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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 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


Chesterfield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 7
  • Min. age of primary renter: 35
  • Children welcome
  • 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.


Exceptional! 5/5 -
(8 traveler reviews)

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Beautiful Mountaintop Retreat In The Country!
average rating of 5.0 based on 8 reviews

Wonderful Family House

  • 5 of 5

What an incredible home, the owner thought of every possible detail! We were provided with excellent details that we would need to facilitate our stay. The house was immaculate. The kitchen was stocked with the tools to enable you to cook there. There were two comfortable rooms on the first floor, as well as a formal dining room. The bedrooms on the second floor were decorated beautifully. Bedding was very comfortable, and there was an ample supply of extra blankets and quilts to ensure a perfect night's sleep.

As wonderful as the house was, the grounds were equally amazing. There was a deck, an area with adirondack chairs. There is even a beaver pond on the property and along the trail to get to the pond, there are frogs and newts- it was awesome.

If you are looking for the perfect place, this is it!

  • Submitted: Sep 18, 2017
  • Stayed: September 2017
  • Source: HomeAway
Owner's Response: Thank you for your lovely review Betsy. We are delighted you and your family had an enjoyable stay!
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Perfect relaxation in a charming place

  • 5 of 5

The extended family who let the property to us were very welcoming and went out of their way to make us feel at ease. The property itself is a well kept very good sized family house which is actually lived in by the family for part of the year - it is not the sort of place where you arrive and find simply the obligatory six plates, six cups and six forks with everything else bare.

It is on a small family estate (in the English rather than the property developer sense) but you are several hundred yards and a few hundred trees away from the other houses so you have peace and as much of your own space as you could wish for. The extensive lawns, running over many acres are a particular benefit whilst the beaver pond a short walk through the wood is stunningly beautiful.

  • Submitted: Aug 11, 2017
  • Stayed: August 2017
  • Source: HomeAway
Owner's Response: Thank you William for your lovely review! We are delighted you and your family had an enjoyable vacation.
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Philadelphia PA

Wonderful for tranquil getaway

  • 5 of 5

Our family of four had a lovely week's stay at this house in July. Setting is beautiful and quiet (last house on road - no traffic noise of any kind), and the house itself is roomy and comfortable. We had short visits by extended family and friends during our stay, and there was ample room. Maureen's pictures on the walls and the books in the bookcases make the house feel like a home, which we appreciated. We had several questions during our stay, and Tim or Maureen were always helpful and quick to respond. Tim's Dad who lives down the road was a gracious host as well. House is close enough to Cummington Creamery and Worthington General Store that you don't have to drive all the way to Northampton if you forgot an ingredient. Chesterfield Gorge is a lovely place to walk, and we had fun walking down to the beaver ponds behind the house. Great place for a low key country vacation with family and friends, reading, cooking, hiking, star-gazing and catching up; and, if willing to drive a bit, fairly easy access to a range of activities in Western Mass (Mass MOCA, Shakespeare at the Mount, Historic Deerfield, etc.).

  • Submitted: Jul 12, 2017
  • Stayed: June 2017
  • Source: HomeAway
Owner's Response: Thanks for your lovely review. So happy you enjoyed your stay!
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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: December 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: August 2016
  • Source: VRBO, from HomeAway
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Mo Ryan
Member since: 2014
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
December 1, 2017

Why Mo Ryan chose Chesterfield

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.



Rates & Availability

Taxes and fees are additional

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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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