Nantucket Rentals
Beds Type / Floor
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

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%.