check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar


Member since: 2012
Speaks english, french

Luxury 8br 7ba Home, Pool+Guest House, Old World Charm & Modern Comforts

13 Reviews
Bedrooms 8
Half Baths2
Property type estate
Minimum Stay 3 - 7 nights


Photos and Description of this Cliff holiday estate

8 bedrooms, 7 baths, sleeps 16

A favorite for wedding groups & multi-generational families, 'Pilgrim's Bliss' is located off of Cliff Road, which starts from town and runs parallel to the cliff side beaches, beach clubs and restaurants. The Cliff Road residential section is one of the most desirable areas on the island. 'Pilgrim's Bliss' has consistently garnered extraordinary reviews by renters, including a recent resident who has a long history of renting other top end homes on the island, indicating it was by far the best home where they stayed over the years. This warm, welcoming family home with a salt water, heated swimming pool and guest house sits on the edge of town and is located a two minute drive to the center, a short walk to Step's Beach and one street away from the restaurants and tennis courts of the popular Westmoor Club. Pilgrim's Bliss offers easy access to shops, restaurants and beaches, while having the benefits of quiet, privacy, a large back yard with a duck pond beyond, guest house, swimming pool and star filled skies. There are the comforts of the extra large, burnished leather Chesterfield sofa, classical themed arm chairs and dining table constructed of 100 year old planks that can seat up to 14, to the extensive range of books, playroom, children's games, 3 plasma TV's (two are 3D large format), extra large covered wrap-around porch with distinct areas, including outdoor living area with fireplace, dining area, breakfast table, Sonos internet radio, steam room and air conditioning. At night, sit on the porch and look through the astronomical telescope at skies exploding with stars, or wander down to the duck pond, along the private, flower filled path lined with low level, white Christmas lights and enjoy a glass of wine while reclining in the Adirondack chairs.

  • children welcome
  • non smoking only
  • suitable for elderly or infirm
  • wheelchair inaccessible
Owner (Owner)
Member since: 2012
Speaks english, french

Guestbook comments from the owner

excerpt from guestbook. "Wonderful holiday for the family 20th celebration. Look forward to returning. Thanks to the owner - a wonderful facility for all the kids."
Aug 2012
  • 1 of 4


based on 13 traveller reviews

Luxury 8br 7ba Home, Pool+Guest House, Old World Charm & Modern Comforts
average rating of 5.0 based on 17 reviews

Perfection on Nantucket

  • 5 of 5

Pilgrim's Bliss is aptly named . . . the home is impeccable yet comfortable, close to town yet serene, spacious yet warm . . . we couldn't have asked for more! I rented the home for a group of 12 women and we were impressed with everything from the decor to the landscaping to the enviably outfitted kitchen! Our group so loved the back deck fireplace, and we spent hours chatting and visiting in this beautiful space. The beds were incredibly comfortable, the showers luxurious and the proximity to Steps beach and Something Natural made for easy and fun walking excursions for sandwiches and sunshine . . . so perfectly Nantucket! Working with the owner was a dream, and we can't wait to book this piece of heaven again. We had high expectations going in, and they were surpassed. Well done!

  • Review Submitted: Sep 24, 2016
  • Date of Stay: Sep 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

Gorgeous Property ideally located!

  • 5 of 5

This is a gorgeous manicured property, located about a mile from Nantucket village and about 1/2 mile to Stepps beach which was ideal for my young grandchildren. The House was spotlessly clean, spacious, with beautiful architectural details and all the amenities of home. Each bedroom had a very large bathroom for optimum privacy. We loved the attached guest house which was just as charming as the main house. Sitting by the pool in the evening provided a nice way to wind down after a busy day of touring, biking, swimming. When we dined in, it was always on the large outdoor porch that accommodated our 14 family members. Fun to be all together! We loved the local bakery, "Something Natural" which was a short walk or bike ride away-delicious home made breads and pastries, plus sandwiches for lunch. A safe bike path was right across the street from Pilgrim Rd, so we felt very comfortable allowing the children to ride. Nearby Barlett Farms provided us with delicious fresh produce and cheeses. I guess I can just sum this up by saying this property is on the top of the list of our favorite annual family vacations. From 8 to 80 years old, there was something for everyone to do and enjoy.

