27 Pilgrim Road Nantucket • Cliff • $25,900 - $53,900

27 Pilgrim Road Nantucket Rental Thumb 1 27 Pilgrim Road Nantucket Rental Thumb 2
27 Pilgrim Road Nantucket Rental Thumb 3 27 Pilgrim Road Nantucket Rental Thumb 4
27 Pilgrim Road Nantucket Rental Thumb 5 27 Pilgrim Road Nantucket Rental Thumb 6
27 Pilgrim Road Nantucket Rental Thumb 7 27 Pilgrim Road Nantucket Rental Thumb 8
27 Pilgrim Road Nantucket Rental Thumb 9 27 Pilgrim Road Nantucket Rental Thumb 10
27 Pilgrim Road Nantucket Rental Thumb 11 27 Pilgrim Road Nantucket Rental Thumb 12
27 Pilgrim Road Nantucket Rental Thumb 13 27 Pilgrim Road Nantucket Rental Thumb 14
27 Pilgrim Road Nantucket Rental Thumb 15 27 Pilgrim Road Nantucket Rental Thumb 16
27 Pilgrim Road Nantucket Rental Thumb 17 27 Pilgrim Road Nantucket Rental Thumb 18
27 Pilgrim Road Nantucket Rental Thumb 19 27 Pilgrim Road Nantucket Rental Thumb 20
27 Pilgrim Road Nantucket Rental Thumb 21 27 Pilgrim Road Nantucket Rental Thumb 22
27 Pilgrim Road Nantucket Rental Thumb 23 27 Pilgrim Road Nantucket Rental Thumb 24
27 Pilgrim Road Nantucket Rental Thumb 25 27 Pilgrim Road Nantucket Rental Thumb 26
27 Pilgrim Road Nantucket Rental Thumb 27 27 Pilgrim Road Nantucket Rental Thumb 28
27 Pilgrim Road Nantucket Rental Thumb 29 27 Pilgrim Road Nantucket Rental Thumb 30
27 Pilgrim Road Nantucket Rental Thumb 31 27 Pilgrim Road Nantucket Rental Thumb 32
27 Pilgrim Road Nantucket Rental Thumb 33 27 Pilgrim Road Nantucket Rental Thumb 34
27 Pilgrim Road Nantucket Rental Thumb 35 27 Pilgrim Road Nantucket Rental Thumb 36
27 Pilgrim Road Nantucket Rental Thumb 37 27 Pilgrim Road Nantucket Rental Thumb 38
27 Pilgrim Road Nantucket Rental Thumb 39 27 Pilgrim Road Nantucket Rental Thumb 40
27 Pilgrim Road Nantucket Rental Thumb 41 27 Pilgrim Road Nantucket Rental Thumb 42
27 Pilgrim Road Nantucket Rental Thumb 43 27 Pilgrim Road Nantucket Rental Thumb 44
27 Pilgrim Road Nantucket Rental Thumb 45 27 Pilgrim Road Nantucket Rental Thumb 46
27 Pilgrim Road Nantucket Rental Thumb 47 27 Pilgrim Road Nantucket Rental Thumb 48
27 Pilgrim Road Nantucket Rental Thumb 49 27 Pilgrim Road Nantucket Rental Thumb 50
27 Pilgrim Road Nantucket Rental Thumb 51 27 Pilgrim Road Nantucket Rental Thumb 52
27 Pilgrim Road Nantucket Rental Thumb 53 27 Pilgrim Road Nantucket Rental Thumb 54
27 Pilgrim Road Nantucket Rental Thumb 55
Rent Now

Nantucket Rentals

Bedrooms:
8 beds
Bathrooms:
6 bath and 2 half
Capacity:
20

Beds Type / Floor

King
1st
King
2nd
King
2nd
Queen + Twin/Full Bunk + Twin
2nd
Twin Bunkbed(s)
LL
King
LL
Queen
GH
Twin(s)
GH
Rental ID: #2142 Nantucket STR Registration: #C0065071970

27 Pilgrim Road, Nantucket, MA

Located in the highly desirable Cliff area, "Pilgrim's Bliss" is an 8-bedroom, 6.2-bathroom estate with a heated salt water pool, covered wraparound deck with an integrated outdoor fireplace, multiple seating areas for lounging and dining, an expansive yard set back from the main road, and a whimsical, flower-lined path leading to a private duck pond. With its close proximity to many island favorites, in addition to the property's expansive offerings, including a sleeping capacity of 20, "Pilgrim's Bliss" is ideal for extended, multi-generational families with varied interests and leisure pursuits.

