27 Pilgrim Road • $29,250 - $62,300

Cliff, Nantucket, MA

Located in the highly desirable Cliff area, "Pilgrim's Bliss" is an 8-bedroom, 6.2-bathroom estate offering one of the largest yard/pool/pond combinations available for lease in that area. The home offers a heated salt water pool, covered wraparound deck and integrated outdoor fireplace, multiple seating areas for lounging and dining, an expansive yard set back from the main road, and beyond the pool enclosure a winding path leads 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 18, "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, a 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 a bedroom with two twin over full size beds.

Outdoor Space

Outside, the covered porch overlooks the beautifully-manicured lawn, garden, and pool area. Additionally, there are two outdoor dining spaces and a lounge area with an integrated outdoor fireplace. An idyllic winding path leads to a small, private pond with two adirondacks to view the pond's frequent wildlife visitors, including 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

27 Pilgrim Road Location
Property Code: #2142
Bedrooms:
8 beds
Bathrooms:
6 bath and 2 half
Capacity:
18

Beds Type / Floor

King
1st
King
2nd
King
2nd
Queen + Twin +
Twin-Over-Full Bunk
2nd
Twin Bunkbed (2)
LL
King
LL
Queen
GH
Twin Bunkbed (2)
GH

Contact Agent

x
Name is required
Valid E-Mail is required
Phone is required

I agree to be conntacted by J Pepper Frazier Co via call, email and text. To opt out, you can reply "stop" any time or click unsubscribe link in the emails.

Property Amenities

Household Amenities
  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • Hair Dryer
  • Sleeper Sofa
Outdoor Amenities
  • Patio/Deck Furniture
  • Outdoor Fire Place
  • Beach Towels
  • Beach Chairs
  • Beach Umbrella
  • 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
  • Steam Room
  • Sauna
  • Yard
  • Porch
  • Patio
  • Deck
  • Parking
  • Pets Allowed
  • Private Pool
  • Central AC
  • Heat
  • Usable Fireplace
2026 Availability Sat-Sat Information contained herein is believed to be reliable but is not guaranteed.
June

06/06 - 06/13

$27,700

REQUEST BOOKING

06/13 - 06/20

$28,890

REQUEST BOOKING

06/20 - 06/27

$43,300

REQUEST BOOKING

06/27 - 07/04

$57,700

REQUEST BOOKING

July

07/04 - 07/11

$48,650

REQUEST BOOKING

07/11 - 07/18

$48,650

REQUEST BOOKING

07/18 - 07/25

$49,650

REQUEST BOOKING

07/25 - 08/01

$51,980

REQUEST BOOKING

August

08/01 - 08/08

$54,100

REQUEST BOOKING

08/08 - 08/15

$52,100

REQUEST BOOKING

08/15 - 08/22

$46,200

REQUEST BOOKING

08/22 - 08/29

$43,900

REQUEST BOOKING

08/29 - 09/05

$38,900

REQUEST BOOKING
September

09/05 - 09/12

$29,900

REQUEST BOOKING

09/12 - 09/19

$29,900

REQUEST BOOKING

09/19 - 09/26

$25,900

REQUEST BOOKING

09/26 - 10/03

$22,900

REQUEST BOOKING

Similar Nantucket Rentals
64 Cliff Road
$70,000 - $72,000 8 Beds | 8 Baths
64 Cliff Road • Cliff
#2865
16 Cliff Road
$20,000 - $30,000 8 Beds | 7 Baths
16 Cliff Road • Cliff
#3527
6 Capaum Pond Road
$50,000 - $60,000 7 Beds | 8 Baths
6 Capaum Pond Road • Cliff
#1329
72r Cliff Road
$40,000 - $50,000 5 Beds | 5 Baths
72R Cliff Road • Cliff
#1570
5 Shady Lane
$20,000 - $30,000 6 Beds | 5 Baths
5 Shady Lane • Cliff
#2601
92 Cliff Road
$30,000 - $40,000 6 Beds | 6 Baths
92 Cliff Road • Cliff
#2832
8 Derrymore Road
$13,000 - $19,600 6 Beds | 5 Baths
8 Derrymore Road • Cliff
#3148
66 Cliff Road
$30,000 - $50,000 7 Beds | 7 Baths
66 Cliff Road • Cliff
#2902
31 Pilgrim Road
$60,000 6 Beds | 5 Baths
31 Pilgrim Road • Cliff
#3361
71r Cliff Road
$30,000 - $40,000 6 Beds | 6 Baths
71R Cliff Road • Cliff
#3406
17 Sherburne...
$65,000 11 Beds | 9 Baths
17 Sherburne Turnpike • Cliff
#3596
Back to top