  • Review Submitted: Aug 17, 2016
  • Date of Stay: Aug 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

Terrific, Wonderful, Magical...

  • 5 of 5

What a terrific, wonderful, magical place this is! We had a suberb stay and already can't wait to come back! So many blissful new memories for our family - our youngest son lost his first tooth here!! Thanks for the hospitality and the beautiful vacation setting!

  • Review Submitted: Aug 12, 2016
  • Date of Stay: Jun 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

ACK Christmas Stroll

  • 5 of 5

This was our first trip to Nantucket for Christmas Stroll & our first time at Pilgrim's Bliss. What a wonderful experience. The house made you feel like you had come home the minute you walked in the door. Every convenience & amenity was thought of (my personal favorite was the bathrobes!!). An absolutely magical experience. We would love to come back again.

  • Review Submitted: Dec 18, 2015
  • Date of Stay: Dec 2015
  • Source: HomeAway
Did you find this review helpful?
1 0

We are rarely at a loss for words

  • 5 of 5

We are rarely at a loss for words, but... here are two: THANK YOU. Bliss, indeed, also relaxing, warm and elegant come to mind. The greatest gift a family can share is time together. Thank you for letting our family share time in your wonderful home! We particularly love the exotic wooden chair (at the front door) and all the interesting art. "Pilgrims Bliss" is aptly named. With deepest appreciation

  • Review Submitted: Aug 2, 2015
  • Date of Stay: Jul 2015
  • Source: HomeAway
Did you find this review helpful?
0 0

Late Spring at Pilgrim's Bliss

  • 5 of 5

Start with amazing architectural features , add impeccable yet comfortable furnishings and an energetic , responsive "on Island " manager , toss in an immaculate modern kitchen with every imaginable cooking utensil , immediately adjacent to an expansive living room and dining area , surrounded by a wrap around porch with over stuffed chairs, outdoor fireplace , nice size yard and heated pool , walk past the multiple free bicycles, then open the back yard fence and stroll down to the pond with its Adirondack chairs. At this juncture , whoever you invited to join you , even before they have seen the beautifully furnished bedrooms (each with its own bathroom ) the downstairs rec room or the self contained pool house (with separate kitchen and laundry ) will be moving you up on their holiday gift list. My family stayed @ Pilgrim's Bliss for the joyous occasion of our son's wedding to a lovely young lady who had summered on Nantucket for years. As noted in the guest book upon our departure , "the Bliss" took a special week to a whole new level . The listing pictures and description are totally accurate, the actual experience is even better.

  • Review Submitted: Jun 19, 2015
  • Date of Stay: May 2015
  • Source: HomeAway
Did you find this review helpful?
1 0


Car: not necessary

Pilgrim's Bliss is located just off Cliff Road, one of the most exclusive areas of Nantucket, a stones throw from the popular Westmoor Club, 5 minutes walk to Step's Beach, 1 minute drive to the Something Natural sandwiches/picnic area, and a 2 minute drive to town


