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10 minutes to Sugarloaf and 30 min. to Saddleback Private Setting


Property Details

Updated: Oct 19, 2016
5 BR 2 Bath Tucked away among large pines in a private off Mountain Settining

Welcome to Bentley's Place,

Nestled among large pine trees at the foot of Cranberry Peak and on Kettle Bog is your home away from home. Just 5 miles North of the Sugarloaf Access Road. Snowshoe or Cross-country ski right from the home to trails, rivers, lakes, and mountains. Minutes to Bigelow Preserve, the Appalachian Trail, Hiking, mountain biking, ITS snowmobile trails. The home features 5 bedrooms, 2 bathrooms, a kitchen, dining area, living room and laundry. This home is close to everything Sugarloaf has to offer and more. Minutes away you will find 4 restaurants 2 convenience stores and a grocery store. The Sugarloaf Outdoor Center has many spectacular x-country skiing trails and they offer skating and ice hockey events as well. Kids will love the Anti-Gravity Center where they have climbing walls, trampolines, a weight room, basketball court, etc. Cross-country skiing at Cathedral Pines and The Narrow Gauge Pathway is spectacular. You will never be bored spending your vacation at Bentley's Place.

More Details
  • Sleeps 12
  • 5 Bedrooms
  • 2 Bathrooms
  • Parking
  • Garden
  • Barbecue
  • Pets considered
  • Internet
  • Dish washer
  • Washing machine
  • Towels provided
  • Linens provided
  • Accept Credit Cards
  • Bookable online

Recent Review

About the Owner


I'm Craig and I have always loved the Sugarloaf/Bigelow area so much that I bought this wonderful place to share with others.

Call Manager
Speaks: english

8 Reviews

based on 8 traveler reviews


Great value for a big house near Sugarloaf

  • 5 of 5

We had a great time at Craig's well maintained and spacious house near Sugarloaf. I highly recommend it and hope to return again some day!

  • Submitted: Mar 1, 2016
  • Stayed: Feb 2016
  • Source: HomeAway
Owner's Response: Excellent, we want all our guests to be comfortable and happy at Bentley's Place. Hope to see you again next year... Craig E MacDonald Bentley's Place
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School vacation week February 2016

  • 5 of 5

We had a great stay at Bentley's Place. Craig & Sarah met us when we arrived to show us around (and even made Valentine cookies) . They were very nice and answered all our questions, including good places to eat. We arrived during one of the coldest weekends of the winter but were toasty warm and comfortable. My teenagers and dog loved seeing the deer come so close to the house. Would definitely go back and recommend to others. Thank you very much!

  • Submitted: Feb 26, 2016
  • Stayed: Feb 2016
  • Source: HomeAway
Owner's Response: Thank you, It was a pleasure having your family stay at Bentley's Place. We enjoy the deer very much too and hope to have you again soon. Craig E MacDonald Bentley's Place
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Comfortable and quiet escape

  • 5 of 5

We had a wonderful stay. This is a very cozy place on a great property. We had fun trecking around the nearby wilderness. The owners are great. They welcomed us in style and thought of everything we needed during our stay. Would definitely stay here again. Thanks!

  • Submitted: Feb 24, 2015
  • Stayed: Feb 2015
  • Source: HomeAway
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Quiet, beautiful and close to Sugarloaf!

  • 4 of 5

Spent the weekend at Bentley's Place for my birthday and had an absolute blast. Craig met my friends there early in the afternoon and showed the around. The house was well stocked with dishes and toiletries for all of us, and we spent so much time jumping on the trampoline and watching the deer hang out in the backyard!

Would have given 5 stars but we had a little trouble with a breaker switching off the lights/heat in our room. I think one of my friends mentioned it to him so I'm sure it will be addressed.

We will definitely be back!

  • Submitted: Jan 26, 2015
  • Stayed: Jan 2015
  • Source: HomeAway
Owner's Response: Thank you so much for staying at Bentley's Place. We were able to figure out that a defective GFI outlet was causing the breaker to trip. This was a quick fix! Thanks again, Craig E. MacDonald Bentley's Place
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What a charming place!

  • 5 of 5

We had three families stay at Bentley's Place during February vacation and had an AMAZING time! The house was clean and very charming. Everyday, we would see a herd of 15 deer come on to the property--so beautiful. It was great to be eating and watching them roam around the property to find food. The kids loved the place. They would ski all day but would still spend an hour jumping on the trampolin in the backyard.

Craig was so nice to meet us there and show us around when we first arrived. He also left us gifts of a bottle of wine and chocolate--very thoughtful. Whenever we had a question for him, he would respond to the text almost immediately.

If we go back to Sugarloaf next February vacation, we would rent Bentley's Place again. Thanks again for renting your house to us Craig!

  • Submitted: Mar 5, 2014
  • Stayed: Feb 2014
  • Source: VRBO, from HomeAway
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North Attleboro, MA

Great stay!

  • 5 of 5

We had a very relaxing stay at Bentley’s Place. The listing was accurate, home was clean, spacious and well maintained. Craig was very informative and made renting the property stress free. We spent the majority of our time at Sugarloaf Ski Area and this location was very convenient. We enjoyed the large and private yard. Only a few steps from the back door we were able to access trails to snowshoe on. Our children loved feeding and watching the deer every evening. I would definitely recommend Bentley’s Place to anyone looking to stay in the area.

  • Submitted: Feb 2, 2014
  • Stayed: Dec 2013
  • Source: HomeAway
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Rental rates

Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
2 night minimum stay

Additional information about rental rates

Cleaning Fee $100
Pet Fee $25
Refundable damage deposit $500

Manager's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.
Enter dates for accurate pricing
Total amount
Email Manager
Updated: Oct 19, 2016
Available arrival
Available stay (no arrival)


Property Type

  • house


  • Adventure
  • Family
  • Sports & Activities


  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Wood Stove ...


  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...


  • Dining ...
  • Dining Room


  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Television


  • Events Allowed
  • children welcome
  • non smoking only ...
  • pets considered ...
  • wheelchair inaccessible

Floor Area

  • 1800 sq. ft.


  • 2nd Floor - toilet, combination tub/shower, 2 Sinks
  • 1st Floor - toilet, shower


  • 5 Bedrooms, Sleeps 12
  • Stratton Brook - 1 twin/ single, Great for kids loft bed * Limit 200 lbs and air bed
  • Flagstaff - 2 twin/ single, 2 Singles
  • Canberry Peak - 1 queen, Room for air bed on floor
  • Kettle Bog - 1 queen, Room for air bed on floor
  • Dead River - 1 queen, Room for air bed on floor
  • Room for air bed on floor


  • Bicycles
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill


  • Guests provide their own meals

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