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Nantucket Summer Rental Property

Middle Bear
114 Cliff Road,
Nantucket MA 02554

Only available in June, Sept and October – Click here to make reservations.

Contact Eric for inquiries

Located one mile East of town and practically next door to the private Westmoor Club, "Middle Bear" is a five minute walk to Hinckley Lane beach and right on the new bike path to Madaket. Owned by the Holch family since the early 1950's, "Middle Bear" has 4 bedrooms, 2 bathrooms, an old fashioned kitchen with counter and 6 stools, large living room with cathedral ceiling and a dining area that seats 10 with a small sitting area with fireplace. House is sort of divided with 3 bedrooms in the South end served by one bathroom, and the 4th bedroom is at the North end of the house and uses the second bathroom off the kitchen. This is summer vacationing circa 1950. No lap pools, no air conditioning, no Jacuzzi's, no marble bathrooms, no Viking stoves or Subzero refrigerators. (We do now have wifi and a flat screen TV). But it has a large lawn for playing games, an outdoor shower to clean off after the beach, lots of mix-matched beach towels and beach chairs and a great living room to sit and talk and visit with your family and friends.

Middle Bear & front lawn area
faces west with a great lawn, lawn chairs and sunset views

Back side of house has outdoor shower area and back lawn/picnic table

Living Room with cathedral ceiling

Living Room looking into Dining/Sitting area

Living Room looking at the front door

Dining Area

Dining Room

View from Dining area towards small sitting area/fireplace/TV


Kitchen area facing east, back hall is to left

Kitchen 2

Kitchen area facing West into Living Room


Back Hall with Washer/Dryer and Bathroom #2 off to left

Master Bedroom

Master Bedroom has window A/C unit

Bathroom 1

Bathroom #1 with tub/shower serves MB, Bedroom #2 & 3 in South end of house


Bedroom #3


Bedroom #4 in North end of house, off dining area

Bathroom 2

Bathroom #2 with shower stall


A Little "Middle Bear" History

In the late 1940's Gladys Wood, a prominent real estate broker on the island, bought the clubhouse of the defunct Nantucket Golf Club (yearly dues in 1935 were $50) and part of the 18th hole. She moved the Mens and Womens Locker Room wings off the main clubhouse, added kitchens and created 3 rental properties which she called "Big Bear", "Middle Bear", and "Little Bear". Today "Big Bear" is the headquarters of the Nantucket Conservation Foundation, "Middle Bear" is at 114 Cliff Road, and "Little Bear" has been moved but can still be seen as the little guesthouse at 116 Cliff Road. Only "Middle Bear" still retains its given name from the 1940's.

After renting "Big Bear" in 1950, the Holch family bought the neighboring "Middle Bear" to be their island summer home. Much of the house remains pretty much exactly as it did in 1950, although the "new" living room and a little bedroom was added in the late '60's and the "wart" off the back added a second bathroom/shower and a washer/dryer. Golf cleat marks can still be seen in the thresholds throughout the house. It has remained in the Holch family continuously since 1950 and has seen 4 generations of families enjoying the simple pleasures of an old, quirky island summer cottage.

Only available in June, Sept and October – Click here to make reservations.