Rates & Availability

Rental Rates for this holiday estate in Cliff, Massachusetts

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Memorial Day/Figawi 2017
25 May 2017 - 29 May 2017
3 night minimum stay
May 30-Jun 3,2017
30 May 2017 - 3 Jun 2017
3 night minimum stay
June 3-10, 2017
4 Jun 2017 - 10 Jun 2017
3 night minimum stay
June 10-17, 2017
11 Jun 2017 - 16 Jun 2017
6 night minimum stay
June 17-24, 2017
17 Jun 2017 - 23 Jun 2017
7 night minimum stay
June 24-July 1, 2017
24 Jun 2017 - 30 Jun 2017
7 night minimum stay
July 1-8, 2017
1 Jul 2017 - 7 Jul 2017
7 night minimum stay
July 8-15,2017
8 Jul 2017 - 14 Jul 2017
7 night minimum stay
July 15-22, 2017
15 Jul 2017 - 21 Jul 2017
7 night minimum stay
July 22-29, 2017
22 Jul 2017 - 28 Jul 2017
7 night minimum stay
July 29-Aug 5, 2017
29 Jul 2017 - 4 Aug 2017
7 night minimum stay
Race Week, Aug 5-12, 2017
5 Aug 2017 - 11 Aug 2017
7 night minimum stay
Aug 12-19,2017
12 Aug 2017 - 18 Aug 2017
7 night minimum stay
Aug 19-26, 2017
19 Aug 2017 - 25 Aug 2017
7 night minimum stay
Aug 26-Sep2, 2017
26 Aug 2017 - 1 Sep 2017
7 night minimum stay
Labor Day, Sep2-9, 2017
2 Sep 2017 - 8 Sep 2017
7 night minimum stay
Sep 9-16, 2017
9 Sep 2017 - 15 Sep 2017
3 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

Refundable Damage Deposit A$3,947

There is a specific contract that both parties must sign. There is an allowance for propane usage (primarily used by the pool heater).

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates to see total
Send a Message
Available arrival
Available stay (no arrival)


Accommodation and facilities for this holiday estate rental in Cliff, Massachusetts

Property Type:
  • estate
  • Guests provide their own meals
  • Air Conditioning
  • Alarm Clock
  • Clothes Dryer
  • Fireplace
  • Firewood
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Parking
  • Parking Off Street
  • Parking On Street
  • Security System
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • fax
  • 4 Ring Stove
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Lobster Pot
  • Microwave
  • Oven
  • Refrigerator
  • Toaster
  • Dining Room
  • seating for 16 people
  • 6 Bathrooms
  • 2 Half Baths
  • Bathroom 1 - toilet , bath with shower
    Bathroom 2 - toilet , shower enclosure
    Bathroom 3 - toilet , bath with shower , jacuzzi
    Bathroom 4 - toilet , shower enclosure
    Bathroom 5 - toilet , shower enclosure , Steam room
    Bathroom 6 - toilet
    Bathroom 7 - toilet , bath with shower
    Bathroom 8 - toilet
  • Steamroom in basement bathroom
  • 8 Bedrooms, Sleeps 16
  • Bedroom 1 - 1 extra lg. double bed
    Bedroom 2 - 1 extra lg. double bed
    Bedroom 3 - 4 child bed , Bunks
    Bedroom 4 - 1 sofa bed/futon , Queen Firm Sofabed
    Bedroom 5 - 1 large double bed
    Bedroom 7 - 1 large double bed
    Bedroom 8 - 2 single bed , Sofabed
    Bedroom 6 - 1 sofa bed/futon , Playroom Sofabed
  • Books
  • books - fiction/non-fiction
  • books - kids
  • CD Player
  • DVD Player
  • Game Room
  • Games
  • Music Library ...
  • Satellite / Cable
  • Stereo
  • Television
  • Toys
  • Balcony
  • Barbecue
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • veranda
  • wooden decking
  • 8 garden chairs
  • 4 beach chairs
  • children welcome
  • non smoking only
  • suitable for elderly or infirm
  • wheelchair inaccessible
Pool / Spa:
  • Heated Pool
  • Outdoor Pool
  • Private Pool ...
  • Whirlpool
  • bay
  • churches
  • cinemas
  • library
  • museums
  • playground
  • pond
  • restaurants
Leisure Activities:
  • antique hunting
  • beachcombing
  • horse riding
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • hiking
  • pier fishing
  • sailing
  • bay fishing
  • surf fishing
  • surfing
  • swimming
  • wind-surfing
Steam room in basement bathroom