Wiley's Way

United States / Massachusetts / Gloucester

This charming cottage is located on a quiet side street in the fabled artist colony of Rocky Neck in East Gloucester.

up to 2
up to 4
Min. Nights Upon Request


Enter the front door into the comfy and cozy front parlor which is nicely furnished and is the perfect place to relax, listen to music or read a book. Beyond the parlor, at the rear of the house, is the spacious living room room, with cathedral ceilings and exposed beams. This open-plan space includes a well-equipped galley kitchen and dining table along one end of the room.

Outside of the great room is a lovely private garden area, perfect for al fresco dining for four. There is also a full bath on this level. Upstairs are two bedrooms and a full bath with separate shower and jetted tub. Walk out the garden gate to enjoy the charming seaside restaurants, theater, galleries and quaint shops of historic Rocky Neck.


2 Bedrooms, 2 Bathrooms

Sleeps 4 Guests

  • Heating
  • Air Conditioning
  • Washer/Dryer
  • Iron/Ironing Board
  • Coffee Maker
  • Fully Equipped Kitchen
  • Blender
  • Kettle
  • Al Fresco Dining
  • Fireplace
  • Gas Grill
  • Television
  • Desk with Chair


Bedroom Details

Bedroom One: Queen Bed, TV
Bedroom Two: Queen Bed

Beach Details

Long Beach: 3 miles
Gloucester Public Beach: 3 miles
Wingaersheek Beach: 8 miles
Crane Beach: 15 miles
Good Harbor Beach: 3 miles

Location Details

Boston Logan International Airport: 37 miles
Portsmouth International Airport: 65 miles
Manchester Boston Regional Airport: 72 miles
Stage Fort Park: 3 miles
Restaurants and Shops: 2 miles
7 Seas Whale Watch: 2 miles
Eastern Point Lighthouse: 2 miles
Bass Rocks Beach Club: 2 miles
Halibut Point State Park: 7 miles
Cape Ann Golf Course: 11 miles
Bass Rocks Golf Club: 2 miles
Castle Hill on the Crane Estate: 15 miles
Gloucester: 2 miles
Salem: 18 miles
Boston: 41 miles

Villa Notes

Dogs allowed (pet fees apply)
No smoking, events or parties allowed


Travel Dates Bedrooms Min. Night Stay Nightly Rates
April 01, 2023 - May 27, 2023
2 3 $ 469 *
May 28, 2023 - September 18, 2023
2 3 $ 547 *
September 19, 2023 - November 01, 2023
2 3 $ 469 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Tax Service Charge Details *

Guest Services Fee - US $291

Security Deposit Details

Damage Fee - US $129

Minimum Stay Details

Minimum stay 3 nights

Accidental Damage Waiver

A $99 Accidental Damage Waiver applies to every reservation.

Exclusive Offers

Take your vacation to the next level, with 2 free airline tickets.* For a limited time, every reservation over $50,000 will receive an airline reimbursement worth up to $1,000 - any airline, any destination. Imagine flying in style to your handpicked villa located in one of the most beautiful destinations around the world, knowing that you've saved on the cost of your flights. This is your chance to experience the ultimate in luxury travel and indulge in the vacation of a lifetime.

*Free air promotion is valid new bookings only and cannot be applied to existing bookings. Valuation based on two round trip tickets using the bureau of Transportations U.S. average flight price for 2022. Receive up to a $1,000 reimbursement for flights upon presentation of a flight receipt. Minimum booking value of $50,000 applies. The booking value applies to the villa cost only and does not include any additional services or fees. This offer is valid for bookings made 2/20/2023 through 4/02/2023 for travel now through 12/31/2024. Bookings made outside of this period will not be eligible. The $1,000 air credit offer is non-transferable, has no cash value, and cannot be redeemed for any other service. The airline credit will be applied to your booking once your villa rental has been paid in full. The airline credit will be redeemed by providing a receipt of your booked flight and a check will be sent to you within 15 business days of providing flight documentation. All offers are subject to availability. We reserve the right to modify or cancel this promotion at any time without notice.


*Please contact us for availability.


Villa information may change without notice and should be confirmed with our villa rental specialists.