First Floor Description

The first floor of the main house offers an open layout with a fully-equipped kitchen featuring high-end appliances and a large center island with seating for six. Adjacent to the kitchen is a dining area that accommodates 14, a powder room, and a brightly-lit living space with plenty of comfortable seating, a wall-mounted Smart TV, a wood-burning fireplace, and two ways to access the wraparound deck and pool area. Completing the first-level is a king bedroom with dedicated office space, private deck access, and en-suite bathroom with double vanity sinks and walk-in shower.

Second Floor Description

The primary bedroom is situated on the second level, offering private balcony access, king size bed, and an en-suite bathroom with double-sink vanity and walk-in shower. Two additional bedrooms are located on this floor, both with en-suite bathrooms; one with a king bed, the other with a free-standing queen bed, twin bed, and twin-over-full bunkbed.

Lower Floor Description

The lower level features a large media room, which can also be used as a children's play room, a full hallway bathroom, and two guest bedrooms; one with two twin bunkbeds, the other with a king bed.

Cottage

The two-story guest house is situated just behind the main house, directly in front of the pool, offering convenient living and sleeping quarters for extended family and guests, an au-pair, private chef, etc. The main level of the guest house can be accessed from the pool terrace doors, where guests are met with an open dining/living area, a convenient powder bath, and a well-stocked kitchen with a breakfast bar for four. The second level offers a shared full bathroom with tub/shower combo, one bedroom with a queen bed, and one bedroom with two twin beds.

Outdoor Space

Outside, the covered porch overlooks the beautifully manicured lawn, garden and pool area, and also features two outdoor dining spaces, a lounge area with an integrated outdoor fireplace surrounded by able seating. An idyllic flower-lined path with strung lights leads to a small, private pond with a seating area to view the pond's frequent wildlife visitors, which includes geese, ducks, turtles, bullfrogs, and white egrets.

Distance to Town: 1.2 Miles to Main Street

Distance to Beach: 0.7 Miles to Steps Beach

Household Amenities

  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • Hair Dryer
  • Sleeper Sofa

Outdoor Amenities

  • Patio/Deck Furniture
  • Outdoor Fire Place
  • Beach Towels : Y - 15
  • Beach Chairs : Y - 8
  • Beach Umbrella
  • Bicycles
  • Gas BBQ
  • Outdoor Shower

Kitchen Amenities

  • Gas Stove
  • Microwave
  • Dishwasher
  • Toaster
  • Blender
  • Mixer
  • Coffee Maker (drip)
  • Keurig
  • Food Processor
  • Lobster Pot

Electronic Amenities

  • Wi-Fi
  • TV
  • Smart TV
  • Cable Television
  • Sonos

Property Amenities

  • Steam Room
  • Sauna
  • Steam Room
  • Yard
  • Porch
  • Patio
  • Deck
  • Parking : Y - 1
  • Private Pool
  • Central AC
  • Heat
  • Usable Fireplace
2025 Availability Sat-Sat ( Information contained herein is believed to be reliable but is not guaranteed. )
June
06/07 - 06/14 $26,500
06/14 - 06/21 $31,970
06/21 - 06/28 $41,970
06/28 - 07/05 $53,900 RENT NOW
July
07/05 - 07/12 $48,650 RENT NOW
07/12 - 07/19 $48,650 RENT NOW
07/19 - 07/26 $49,850 RENT NOW
07/26 - 08/02 $49,980 RENT NOW
August
08/02 - 08/09 $52,100 RENT NOW
08/09 - 08/16 $45,800 RENT NOW
08/16 - 08/23 $44,500 RENT NOW
08/23 - 08/30 $35,900 RENT NOW
08/30 - 09/06 $32,900 RENT NOW
September
09/06 - 09/13 $28,900 RENT NOW
09/13 - 09/20 $28,900 RENT NOW
09/20 - 09/27 $25,900 RENT NOW
09/27 - 10/04 $25,900 RENT NOW

*Rates must be confirmed before booking and do not include state and local taxes, which are currently 11.7%.

Similar Nantucket Rentals

Back to top