you for your lovely review.
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spacious, scenic, and smooth

  • 5 of 5

Large, clean house with plenty of room for a family. Four bedrooms, all upstairs - a master bedroom with bath and three smaller (but sizable) bedrooms with a shared bath. Plenty of room downstairs with two living rooms, a dining room, an eat-in kitchen, and another bathroom. Beautiful, expansive property at the end of a long, private road. Broad(ish) band internet and 4G LTE reception (AT&T, at least). We enjoyed sleeping late in the comfortable beds with the cool summer night breeze and waking to a beautiful view of the hills before having coffee on the back deck. The property was fun to explore. The kids liked practicing soccer in the meadow atop the hill and we climbed up to spot shooting stars at night from the hilltop chairs. The house is well equipped and our hosts made our visit easy. We particularly enjoyed our visit from Charlie who shared the history of the property and pointed out several spots for us to check out. We recommend lunch at the Cummington Creamery about 10 minutes away - good baked goods, coffee, and excellent homemade bread.

  • Submitted: Aug 22, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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Cambridge, MA

we fell in love with this house

  • 5 of 5

For us, the property combines the best possible qualities: far enough from urban centers, close enough to touristic places and shopping areas, multiple opportunities for hiking, simple but efficient and tasteful interior, great layout for sharing the place with its 4 BR, 2 LR, 2 and 1/2 bath, comfortable beds, wonderful wood stove well stocked, discrete yet welcoming and truly hospitable hosts. We spent 10 days at the house. We did not want to leave. We met several members of the extended family who live in the area, and because we are half French and most of our relatives are in France, it felt like an opportunity to be part of a family. We definitely will return.

  • Submitted: Jan 9, 2016
  • Stayed: Dec 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for your lovely review! We are so happy you enjoyed your stay~
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Long Island NY

great house, fantastic setting

  • 5 of 5

What a location , house was as expected roomy , clean and well equipped for our 6 day stay . The setting and surrounding property is beautiful, fields with great old stone walls, vistas of the surrounding hills, and even a white eyed dog ( one eye). The trail back to the beaver ponds almost hobbit like with rock outcroppings, ferns and moss. If you have a chance arrange the tour with Charles he will show you other great locations on the property, streams , old farmhouse and barns, sawmill, the old path/road along the stream and the loggers cabin. Be aware, he is like the Walter Houston prospector character in " Treasure of the Sierra Madre", as Bogey said "I didn't know he was part goat". We even found the ruins of one of the old sugar maple shacks. ( Hints: Springfield attraction, Horace Greeley). Other great location in the surrounding areas: We drove the dirt road along the gorge, the blue and yellow food shack, ( great fish tacos) general store, train ride in Look park, went to the Keystone Arches in Chester and a day trip to Mt. Graylock. A great stay, already wanting to go back.

  • Submitted: Aug 26, 2014
  • Stayed: Aug 2014
  • Source: VRBO, from HomeAway
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Rates & Availability

Chesterfield House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Seasonal pricing
Nov 5 2016 - Nov 30 2017
5 night minimum stay
My Standard Rate
7 night minimum stay

Additional information about rental rates

Cleaning Fee $125
Refundable damage deposit $350

No pets or smokers. Check in Friday at 4pm. Check out Friday at 11am.

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
Contact Owner

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