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Beautiful Mountaintop Retreat In The Country!

Chesterfield, MA, USA
  • House2688 sqft
  • Bedrooms4
  • Sleeps7
  • Bathrooms2
  • Half Baths1
  • Minimum Stay5 nights

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.


Mo Ryan

Member Since 2014
Response rate:
Response time:
within one day
Calendar last updated:
Mar 12, 2018
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.


    • Internet
    • Swimming pool
    • Heater
    • Fireplace
    • Kids Welcome
    • Washer & Dryer
    • Parking
    • TV
    • No Smoking


      • 4 Bedrooms, Sleeps 7
      • Bedroom 1
        1 queen
      • Bedroom 2
        2 twin/ single
      • Bedroom 3
        1 queen, 1 twin/ single
      • Bedroom 4
        1 double


        • 2 Bathrooms, 1 Half Bath
        • Bathroom 1
          toilet, shower
        • Bathroom 2
          toilet, shower
        • Bathroom 3


            • Adventure
            • Away From It All
            • Family
            • Sports & Activities
            • Tourist Attractions


                • Guests provide their own meals


                    • Living Room
                    • Clothes Dryer
                    • Heating
                      Home heats with oil/wood furnace
                    • Internet
                      Internet & "wifi" in house
                    • Iron & Board
                    • Linens Provided
                    • Fireplace
                      Woodstove in fireplace with supply of wood
                    • Parking
                      Plenty of parking in driveway and private road
                    • Telephone
                      House phone, land line installed. Cell phones work great at the house.
                    • Towels Provided
                    • Washing Machine
                    • Wood Stove
                      Wood Stove in Den for added warmth in the Winter months


                        • Coffee Maker
                        • Dishes & Utensils
                        • Dishwasher
                        • Kitchen
                          Lovely eat-in kitchen, seats 6-8 people comfortably
                        • Microwave
                        • Oven
                        • Pantry Items
                        • Refrigerator
                        • Stove
                        • Toaster


                            • Dining Area


                                • Books
                                • DVD Player
                                • Stereo
                                • Television
                                  Watch movies, DVD's, Apple TV, and Netflix. Also Direct TV (147 Channels, with local channels) .


                                    • Bicycles
                                      Bring road or mountain bikes, miles of hard and dirt roads to ride and explore. Northampton Bike trail popular with visitors
                                    • Deck / Patio
                                      Lovely back deck with Adirondack Chairs
                                    • Golf
                                      Worthington Golf Course - 2 miles away, a truly enjoyable and memorable course. Dine at the Clubhouse with its 40 mile view.
                                    • Kayak / Canoe
                                      Kayak or canoe at the Dead Branch, Chesterfield, DAR State Forest, Goshen, Littleville Lake, Chester, all within 8 miles.
                                    • Outdoor Grill
                                      Gas Grill available on deck for use
                                    • Ski & Snowboard
                                      Cross Country skiing on property, ice skating on beaver ponds behind house. Downhill skiing in Charlemont, Ma, or Mount Snow in So. Vt.


                                        • wheelchair inaccessible

                                          Pool / Spa

                                            • Private Pool
                                              Built-in swimming pool on family compound. Permission from owner needed before use.


                                                • 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.

                                                                  House Rules

                                                                  Check-in: 4:00 PM

                                                                  Check-out: 11:00 AM

                                                                  Cancellation Policy

                                                                  100% refund if canceled at least 60 days before arrival date. 50% refund if canceled at least 30 days before arrival date. You must contact the owner directly to request cancellation.

                                                                  8 Reviews


                                                                  Latest reviews

                                                                  Wonderful Family House

                                                                  Betsy H.

                                                                  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!

                                                                  Owner's Response:

                                                                  Thank you for your lovely review Betsy.

                                                                  We are delighted you and your family had an enjoyable stay!

                                                                  Perfect relaxation in a charming place

                                                                  William M.

                                                                  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.

                                                                  Owner's Response:

                                                                  Thank you William for your lovely review!

                                                                  We are delighted you and your family had an enjoyable vacation.

                                                                  Wonderful for tranquil getaway

                                                                  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.).

                                                                  Owner's Response:

                                                                  Thanks for your lovely review. So happy you enjoyed your stay!

                                                                  Great spot to get away

                                                                  Rosalinda G.

                                                                  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.

                                                                  Owner's Response:

                                                                  Thank you for your lovely review Rosalinda. I'm happy your family had a wonderful time.

                                                                  this is our second stay

                                                                  nvbCambridge, MA

                                                                  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.

                                                                  Owner's Response:

                                                                  We are very happy you enjoyed your return stay. Thank you for your lovely review.

                                                                  spacious, scenic, and smooth

                                                                  Craig B.

                                                                  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.


                                                                  Chesterfield, MA, USA

                                                                  Rates & Availability

                                                                  Additional information about rental rates

                                                                  Cleaning Fee

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

                                                                  8 Reviews
                                                                  Exceptional 5/5
                                                                  Enter dates for accurate pricing
                                                                  For booking assistance, call 888-640-7927

                                                                  Property # 606789